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Our Travel Story > How to Travel the World for 5 Years: A Remote Life Adventure

March 28th, 2023 marked the day that we had officially been traveling the world for FIVE FULL YEARS, something we’ve been able to afford mostly by using investment dividends, transitioning into a remote coding job, and spending most of our time in countries with a low cost of living.

Last year, we wrote about our fourth year traveling the world, and we did the same for years three, two, and one - and now we are back to let you know how the fifth year went - traveling with a 4-year old and a 2-year old, moving through the last months of Covid restrictions, and increasing our budget to about $2,250/month!

This is what life is like while traveling the world as a family with 2 littles.

We were late on this year’s article as we have some rather exciting news to share with you later in this article. However we're also making this years article more of a “how to do it yourself” - using our experiences and mishaps to make it easier on you than it was for us - in addition to it being a summary of what we’ve learned over our adventures this last year. We hope you like it!

We left off in the last article in Colombia, with the intention to explore the main area of Medellín and then head off to a coffee farm in Costa Rica for a month after that. Our potential paths for this year were:

1. Taking a break and starting a career in Hawaii or New Zealand

2. Teaching English in Japan, South Korea, or China

3. Or exploring more of Latin America

We were saying that we weren’t really sure where we’d end up in the long run, and didn’t have a clear path forward at that point.

Some of you might also be at a crossroads in your life: simply trying to justify if you should keep doing what you’ve been doing or if you should change it up and get into a better situation. We get it, it was hard for us to leave our jobs at Disney in early 2018 that we loved so much. It might have been easier if we didn’t like those jobs, but we knew that time was going to pass whether we made the decision or not - and that our clock is always counting down. So, we wanted to do it before it was too late. You know, before we kick the bucket, before it's too late.

But, it’s not easy being in a situation where you aren’t sure how things will turn out - or even where you'll be a year from now. So, if you’re in that phase of your life, we get it because we feel like we’ve been living that way over the last few years now. The good news is that it turns out, and that we’ve learned how to make that happen quicker.

So, what did we end up doing this year? We start off this article with our last month exploring the main area of Medellín, Colombia.

Below is our emotional - and exciting - journey over our fifth year of traveling the world - but you can skip to our highlights and lessons learned near the bottom if you’d prefer a shorter read.

Our Final Month in Medellín, Colombia

Our flights into the States early in 2022 put us behind budget, so we tried to save a lot of money in Medellín by booking a couple very affordable places to stay. Although our first place in Envigado was amazing, and while there are other lovely areas of Medellin as well, like any city there are some not so nice areas too. In our last few weeks in Medellín we ended up booking a fairly affordable Airbnb near the center of the city that had all 5-star reviews.

When we checked in, we were told not to go out at night and not to walk around with our cell phones out as it wasn’t safe. Plus, it turned out to be infested with bugs! It was also a holiday weekend, so most places were fully booked up. It took us a couple of days to find a new place to move into. Luckily we found another place back in Envigado. It was really stressful at the time, but that experience has provided for this one piece of advice to fellow travelers: Stay in Envigado.

Envigado has trees along the streets, and is lovely for bird-watching. It is a peaceful and quiet neighborhood. Nearby, a large mall called “Vivo Envigado” has a huge play area for kids. Yes, there are plenty of cars in this area because it is still part of the city, but the streets were safe and we could walk around at night without any worries. The Pan de queso and Marinera Paellas were delicious, and we also ate some of the best plant-based burgers we’ve ever tried - if you’re ever in Colombia, definitely try the Pietran brand burgers!

After getting settled in, we did end up exploring the main area of Medellín over the course of a few weeks, and we took a trip out to El Peñol and Guatape while we were there. Guatape is highly recommended! A few of our other favorites were Parque Explora, La Casa de las Piedritas, Parque Arví, Pueblito Paisa, Comuna 13 and Las Escaleras, and Plaza Botero. We talk more about those places, and a few others that we visited in this article:

• The Entrepreneur-Friendly Transformed City of Medellín - Colombia

Our impression of Medellín, Colombia is that we really enjoyed living in the city for a few months. It was a city engulfed by nature with plenty of delicious food and things to do. However, we only saved a little bit each month by living here as we did explore a bit more than expected. That being said, we would certainly go back again!

Staying at the Coffee Farm in Costa Rica’s Mountains

Slowing down again from our two weeks of exploring Medellín, we headed straight for the mountains of Costa Rica where we spent a month basically relaxing on a coffee farm. Point in case while traveling the world is that you’ll get exhausted from constantly exploring (known as “fast-travel”), especially if you have small children along with you! You’ll definitely need to build in some time to get work done and relax, and this was our time to do that. In fact, we even hired a nanny, a friend of our host, to watch our children for a few hours per day, about three days per week. It was incredibly worth it.

When we read about Costa Rica we learned that most people absolutely needed to have their air conditioning to survive (not literally, but that’s how they made it sound). Staying in the mountain region in May is quite a bit different, it was very chilly at night and in the mornings - plus there were a large amount of flying insects out after sunset as well. We always closed the doors, but if you know anything about areas with flying insects you’ll also know that there are plenty of spiders around to catch those flying insects as well. So, we did have to manage a number of those during our stay at the coffee farm.

That being said, the days were absolutely gorgeous and the air was incredibly clean. We could see down into the city, and across the mountains. Not only was it an organic coffee farm, but they also had six chickens in a large coop nearby, so our hosts always delivered fresh eggs to our place.

We managed to get some work done when the nanny was around, and even relax a bit while we were there. Plus, Bradley also got bold enough to apply to a Finance Administrator role at Victoria University of Wellington in New Zealand. He didn’t get selected for the role, but it got us thinking about potentially slowing down a bit more. Shortly thereafter, Bradley also talked with an immigration advisor to see if it was a real possibility - but it seemed that having a job offer was the key and we didn’t have one.

La Fortuna, La Paz, and the San Jose Area of Costa Rica

After a few weeks of eating deconstructed Gallo Pinto - the local dish which consists of fried plantains, white rice, black beans, and fried eggs - we were visited by Bradley’s mother, who came down to see the kids for her birthday. An explorer herself, she wasn’t in the mood to just sit around.

