How To Winter In The Caribbean Without Having To Be Wealthy (Or Retired)

Tracy - Puerto Morelos, Mexico
Exploring the streets of Puerto Morelos, Quintana Roo, Mexico.

The summer warmth is fading fast, the days are getting shorter and the crisp, fall air signals what’s to come. Yes, it’s that time of the year again to think about shoveling snow, scraping ice, and trying not to skid down the sidewalk (on your bottom), while losing all feeling in your fingers, nose and toes from the icy, bitter cold north winds.

But it doesn’t have to be like that. You could skip winter and head south. Instead of shivering and shoveling, you could raise a margarita while relaxing on white sand beaches in the Caribbean.

Maybe you have a dream of spending weeks or months at a time living in exotic places like Thailand, or trekking through Europe. Does this sound like something you could only do if you were ultra-rich, won the lottery, or in about 30 years IF you can afford to retire from your job?

Well, you don’t need to wait for retirement age to winter in the tropics or travel the world. You don’t need to be a millionaire, either.

My husband and I spent six months (from November through April) in 2010/2011 living in Mexico’s Yucatan Peninsula where the average winter-time temperature plummets to the mid to upper 80’s and the sun shines bright every day. (I can’t believe this was six years ago!!!)

When we planned this trip, we had absolutely no savings, and I had been laid off from my job six months prior – so money was tight.

All of this didn’t matter because we planned a strategic relocation rather than an extended vacation.

Palm tree with boats.
Palm tree with boats in Puerto Morelos, Mexico.

Prerequisites: How To Make This Possible For You

For most of us, we are tied to one location all year due to our job. So in order to take an extended trip, or a short-term (or long-term) relocation, you need to either:

  1. Separate your income from your location. That means get a job that you can work remotely, or negotiate a remote-working agreement with your boss.
  2. Create a business that allows you to live and work from anywhere. My blog made this trip possible.
  3. Save your pennies! But you don’t need a whole lot. Our living expenses maxed out at $1,300 USD per month, and we lived quite comfortably. So for six months, our cost was $7,800 USD (plus airfare).

The Cost of World Travel: Vacation vs. Relocation

World travel, or the thought of living abroad, sounds expensive. When it comes to cost, a two week vacation is very expensive. Many people spend hundreds or thousands of dollars to stay briefly at a resort, eat out for almost every meal, buy souvenirs, and treat themselves to luxuries they don’t allow themselves back home. Total this up, and a one or two week trip has a hefty price tag.

While it costs an arm and a leg to visit a foreign country, or to take a cruise, or spend a week or two at a luxury resort, it can often be cheaper to live there instead.

Here’s a prime example: My husband and I spent just four nights in an all-inclusive resort in Playa del Carmen, Mexico for our honeymoon in 2007 and the total budget for our trip minus airfare was about $1000. Pretty decent, but that’s a cost of $250 per night! And we could only afford to stay 4 nights.

In November 2010, we spent an entire month of comfortable living 1.5 miles (or a $1.60 USD cab ride) from a postcard-perfect beach in Puerto Morelos (about 25 minutes north of Playa del Carmen) for the same $1000 – that’s $1000 for a full month of living expenses!.

This included our rent for a beautiful cabana surrounded by jungle gardens, food (including eating out more often than we did back home), cab rides, and luxury bus rides into Playa del Carmen or Cancun twice per week, and everything else we needed to maintain our lifestyle that we were accustomed to back home.

Of course we didn’t have all the luxuries of an all-inclusive resort (although they were all available to us at a higher budget), we did have an entire month to enjoy the beach and the sunshine instead of only 5 days – and for the same price we paid for our little binge trip three years before.

When you think in terms of temporary relocation rather than vacation (resorts, hotels, restaurant meals), the price tag of your trip plummets.

Blogging from Mexico
Despite living about a kilometer from a postcard-perfect Caribbean beach, I still had to blog to pay the bills.

The Cost of Lodging Abroad

In November 2010, we stayed in a comfortable, cabana in Puerto Morelos, Mexico for a monthly rent of only $345 USD and that included all of our utilities. This wasn’t an odd deal or a rare find either, and no, it wasn’t a hut in the jungle with no electricity or toilet.

How did we find such a nice place for so cheap? Craigslist! Go ahead and see for yourself. Look at apartment and temporary/sublets in a country you want to visit. Some countries are very inexpensive such as Mexico (Yucatan), Costa Rica, Panama, Nicaragua, Thailand or even some countries in eastern Europe. You’ll be amazed at what you find. If the price is in a foreign currency, use an online currency converter to help decipher the price in US dollars, Euros, or whatever your currency is.

