One of the biggest challenges of planning a move is figuring out where to go.
Over the past 9 months, we’ve spent countless hours researching different destinations, comparing costs, reading expat experiences, and imagining what daily life might look like in each place.
After months of research, three locations have consistently risen to the top of our list:
- Florida
- Puerto Rico
- Thailand
Each offers something different, and each comes with its own challenges.
Here’s how they compare based on the factors that matter most to us.
What We’re Looking For
Before comparing locations, it’s important to define what you’re actually trying to achieve.
Our priorities include:
- Warm weather year-round
- Affordable cost of living
- Access to beaches and nature
- Reliable infrastructure
- Good healthcare options
- Safety
- A slower pace of life
- Quality of food
No place is perfect, so the goal isn’t to find perfection—it’s to find the best overall fit.
Here’s how each destination measures up against the priorities that matter most to us.
Florida
Pros
- Familiar financial systems
- Easy access to products and services
- No international relocation costs
- Warm weather year-round
- Access to beaches and nature
- Reliable infrastructure
- Quality of healthcare
- No visa required
Cons
- Housing costs are very high
- Healthcare and homeowners/renters insurance costs continue to rise
- General cost of living has increased significantly
- Safety is a worry for us with the amount of shootings and violence in a big portion of America
- Our pace of life would probably increase in Florida compared to where we currently are in the midwest
- Concerns about the prevalence of highly processed foods and ingredients commonly used in the U.S. food system
Verdict
Florida is the most expensive option of the three which made it significantly less appealing. It’s difficult to justify spending such a large portion of our income on housing alone. Aside from expenses, safety in America has been a concern for a while and pace of life would be the same, possibly even increased from our current location.
Puerto Rico
Pros
- Generally lower housing costs than many parts of the mainland U.S.
- No visa required for U.S. citizens
- Familiar banking and tax systems
- Warm weather year-round
- Access to beaches and nature
- Safety is rated higher in Puerto Rico than mainland America
- Pace of life is slower
Cons
- Certain goods may be more expensive
- Imported products can cost more
- Healthcare is often understaffed causing significant delays to treatment
- The fresh fruit and local produce are appealing, but because Puerto Rico follows the same food regulations as the mainland U.S., we don’t expect the overall food system to be dramatically different
Verdict
Puerto Rico is a strong option. We could live on a budget that feels acceptable for us while enjoying the beaches, nature and slower pace of life.
Thailand
Pros
- Potentially much lower housing costs
- Affordable food and transportation
- Ability to stretch retirement or remote-work income
- Highly rated healthcare system
- Warm weather year-round
- Access to beaches and nature
- Many safety rankings place Thailand ahead of the United States, which is reassuring for us
- Pace of life is significantly slower
- The food we experienced in Thailand felt fresher and less processed than what we’re accustomed to
Cons
- Visa requirements and expenses add complexity
- International travel costs
- Currency fluctuations
- Infrastructure varies by region
Verdict
Having to secure a visa and keep up with it was the most daunting part of choosing Thailand. It is the only reason I considered other locations so heavily. I also had a little bit of worry about the infrastructure as a lot of areas are lacking what we are used to. Despite those concerns, Thailand continues to offer the strongest combination of affordability, healthcare, lifestyle, safety, and overall quality of life for our goals.
What Daily Life Seems Like for Each Place
Florida
What daily life seems like:
Daily life in Florida doesn’t seem much different than our current life. We appreciate that living in southern Florida would remove having to deal with winters however, the political climate and faster pace of life don’t align particularly well with the lifestyle we’re hoping to create.
Puerto Rico
What daily life seems like:
Daily life in Puerto Rico does seem slower paced than our current life and the rich culture and foods sound lovely. The instability of the power grid would be challenging especially for digital nomads who rely on the internet for income.
Thailand
What daily life seems like:
Daily life in Thailand is much slower than our current pace of life. There is a beautifully rich culture with some of the best food in the world. Thais have a phrase sabai sabai that translates to relax, chill or everything is fine. That philosophy aligns closely with the kind of life we’re hoping to build.
The Emotional Factor
Facts and numbers matter, but emotions matter too.
When I picture living in Florida I feel slightly stressed. Our main reasons for considering Florida are because my father and step mother live there and not worrying about a visa would be great. However, as nice as it sounds to be near family and not stress about visas, I am more stressed thinking about the overall cost of living and political climate. Despite its higher costs, Florida ranks second because it offers reliable infrastructure, proximity to family, and eliminates the complexities of international relocation.
When I picture living in Puerto Rico I feel delighted by the beautiful scenery, great food and rich culture. However, the unreliable power grid is very concerning. When we move we will be making all of our income online. With an unreliable power grid it could greatly disrupt our income.
When I picture living in Thailand I feel relaxed. I think about day to day interactions with the incredible Thai people and hearing the ocean every day. I picture eating fresh food, spending more time outdoors, and living in an environment that feels healthier and less stressful overall. I do have some anxiety around visas and the ever changing requirements but I feel my excitement outweighs that anxiety.
Current Rankings
#1: Thailand
Why:
Thailand is our top pick! Even with the added stress of visas I think this is the most stress free life we could live. It is also hard to beat the incredible limestone cliffs, turquoise waters and fresh food.
#2: Florida
Why:
Florida is our second choice. Florida has its perks of being closer to family, no winter and having familiarity but it is by far the most stressful option due to cost of living and political landscape.
#3: Puerto Rico
Why:
Puerto Rico is our third choice. Puerto Ricos biggest perk for us is the beautiful scenery and culture. However, I am not super confident about maintaining income with the unreliable power grid.
Final Thoughts
This comparison isn’t final.
The more we research, the more we learn that every destination comes with trade-offs. What matters most is finding a place that aligns with the life we’re trying to build.
Right now, if we had to choose today, we would choose Thailand. Not because it’s perfect, but because it feels most aligned with the life we’re trying to build.
That could change tomorrow, next month, or after our next research deep dive.
For now, the search continues.
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