So, we ended up having another week of adventures, starting with a day trip out to the Poás Volcano, which gave an incredibly high perch for looking into the entire volcano crater, and the La Paz Waterfall Gardens Nature Park, which was filled with beautiful tropical flowers, hummingbirds, a variety of animals, and a number of waterfalls. Unfortunately for us, it began to rain just as we were doing the waterfall trek and we had no idea that there were so many stairs to walk up and down the cliffside to see all of the waterfalls. We got absolutely soaked as the rain poured down and almost missed the bus at the end to get back to the park entrance! It was exhausting for sure, but we loved seeing those majestic waterfalls.

Next we took trip up to La Fortuna that included a delicious meal at the Rancho Perla Restaurant (aka SelvaRustica), a hike down to see the Catarata Río Fortuna (waterfall), dinner and relaxation at the hot pools of Ecotermales Fortuna, and a hike through the Mistico Arenal Hanging Bridges. Let’s just say that these were not “stroller-friendly” places to visit, but we would definitely do the Hanging Bridges and Ecotermales again. We'll have an article about those places soon.

After getting back from that trip, we decided to look for the Tesoro Escondido waterfall, but we ended up stopping at a different waterfall altogether - the Rio Agrio Waterfall - which had a “Dino Land” as well. This stop was definitely worth the trip - especially for the kids! The natural landscape of this region made the backdrop look just like “Jurassic Park” for all of the dinosaurs. It really was incredible, and the path to the waterfall felt like we were literally in Jurassic Park. Amazing area, great surprise!

You can learn a bit more about some of the other places we stopped in this article we wrote about the San Jose area of Costa Rica. We all had a wonderful time exploring and spending time with “Grandma Betty.”

Exploring Rio Celeste, the Cloud Forest, and Manuel Antonio Park

A week more of relaxation at the coffee farm, and then we were off for another week long adventure ourselves - all the way past La Fortuna and up to Rio Celeste. We had heard about the Cavernas de Venado, and wanted to go on our way out there, but small children weren’t permitted due to tight spaces in the caves. Oh well!

Rio Celeste is a magically light-blue colored waterfall and pool at the end of a hike - super gorgeous and definitely worth the stop if you’re in this region of Costa Rica.

The next morning we stopped at the Catarata Llanos del Cortés, which was kind of like a secluded beach island in the middle of the forest surrounded by waterfalls, on our way out to Monteverde for a night safari in the Cloud Forest. The kids were super quiet as we walked around in the dark using the flashlights to spot different bugs and animals in the forest - but they absolutely loved it. We got to explore some more of the cloud forest the following day with our visit to the Reserva Bosque Nuboso Santa Elena, a much more affordable option with similar features to the Cloud Forest Biological Preserve.

From there, we headed south and stopped at a crocodile bridge and a nearby park - that had poison dart frogs jumping around all over the place - on our way out to Manuel Antonio National Park. All of our friends that had spent time in Costa Rica recommended for us to visit Manuel Antonio to see all of the wildlife, so we made it a point to go. We did manage to see a single sloth climbing a tree near the cafe there, as well as a good number of crabs and a variety of wild monkeys, but less than we expected based on the hype we received. That being said, we’d still recommend walking the trails as there were beautiful sights everywhere and it was fun looking for all the animals!

More Relaxation in San Jose, and then a Daycare…

After that week we pretty much stayed low at a different place in San Jose for the rest of our time in Costa Rica as we needed to catch up on work again, save some more money, and relax. You might not know it based on all the talk about how affordable Costa Rica is, but it’s actually the MOST expensive Latin American country, and nearly as expensive these days as the United States - unless you are a local - so it did a number on our already overly extended budget!

“Costa Rica felt incredibly like Dominica, only slightly more developed and significantly more expensive.” - Bradley

We also learned about a new potential remote-work job option that Jenny decided to pursue: Remote Bookkeeping. She even became certified Quickbooks ProAdvisor. However, after getting the certification we learned that this was not really an option for us (we ended up writing a bad review for “Booming Bookkeeping Business”) as we’d have had to start our business while living in the USA - and possibly opening a physical office location - so, as they eluded to it being possible, it was actually a waste of money. There are others, like teaching English online, that still work quite well though.

In other news, while working on our travel blog, we ended up finding a deal for all of us to fly back to New Zealand for just under $1,400 total - in February of 2023 on JetStar - so we booked it. You can tell that we were really thinking a lot about New Zealand, even after just exploring some really amazing places in Costa Rica.

As work was piling up from all of our adventuring, and with the kids absolutely wanting every minute of our attention, we decided to enroll them in a preschool / daycare for the last 2-3 weeks to give us time to work. It was amazing to actually have time to ourselves to work again - it honestly felt great. The kids started on a Thursday and went back on Friday, both enjoying their first time at “school,” but that weekend things changed for us.

We all came down with an epic case of Ebola - or at least that is how it felt! We think it was actually RSV, but it completely incapacitated all of us for 2 full weeks - we even ended up going to the Children’s Hospital ER at one point, which is free in Costa Rica and likely would have cost us a small fortune in the US, but they said it wasn’t Ebola and that we’d recover with a few medications. Hard to believe! Anyway, we didn’t get any more work done and they didn’t spend any more time at the daycare.

We all finally recovered about 2 weeks later and then left Costa Rica on our way to Mexico City, feeling healthier and hopeful.

A Few Days in Mexico City, a Few Months in Cuernavaca

Researching Mexico City beforehand helped us choose the La Condesa area for a few days. It was a wonderful spot that felt quite safe and even had a delicious vegan restaurant nearby - Veguísima! We only stayed a few nights, so we mainly just explored the Bosque de Chapultepec nearby - including the seemingly out-of-place but magnificent Chapultepec Castle, and the incredibly relaxing and highly recommended Audiorama.

Then we went to pick up our rental car for our trip down near the “Laguna de Tequesquitengo,” where we booked a very long stay at a very low price simply to get our budget back in order.

However, car rentals in Mexico are very different than most other countries and it caught us by surprise. Here’s something to caution you about the Mexico City airport, Europcar specifically - but likely every rental car company in Mexico. We've traveled in many countries - 46 in total. Some have no issues with accepting the rental-car insurance provided by credit cards. Some, require a bank note. Others require a gigantic hold on the card (upwards of €5,000). We don't complain about any of that. Plus, we've even used Europcar in a number of other countries. This one was different. A 2 day rental was a little over $165. Ugh, fine, but then they won't accept credit card coverage for the car at all. Must pay $234 for their insurance. Wow. Two days rental for $399! No thank you. A full 2 hours completely wasted. So we ordered a 2 hour Uber XL to get to our next destination instead, for $186.90 total. Just know that you’ll have to pay for the car insurance in Mexico - there’s no way around it!

But, check this out: 3 bedroom, 3 bathroom place, full kitchen, backyard, AC, laundry machines, stove/oven, desk to work, pool, and a Waterpark on the property all included. All utilities included. For $634 per month. We were in a fairly beautiful area, south of Cuernavaca.

This really helped us get caught up on work, relaxation, and even help recover our budget. We ate a lot of tacos. And a lot of burritos. Plus plenty of “pan de muerto,” a local bread with orange zest and sugar coating - and Mexican hot chocolate, which is infused with cinnamon, chili, and semi-sweet chocolate.

The kids loved playing at the water park. We hired a local man to drive us around, and visited a few really amazing places - our favorite was the Jardines de México because the food at their Dalia restaurant was absolutely divine!

Occasionally, during the night, Toshi wouldn’t want to go to bed. Instead, he decided to stay up in the dark and go hide a few of his animal toys. Then, he would ask daddy to come on a safari with him using his phone flashlight. Bradley walked around the house with him looking for his animal toys - replicating his night safari experience in the Monteverde Cloud Forest of Costa Rica. It was so sweet and cute that we couldn’t say no to him. What a memory! This is the traveling lifestyle.

Deciding to Immigrate to New Zealand

While enjoying our relaxing lives in Mexico, we began reminicing about our favorite places around the world. Of course, New Zealand was at the top of our list - along with Hawaii, Cape Town, Malaysia, Switzerland, Türkiye, and Scotland. After a bit of research, we decided that New Zealand was the best place for us to raise a family. So, we paid for an initial assessment at New Zealand Shores Immigration Service to see if there was any way that we could make it a reality - knowing that the Working Holiday Visa wasn’t available to people over the age of 30-35 years old.

“I am happy to tell you that based on the information you initially supplied you may be eligible to move to New Zealand under the following categories:

1. The Accredited Employer Work Visa Category

2. The Skilled Migrant Residence Category”

While looking into these categories, we learned about New Zealand’s “Green List” - one that is a fast-track into residency for people with skills that New Zealand is short on, particularly just about everything in the medical field, electricians and plumbers, early childhood (pre-primary school) teachers, and just about everything involved with programming, software development, and ICT (IT).

So, we looked into these fields as well and - during that process - ended up realizing how easy it was for anyone to have the type of lifestyle that we've been enjoying over the last 5 years.

Before we started traveling we searched high and low for “nomad” or “remote” jobs, but the only ones that were available were programming and developer jobs, so - with no time to get a computer science degree - we dismissed them. But, since 2020, training to become a programmer has become far easier and far quicker than it used to be. Now it can be done in as little as 2-6 months, and for as little as $499. So, as those types of remote jobs start out around $70,000 and are in high demand - especially in New Zealand - Jenny decided to start learning how to be a full-stack developer using the Remote Coding Remote Coding Bootcamp. This was likely Jenny’s best chance for landing a visa, and a great back-up for remote-work if it didn’t pan out.

In fact, that back-up plan was so solid that we realized it was the easiest path for anyone to be able to travel the world endlessly. So, we wrote an article detailing exactly how to do that:

• Retire Early: Have the Life that You Want to Have Now and Get Rich Faster

Bradley’s best option was the Accredited Employer Work Visa and Skilled Migrant Residency pathway as he has an MBA in finance and there were a number of available jobs in accounting and finance. However, most New Zealand jobs in this area require a CA qualification, similar to a Certified Public Accountant (CPA) qualification in most other countries, but some prefer a strong focus on financial modeling and analysis and possibly the Chartered Financial Analyst (CFA) designation. These designations take a while to get, but Bradley could quickly build up his financial modeling skills with training through the Corporate Finance Institute, which turned out to be quite impressive and reasonably priced. It’s good to note that remote CPA jobs are also in demand, higher paying than remote bookkeeping jobs, so this isn’t a bad path either!

With the potential in hand and our ability to make it a reality, we decided to pay for the immigration service and begin preparing the mountain of paperwork. Resumes/CV’s, passport photos, birth certificates, passports, federal background checks, getting our degrees verified through the NZQA system, attaining and providing verifiable work experience, providing a ton of relationship evidence (including tenancy agreements, marriage certificate, relationship support letters, photos, etc), and health exams - are all required in addition to accepting a job offer. So, we spent weeks putting together what we could and then arranging appointments to do the rest.

In the meantime, our sense of “it’s actually going to happen” got the better of us and we ended up watching all of the Lord of the Rings films, the Hobbit movies, the new Rings of Power show that came out while we were doing this process, and a ton of YouTube videos about living and traveling around New Zealand. We felt like we were living in New Zealand while we were living in Mexico.

It was crazy, and our emotions were all over the place on whether this transition from the Remote Life to the Expat Life was actually going to happen, what major roadblocks could prevent it, and what we would do if it actually happened.

Either way, our travels were set to continue at least until February of 2023 - when our flights were booked - work visa or not.

A Quick Trip back to Orlando and the Theme Parks

As we were trying to get all of our paperwork together, we realized that if things worked out in New Zealand, we likely wouldn’t be making many trips back to the United States in the next 5-7 years. So, we did end up deciding to make a quick trip back into Florida - mid-November - to visit Jenny’s parents and her sister’s family before we departed. They were kind enough to cover our travel expenses for this trip, to which we are very thankful!

We also were able to get the kids their first dose of the Covid vaccine while we were there, as well as our second boosters, even though Florida didn’t make that easy. At this point, much of the world had already stopped caring about the Covid pandemic. However, children under 5 years old had only recently been approved for their first doses - meaning that families with young children really were last to be protected and - with the common cold, the flu, RSV, and covid all being “accepted” these days - we didn’t want an endless cycle of our kids constantly getting sick throughout the years (no thanks!).

Jenny’s family greeted us by inviting us out to the Walt Disney World parks. They brought us to Hollywood Studios, Animal Kingdom, Magic Kingdom, and then to EPCOT - all in a single week! The kids loved meeting Mickey and Minnie Mouse and we really enjoyed the Star Wars: Rise of the Resistance ride in Hollywood Studio’s new Galaxy's Edge area. We also all enjoyed the safari ride at Animal Kingdom, even though it felt more rushed than it used to be.

Bradley met up with his friend Jon at Universal Studios as well. They both enjoyed a few favorites, drank a butter beer in the Harry Potter area, and tried out the new “VelociCoaster” ride at Islands of Adventure. Jon is a friend of his from college who went the Computer Science route and has been an IT Project Manager and DevOps Engineer - with experience as a programmer going back to 2010 - so, they had plenty to talk about concerning the best career paths and tools for people who are looking for remote programming jobs in todays marketplace.

Even though we visited the theme parks this time, we usually like to go the more affordable route and visit natural Florida instead. Here are a few of our favorite nature places to visit around Orlando:

• The Best Natural Places in Central Florida: Nature Parks, Gardens, and Springs - USA

Alone in the Florida Keys and 3 Celebrations

After that, we decided to take a couples trip down to Key West, Florida - without the kids. Bradley’s mother came down to help Jenny's parents watch them while we were gone. We’ve never really had a break for ourselves since the kids were born, and with Ellie just about to turn 2 and Toshi a few months away from 4, we really needed to have some time together as a couple.

On our way down to Key West we stopped in Miami to take care of our background check requirements for the New Zealand immigration paperwork, then we spent three nights relaxing in the upper keys and kayaking a bit.

A day trip down to Key West’s historical area, with a local tour by Bradley’s Uncle Ken, made it a very memorable experience. There’s much more history to the Florida Key’s than we realized, and we certainly enjoyed the food there as well - especially the amazing fresh Fish Rolls at What The Fish Rolls.

After heading back up, we noticed that Toshi had become sick and was acting far different than usual, so we brought him to an Urgent Care on November 22nd - 2 days before Thanksgiving. For $367.75, they determined that he had a fairly developed ear infection and prescribed him with amoxicillin for 7 days, 2 times per day ($8.05 at Target). We felt really bad that we weren’t there for Toshi when he got sick, and it ended up being quite hard on us over the next few weeks while he recovered because he wouldn’t communicate at all, shut down regularly, and screamed uncontrollably about anything that wasn’t perfect. We didn’t know what to do but be there for him, even though it was nerve wrecking for us!

He definitely wasn’t recovered by Thanksgiving, but we still managed to have a decent meal with the family, a full month early Christmas party for the kids, and a really nice 2nd birthday party for Ellie a few days afterwards - all somehow their own separate things! Toshi’s recovery was up and down during that time.

Then we headed back to Mexico City for a few more weeks.

Día de los Muertos (Day of the Dead) and Teotihuacán

Actually, just before we went to Orlando to visit friends and family, we took a few nights in Mexico City because they were having Día de los Muertos celebrations at the time. This is one of Mexico’s most important religious holidays, so we wanted to learn a bit more about it than just what we learned in Disney’s Coco movie - although that movie does a very good job!

It is a multi-day holiday where Mexican families joyfully celebrate and remember their friends and family members who have died. This holiday has become a bit more mainstream in the United States, and other parts of the world, over the last 10-20 years as well. Actually, there were no Día de los Muertos parades - even in Mexico - until after filmmakers created one for the James Bond film Spectre. That one was simply put together for the movie, but the first official parade was put together in Mexico City in 2016, the year following that film’s release. In other words, Hollywood influenced a change in how Día de los Muertos is celebrated. The Mexican people that we talked to about this seemed mostly positive about the parade, saying that it would generate more awareness of the holiday.

While it’s not typical for us to go out at night with the little kiddos, we did it every night for Día de los Muertos. The kids mostly behaved after it got dark, and we managed to see many calaveras (iconic painted skulls) and alebrijes (colorful spirit guides created by mixing two or more animals together) as we walked down the Avenida Paseo de la Reforma trying various street snacks along the way. There was also a huge night candle event at Bosque de Chapultepec, but the line was so long at night time that we could only go during the day. Massive ofrendas were seen in the Plaza de la Constitución, as well as a number of people dressed up for the event throughout this square and all down the streets leading between there and the Palacio de Bellas Artes. Not far from there, in Garibaldi Square, mariachis dressed in traditional attire could be heard playing traditional music on trumpets, violins, the vihuela (a guitar/lute), and especially the guitarrón (bass guitar). It was quite an experience!

After returning to Mexico City from Orlando, we had intended to go see the Magical Xochimilco Trajineras - which were still doing Día de los Muertos boat rides down canals, offering up tequila, and playing mariachi music. Instead, we spent a few weeks tending to Toshi as he was still quite sick from his ear infection after we arrived and was acting very strange and very difficult. He would scream bloody murder and needed to be held down to get him to take his medication. We were honestly on the brink of losing our minds - we felt so bad! But, he did end up recovering after about 7-10 days, and then immediately ended up catching a stomach bug after that. It really was no fun at all.

We were lucky enough to get a single day trip out to Teotihuacàn at the end of that three week period, where we saw the Templo de Quetzalcóatl, the Pyramids of the Sun and Moon, and even got to eat at a magical cave restaurant called La Gruta (even though we didn’t care much for the food there).

We’ll have an article about all of the places that we loved around the Mexico City and Cuernavaca areas soon.

Visiting Family and Friends in Chicagoland over Christmas

Our friends convinced us that Chicagoland was getting a bit warmer than it has been in the past, so they recommended that we visit. As Bradley has a number of friends and family in this area, we decided to stop out there for 5 1/2 weeks - mainly because Andrew and Kathy offered to host us and let us drive their Tesla Model S while we were there (that was incredibly generous and unexplainably helpful for being able to stay in the U.S.).

On our first full day in Chicagoland, we took the kids in for their second dose of the Covid vaccine (2 out 2). The next few days entailed us getting to hang out separately with a few of our friends - Bradley hung out with Andrew and Steve while Jenny hung out with Kathy and Elizabeth - something we haven’t been able to do since starting our travels early in 2018. We both definitely needed that!

Then, we were slammed by a typical Chicago cold front and the temperatures dropped to -23 to -20 degrees Celsius (-9 to -4 Fahrenheit), with a windspeed of 35 km/h (22 mph) - gusts making it feel as cold as -48 degrees Celsius (-24 F)! When heading out to see the new movie Pandora: The Way of Water with our friends, the wind hurt our faces so bad immediately after getting out of the car that we had to turn around and walk backwards from the car to the theater doors. The inside of Jenny’s nose froze. Bradley got inside and stated, “Yeah, this is exactly how I remember the weather in Chicago!” So cold. So bloody cold! Ok, most of the time that we were there it was slightly warmer than normal, but that week it was rough as neither of us likes cold weather!

Over the next few weeks we spent quite a bit of time visiting family and friends for Christmas and New Years events. Three different Christmas parties for various parts of Bradley’s family - his parents, his grandmother’s, and his stepfather’s extended family - a quick stop by one of his mother’s cousin’s house (Mary Ellen), and a couple evenings at his friend Chris’s house.

Bradley's mother then put together a family trip up to the Wisconsin Dells, for his niece’s 21st birthday. Shelby - his niece - and his brothers Brandon, Taz, and Nick (and Maddie) - all enjoyed playing with the kids at The Great Wolf Lodge waterparks. If you've never been to the Wisconsin Dell’s, they are definitely worth checking out.

Afterwards, Bradley made a few solo trips to see his friends Steve and Ryan. We managed to explore Bradley’s hometown a bit, try the infamous “Country Donuts,” as well as some vegan versions of Chicago style hot dogs, roast beef sandwiches, and deep dish pizza.

We go in detail about our favorite places in Chicagoland - with a few hidden gems that we saw on this trip - in this article:

• Explore the Best of Chicagoland: Must-See Attractions, Landmarks, and Hidden Gems

It was really great to meet, and catch up, with so many people during our visit to Chicagoland, as well as trying all the amazing food, but we were happy to move onward towards a warmer place.

Visiting Family and Friends in L.A. California

Our affordable ticket to New Zealand actually was set to depart from Honolulu, Hawaii, so we still had to make our way over to Oahu. However, we also made it a point to stop in Los Angeles for a week before heading out there - to visit Jenny’s extended family, and her many friends, living in or near the city.

Her Auntie Nobie and Uncle David graciously hosted us for the week and even let us borrow one of their cars as well. Nearby, in Rancho Palos Verdes, the kids loved walking to a fun playground and park. This area has wonderful views of the ocean as well.

On one of our days in LA we headed out for a meal at the King’s Hawaiian Bakery & Restaurant - which has some amazing Hawaiian food as well as a very relaxing atmosphere - with Joyce and Uno, friends of Jenny’s that we had last seen when they were living in Singapore and Toshi was about six months old. It was great to catch up with them – and see Toshi and Uno chat and play like old friends.

We also went to the Lunar New Year event at South Coast Botanical Garden to meet up with some friends that Jenny had met while teaching English out in Japan - and that were now living in LA - Jen and Hiro (and their son, HanWool), and Zelda, Taro, Justin, and Emily. Her cousin, Daryl, her Uncle Dan, and her college roommate, Hyejin (and her son, Nate) all also showed up. South Coast Botanical Garden has a Banyan Grove with fig trees, a Japanese Garden and Koi Pond, a Mediterranean Garden, and a Rose Garden among other sights and paths to wander and relax. Toshi had a great time playing with Cousin Daryl as we explored the gardens. It was a beautiful day to hang out and fun to introduce our growing families to each other during the Lunar New Year event.

On a separate day, we had lunch over at her cousin Heather’s house in the Redondo Beach area. While there, we got to talk with her husband, Tony, her cousin Michelle (and Michelle's husband Jimmy), and a bit more with Uncle Dan. Bradley had a good business conversation with Tony, and our kids loved playing with their kids. Toshi and Ellie even got to try riding a scooter for the first time at a nearby park.

Later that evening, Jenny’s Uncle Ron and Auntie Nancy invited us to a family-style Italian dinner at Il Fornaio Manhattan Beach, which is a very elegant feeling restaurant with menu offerings from various regions of Italy. A number of her other cousins were there and it made for a large family gathering. We all did our best to learn more about each others lives while enjoying bites and juggling the kids around the table.

Although we didn’t get to meet up with everyone during our visit, we think we did well. Plus, there are so many great places to see and explore in LA that a single week is hardly enough to see everything, especially when focused on meeting up with friends and family.

Sadly, we couldn’t stay longer as we had to get to Hawaii in time for our flight to New Zealand – and we couldn’t pass up the opportunity to show our kids around our favorite old stomping grounds!

Feeling at Home in Hawaii

We arrived home on February 1st. At least it felt like arriving at home! Full disclosure: Hawaii is very expensive especially accommodations-wise and we wouldn’t have been able to afford it without being hosted by friends or family. We had a number of people offer us to stay with them, but one by one things came up that didn't make it possible or they were still being very cautious about Covid. Thankfully we were able to find a place to stay a few weeks before our arrival. Huge shoutout and thank you to the McWilliams family!

Jenny had grown up in Hawaii, and Bradley lived there for a couple of years as an adult, but we had never been there together. So we each had places that the other person hadn’t seen before – plus both of our kids had never yet been to the islands.

We started off our Hawaii adventure with a day in Ko’olina, on the westside of Oahu, and took the kids on a walk along the lagoons. They loved playing in the water and digging in the sand. We also made our way over to Aulani for lunch and were able to get a few high-fives from Goofy, Max, and Chip and Dale. The kids loved getting to do that!

We visited the church Jenny grew up at, and ran into some family friends – Uncle Wayne and Auntie Patty. They invited us to a picnic with their friends at Magic Island - one of which happened to be visiting them from New Zealand! So we got to chat with her about her immigration story and how it has been for her after living there for many years.

Even though Hawaii is an island with many beautiful beaches, salt-water pools are also popular – especially if you have kids, which we do now! Lisa - Jenny’s best friend – invited us over to her place over by Ward for the day, and it was a great setup with the kids being able to splash in a shallow pool with a playground also nearby. Jayme – another of Jenny’s friends – also invited us over to the pool by her place in Pearl City and our kids got to play with her kids a bit.

Our sightseeing was not over though! We also visited Ho’omaluhia gardens, Byodo-in temple, did the Lanikai pillbox hike, and drove up to the North Shore and explored Haleiwa. The kids had their first shave ice at Aoki’s and loved it. Neither of us had ever done a tour at Kualoa Ranch, but it’s such a major tourist hotspot that we decided to book our first tour there – the Hollywood Movie Sites Tour – and got to see breathtaking scenery as seen in films like Jurassic Park, 50 first dates, Kong, Windtalkers, and many more. A definite must-do for movie fans, and really for anyone as the landscape is so gorgeous that just getting to see the valley is worth the price alone.

Two days before our flight out we brought the kids to Honolulu Zoo for Toshi’s 4th birthday party. They loved seeing all of the animals, but their highlights ended up being the playground and the petting zoo! The day before our flight we were lucky enough to meet up with Jenny’s relatives Chieko and Jeff, who brought us out to a local Island Grill. It was good to finally meet them in person as they seem to read about all of our travels!

After 10 full days of adventure, sightseeing, and eating our way around Oahu, it was time to say Aloha to Hawaii and Kia Ora to New Zealand.

Flying into Auckland during the Cyclone

As weird as it is, our flight left Hawaii early morning on February 11th but didn’t arrive in Auckland until February 13th - due to flying over the international date line. We technically only experienced a few hours of February 12th during our short and rushed layover in Sydney, and thus why we celebrated Toshi’s 4th birthday a few days earlier in Hawaii. Additionally, tropical Cyclone Gabrielle was set to hit Auckland on February 12th. Here’s the story:

As we were departing Honolulu, the person checking in our bags was in training and short tagged them into Sydney. We caught the mistake, but the person insisted that we had to pick them up in Sydney and re-check them to Auckland. In a very rare moment for us, as we were tired and already exhausted with all of our luggage and the kids, we accepted that he knew what he was doing. When we arrived in Sydney we attempted to go claim and re-check our bags (the luggage stickers had the Sydney code on them). However, without visas to enter Australia, the customs agents did not allow us to cross into the bag claim area despite explaining our case. They insisted that our bags should go all the way through to Auckland, and - under normal circumstances - we would agree.

We went to the boarding gate for our flight to Auckland and explained the situation again to the flight crew. They checked and agreed that our bags were short tagged to Sydney, not all the way to Auckland, but that they would correct it and get the bags on the flight to Auckland with us. We had a moment to check the board. Some of the earlier flights out to Auckland had already been canceled due to the first parts of the cyclone reaching the city. We began to wonder if we’d be staying in Sydney after all. Then, some flights after ours started getting canceled. We were all but certain that ours would be as well.

Surprisingly, our flight crew got on the intercom and began boarding everybody all at once. We looked at each other like “WTF?!?” - but, they just kept boarding. Bradley asked a crew member if it was safe to go, considering the cyclone, and the crew member stated that the pilot believes it is safe as there appears to be a gap in the storm that’s long enough to allow them to land if we depart now. So, we all hesitantly boarded the flight into the cyclone. Despite some fairly bumpy turbulence on arrival into Auckland, we did land safely around 1:00 AM, and were pretty surprised that we made it.

What didn’t make it was our bags. We could tell because we were tracking them with Apple AirTags and could see that they were still in the international section of the Sydney airport. The lost luggage personnel in Auckland informed us that it may take up to 3 days for that luggage to arrive and that they would deliver them to us when they came in. Thus, we also didn’t have car seats for the kids.

Grabbing a free trolly at the airport, we rolled ourselves through the wind to the Ibis hotel 1.2 km away (just under 1 mile) and fell asleep. A few hours later, the rain coming down from the cyclone, we took turns hurrying across the street to buy car seats for the kids and then made our way out to our Airbnb in Coatesville (near the DotCom Mansion) shortly after checkout time. The cyclone had knocked out the power at our Airbnb, and our water - as it runs on an electric pump. No cellular signal. No internet. For two days we collected rainwater as the cyclone blasted through, enough to keep refilling the toilet tank. Valentines Day stuck at home. The next day we signed up for a gym membership to take advantage of their showers. Roadways were washed away, other areas severely devastated. We were lucky.

On the 16th, our power came back on and our bags arrived at Auckland Airport, but we only knew due to our Apple AirTags. We tried updating Jetstar in their lost luggage system online, and even talked to a person at their call center, but they all seemed to think the bags were still in Sydney. Still hearing nothing from Jetstar by February 18th, we made our way to the Auckland Airport International Baggage Services building and waited for about two hours to gain entry and recover our bags. Our stroller was delivered to our Airbnb about a week later. A few months later, Jetstar found our car seat in Sydney - we told them to donate it to the Salvation Army.

On March 20th, we finally reached a settlement with Jetstar about a claim on our lost luggage regarding the purchase of necessary items that were required due to the baggage delay, in the amount of AUD $1,359.39. Despite our need to buy many new things, this ended up making our total flight cost to New Zealand for 4 people about USD $478. Not too shabby, but what a crazy experience!

Exploring New Zealand while Open to Job Opportunities

We’d been to Auckland before, but we definitely wanted to explore a few more places. In our attempts to go to Piha Beach and the Waitakere Ranges, we were directed back due to the roadway being unsafe - mostly washed away - and the town there being one of many on the north island that were devastated by the cyclone. We walked the forested paths of the Eskdale Reserve instead.

A few days later, Bradley took a trip out to Auckland to meet up with a recruiter for KPMG, but the job they were looking to fill wasn’t a match for him.

As we were staying in Coatesville, we also went to the local farmers market - common across New Zealand on Sundays at least once or twice per month - and we had a great time trying some local food and fresh pressed juices. Next, we made our way out to the Auckland Zoo so that the kids could see a live Kiwi bird run around. As it was quite dark in the kiwi room, the only one they could see was the one that was sleeping in an open area.

We had visited Wētā Workshop in Wellington the last time we were in New Zealand, and loved it, but we had just learned about Wētā Workshop Unleashed in Auckland - so, we brought the kids and had a creative movie-workshop experience with them. They were brave enough even for the scary parts - and we were happy to see some more amazing Lord of the Rings memorabilia and mock-ups at the store area. Just next door was the Sky Tower - amazing to see up close!

Bradley talked to another recruiter via Microsoft Teams about a job they needed to fill at Heartland Fruit in Nelson. We even started buying, and eating, many of their Luv’ya branded Eve apples for a week or so. As it turned out, it also wasn’t a match.

Our last little adventure in the Auckland area this time around started with a quick stop at Mount Eden on our way out to Auckland Botanic Gardens. Toshi loved running up the stairs at Mount Eden, and we loved the views of the city, but the kids got a bit chilly from the wind and wanted to continue onward. Our favorite spots at the Botanic Gardens were the Potter Children’s Garden, the Perennials, the Subtropical Oasis, and the Rose Garden - all very picturesque and certainly worth a visit, especially with kids!

Moving to Hobbiton and a Quick Trip to Wellington

Next stop was Matamata, the town more popularly known as Hobbiton from the Lord of the Rings and Hobbit films. The movie set for Hobbiton was built there and is still fully viewable by booking a tour. Having been to the movie set ourselves, when Toshi was just 1 year old, we weren’t in a rush to go again. Instead, we strolled around the town of Matamata a bit, stopping by some restaurants and ice cream shops - as well as the Hobbit House themed visitors center there.

Many of our nights here were clear dark skies with amazing views of thousands of stars - the milky way clearly visible with the naked eye. That is not a sight that we normally get to see anywhere near a city or town anymore and we spent many moments over the next few weeks simply looking up in wonder late at night.

One day, we took a trip east of the town to trek up to Wairere Falls. Wow, what an amazing hike that was - we completely recommend it for those of you who don’t mind a slight incline or a few stairways! Gorgeous walk along a rolling stream, amazing forest canopy with lichen covered rocks and green mossy trees, plus an incredible view of the waterfall!

Shortly thereafter, a recruiter called Bradley recommending a possible match with a private kiwi-owned company. We had never heard about the company before, but decided to look into it and became rather interested. The company wanted to meet Bradley in person, so he drove down to Wellington to meet them - a normal 6 1/2 hour drive that was doubled due to our silly decision to rent an early generation Nissan Leaf with low range. However, the meeting went well, and so did the interview that occurred a few days later. So Bradley rewarded himself with a delicious New Zealand pavlova at the Dockside Restaurant & Bar nearby.

As we were nearing the end of our 5th year of travel, Bradley decided to drive back up to Matamata to celebrate with us as a family. On his way, he stopped at the US Marines Memorial at Queen Elizabeth Park - as he served from 2001 to 2005 and wanted to see what this memorial was about. He spent the rest of his day, through the night, making his way back home.

The day after he arrived, we celebrated our 5 years of adventure by taking one more tour of the Hobbiton Movie Set. It's really an amazing place!

Awaiting the Decision - New Zealand or Onward

It is hard to be in limbo, not knowing if Bradley will get a job offer in time - before we have to leave New Zealand. And, even if he does, will our visas be approved to work in New Zealand? It may be the end of March, but as we were required to have a flight out of New Zealand prior to entering the country, our tickets out are already purchased - a flight from Auckland to Sydney on April 29th. That gives us just one more month to see what happens.

If things work out, we may be basing ourselves in the Wellington area for a few years while traveling in this region of the world - albeit a bit less frequently than normal - until the kids get a bit older and easier to manage.

Provided that Bradley does not receive a job offer, or that our visas are not approved, our plan is to continue on past Sydney back towards Nusajaya, Malaysia - another place that feels like home to us and is very affordable. There, Bradley would take the back seat and bring the kids to Legoland and SeaLife Aquarium on a regular basis while Jenny focuses on remote programming work. After another 3 months in Malaysia, we’ll likely head up to South Korea or Japan so that Bradley can teach English there - and possibly meet up with an old friend. Oh, yeah, we forgot to mention that Bradley also completed his TEFL certificate while we were in Mexico, so he’s qualified to Teach English as a Foreign Language as well!

What a crazy adventure it has been this year! Let us know your questions in the comments section at the bottom of this article - we’ll be sure to respond within a couple of days!

UPDATE: As of May 25th, 2023, Bradley received an Accredited Employer Work Visa, allowing us to stay in New Zealand for the next 3 years.

The Growth of Our Blog

1. Our Challenges

Our main challenges this year were trying to get our budget back in order and finding places to stay while traveling across the United States. We’ve been learning more about taking on remote programming jobs, as well as what it takes to get a work visa in New Zealand. Our expenses haven’t really gone down with the kids getting a bit older, and we feel it’s necessary to find more ways to bring in money. Luckily, family and friends pulled together and helped provide us with places to stay while we visited Florida, Chicago, LA, and Hawaii.

2. Our Goals & Achievements

Our goals this past year were to improve the OGCS service, catch up on our travel blogs, improve traffic to our website using SEO and videos, and improve affiliate income.

We mostly caught up on our unfinished travel blogs, but then fell behind again afterwards. However, years 1, 3, and 4 are complete - with only 4 articles left from year 2. Year 5 now has another 5 articles to go, as well as a few updates on previous articles. That’s 9 more articles until we’re all caught up! As for improving our blog traffic using SEO and videos, we’ve been doing a fair job at improving the SEO and SEO in images on our site - however, there’s still a ton to do and we still haven’t managed to get around to many videos. No, we haven’t been focused on affiliate income this year, and we’ve actually discontinued the OGCS service as memberships have decreased over the year. Instead, we’ve started up the Remote Coding Bootcamp, which has pulled in a few students already. We’re set to start ramping that up to make it even better in the next few months!

3. Website Traffic

Over the last year we’ve accumulated 46,112 more page views (+77% yr/yr) and 33,942 more visits (+61% yr/yr). So, our totals are now 181,195 total page views and 133,385 total visits. We are currently receiving about 4,359 page views per month, which is up about 73% from last year. We believe we will likely have 2-3 times that next year.

4. Marketing Strategies

Our current marketing strategies consist of standard SEO and image SEO, as well as sharing posts in Facebook groups. Our plan is to work more on SEO this upcoming year, putting proper image SEO tags in older articles, and potentially adding videos to our articles. We are hoping that AI technology will be helpful in regard to these tasks.

5. Revenue

Revenue jumped from $2,518.93 last year to $4,600 this year, an increase of 82.6%. We are hoping to reach at least $12,500 in year 6.

If you have any advice for us, please feel free to share it!

Learn more about our fourth year of traveling as parents, the highlights of year 5 of traveling the world, and some of our mishaps below!

The Fourth Year of Parenthood while Traveling the World

It is not easy to travel full-time with two toddlers. It’s a little easier when they are not walking yet, but it’s still not easy. Our work schedule changed a bit – Jenny working 6 hours in the morning, and then Bradley working 6 hours in the afternoon/evening with our days starting early and ending late. I’m not sure many parents get quality sleep – we sure don’t.

Now that our son is 4, he has been very interested in turning 5 and going to school. He is very active and is just starting to get more adventurous at trying new foods again. He still loves playing in the water and took every chance he could to go swimming while we were in Hawaii. He is very interested in numbers and had many friends and family helping him count to 100 multiple times until he could do it on his own the week we were in LA.

He has learned to spell his name – so he now calls himself Toshi instead of “Oshi.” He is very caring and kind and looks after his sister most of the time.

Ellie is still an adventurous explorer. When she’s not busy climbing up windows, she’s asking to go outside and go hiking. She’s become a little more cautious going down slides – she had an unfortunate experience going down a tube slide while bigger kids were climbing up, so she’s a bit more hesitant on those now.

Learning people’s names seems to be important to her. She’ll repeat them until she remembers and then she’ll mention their name months later. She is a foodie – preferring brie to string cheese, muesli instead of froot loops, and sourdough egg and gouda cheese sandwiches rather than pb&j.

She is still loud and demanding, but she’s getting better at saying please and thank you. She’s very good at sharing and loves to be the one to hand Toshi his share of snacks.

Our kids fight as siblings tend to do, but they also love each other a lot. If one is crying, the other one will go run and check on them and sometimes they will even sing to each other to help them calm down. It’s very sweet to witness.

Highlights from our 5th year of travel

HIGHLIGHTS OF THE YEAR

• Exploring 1 new country as a family, 2 new countries for Toshi, and 3 for Ellie.

• Having “Grandma Betty” join us in Costa Rica for a week of adventures and her birthday.

• Having a free waterpark in the neighborhood of our rental in Mexico.

• Eating an amazing meal that included freshly picked veggies from the garden at Jardins de Mexico.

• Taking the kids to WDW for their first time and seeing the magic come alive for them.

• Getting to relax in the Florida Keys as a couple.

• Learning that immigrating to New Zealand was a real possibility even if it was going to be a lot of work.

• Being able to spend time and introduce our kids to family and friends in Chicago, Los Angeles, and on Oahu.

• Spending time at “home” exploring Oahu and showing the kids our favorite spots – Aulani, Ko’olina, the Honolulu Zoo, Lanikai Beach.

• Eating REAL poke, shave ice, lau lau, lomi salmon, and poi in Hawaii.

• Seeing the gorgeous landscape at Kualoa Ranch.

• Landing safely in Auckland in the midst of Cyclone Gabrielle.

• Having air-tags in our luggage made it easier to get them back.

• Viewing the milky way and so many stars at night in Matamata (Hobbiton).

• Getting a car “subscription” for a month for the price of about a 4-day car rental.

This past year we did get to explore a bit, but many of the highlights include the time we were able to spend with our family and friends. It was so nice to be able to catch up in person – which has been difficult for us to do while traveling full-time but doubly so due to the pandemic regulations the past few years.

2022-2023 was a slower travel year for us. We visited new places and cities but less countries. We tried to stay in places for longer periods of time to catch up on work and study. We sought out playgrounds and wide open spaces for our toddlers between botanical gardens, museums, and other adventures.

We are very thankful to live this life and love sharing with and teaching others who are interested in a similar lifestyle.

Check out our budget and learn how we can afford to travel endlessly on our other pages.

Mishaps & Lessons Learned in our 5th year of Travel

We’re not perfect, and we've had our share in this 5th year of traveling full-time of a few mishaps and learning experiences.

Over budget: We had been doing really well on our budget of $2000/month. Until we bought plane tickets back to the US in January of 2022. We spent most of this year trying to make up the difference by staying in really affordable places. But that led to….

Low-budget housing: We stayed in a place with gorgeous views of the mountains in Colombia. But it unfortunately had many bugs. Bradley was able to eradicate many of them during the month that we were there, but we were always looking forward to moving out. The next place was rated 5-stars on Airbnb and the reviews were very favorable. However, when we arrived, the host told us to not go outside at night and don’t take our cell phones out of our pockets or bag even during the day. That evening, we also realized the place was infested with bugs all over the kitchen and coming out of door jams. We needed to move and found a place double the price, but it was clean and in a safe neighborhood. If you go to Medellin, stay in Envigado!

Car rentals: Mexico may be affordable to live, but car rentals (at least in Mexico City) are very expensive. We wrote about it in detail above, but a 2-day car rental would have been 2/3 the cost of a 1-month stay at a 3 bedroom, 3 bathroom place!

Health: We usually stay relatively healthy – and with the past few years of social distancing it’s been easy to keep the kids healthy as well. But this year we tried out a daycare and the whole family was sick for two weeks, and then Toshi got his first ear infection while we were in Florida visiting family. It’s really tough to see your kids sick and congested – they’re so small and usually full of energy.

Lost luggage: As seasoned travelers we did catch that our luggage was short-tagged to Sydney instead of all the way to Auckland. But when the gate agent insisted we would have to pick up our bags and re-check them during our layover we didn’t question it further. If we had taken the time to do so, our bags might not have been delayed. But thankfully we had the Airtags in the bags and in the stroller!

Short-range car: We discovered that New Zealand has “car subscriptions” here that make renting cars for a month or longer much more affordable. Having owned and borrowed various EV cars and hybrids, we chose a Nissan leaf since it also came with unlimited kms. While it has saved us money – it’s about $400 usd/month – it also only has about a 110 km range. So it makes driving long distances very time consuming with the charging.

Cell service and WiFi: When we landed in Auckland, Cyclone Gabrielle had knocked out the power and water. So our place had no WiFi to do things like order an uber to get to the store or even send a message to our hosts. Bradley had picked up a sim card in the airport when we landed, but our place was in a rural area with no cell service. Later in Matamata, when Bradley drove down to Wellington for some interviews, the WiFi data ran out at the house. Jenny didn’t have a cell plan because usually we’re always together to share one plan. So it took a couple of days before more data was added and we could contact each other.

Mental burnout: We’ve learned in past years that moving too often is mentally taxing. This year we tried not to move as often, but we did add in a few trips throughout the year to get things like background checks done in case our dreams of moving to New Zealand panned out. We also had a few emotional ups and downs as things go when you’re job searching and things don’t work out.

Each year of travel brings its own challenges and lessons learned and hopefully you can learn from our mistakes!

Thank you VERY much for reading our article. We actually created this website to help people reach financial independence. Did you know that by having a remote job and traveling endlessly, or living in a country that has low costs of living, you can actually reach retirement quicker? Plus, retirement abroad is up to 75 percent cheaper as well! Learn more by exploring our website: EatWanderExplore and REmotiFIRE.

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