Caution: There are rental scams on Craigslist, so use common sense on the platform. For example, a picture-perfect 5-bedroom home with a pool on the beach for $400 USD/month is probably too good to be true. Research who you rent from!

Using Craigslist, I’ve found houses for rent in Costa Rica for the cost of one-bedroom apartments in the United States. If you aren’t afraid to rough it a bit, you can find places to live right on the beach or nestled into the jungle for dirt cheap. If you’ve got a higher budget, you can seriously upgrade your standard of living while paying the same amount that you are currently paying for rent.

Our one bedroom apartment in Chicago from 2008-2010 cost almost $900/mo plus utilities. When planning my trip, I found quite a few 3-bedroom beach houses in Central and South American countries for that price, with utilities and maid service included!

After our stay in Puerto Morelos, we rented a beautiful, air-conditioned, 2-bedroom apartment in an upscale neighborhood in Merida. We were in a gated property and had three balconies overlooking gardens and fruit trees. We were walking distance to absolutely everything – including the beautiful Paseo de Montejo boulevard with tons of things to do. The cost of our apartment was $500 USD per month! This apartment was no dump either. It was fully furnished, very clean, and modern.

Merida house.
Our rental in Merida (pardon the big-ol’ gate).
View from balcony.
The view from the upstairs balcony was often breathtaking! I’d sit out there and enjoy blooming flowers and wild parrots – in February!

Cost of Living Abroad

Besides finding nice apartments and houses to rent month-by-month in beautiful, tropical locations that cost less than what you are currently paying, the cost of living in many countries is much less than in the US, Canada, or Europe.

During our six-month stay in the Yucatan peninsula of Mexico, Davy and I ate all of the ripe, delicious tropical fruit we wanted for a fraction of the cost we’d pay in the states. We’d buy a bag of 21 ripe, delicious, locally-grown tangerines for 5 pesos (40 cents). We’d take a daily trip to the corner fruit market to fill a large grocery bag with the freshest pineapples, papayas, fresh-squeezed fruit juice, bunches of bananas, and other delicious, exotic fruits and never had to pay more than 100 pesos (about $8).

We ate at restaurants in Puerto Morelos for as little as $4 USD – for both of us including appetizer and drinks! Don’t be afraid to eat at local restaurants. There’s always a risk of food poisoning, whether you are eating dinner in a foreign country or at a fast food joint back home. Our first restaurant experience in Puerto Morelos was at a family-run place with a dirt floor, no electricity, geckos scurrying around us, and an 8-year-old waiter. It was lovely!

We didn’t need a car either as everything we needed was within a very short walking distance from where we were staying. When we didn’t feel like walking, we took a cab for about 20 pesos ($1.60 USD) to the beach or anywhere in town. (In Merida, you can get across town for 60-80 pesos ($5.00-6.50 USD). In Chicago, $6.50 takes you 4 blocks!

We took luxury, air-conditioned Mercedes buses (that also showed movies) to either Cancun or Playa del Carmen for only 20 pesos per ride. If we didn’t want to wait 10-20 minutes for the next bus, we’d spend the same amount or less for any of the many express shuttles or Colectivos that run up and down the highway all day long.

Everything from household goods to medical and dental care can be much, much cheaper in other countries while offering the same quality and level of care and service as you’d expect in the States (often, it’s better, more attentive medical care than you’d get in the States). A trip to a dermatologist in an upscale plaza cost just 500 pesos (just over $50 USD) out of pocket, without insurance.

On average, our monthly cost of living in Mexico during the winter of 2010/2011 was just under $1300 USD per month – for both of us!

Christmas abroad.
Living in a foreign country is a rewarding experience, but it can also be lonely – especially during the holidays if you can’t fly back to be with family.

The “Escape Winter/Travel The World Without Being Rich” Plan

It might feel like wintering in a tropical country or traveling abroad is a daunting task, nearly impossible to do on your budget. But it’s not. It’s a relatively simple, straightforward process that I’ll show you below.

Tracy on the beach.
Ah! The beach!

Step 1: Find an Inexpensive Country

The first step is to find a country to live in that is both inexpensive and safe. As far as cost of living, countries in Central and South America can be a real bargain (Mexico, Costa Rica, Panama, Argentina). Some countries in Europe and Asia (especially Thailand) are cheap as well.

As with anywhere in the world, prices range from ultra-luxurious vacation rentals geared toward North American and European travelers costing in the thousands per week to ultra-rustic, bare-bones shacks for a couple hundred per month.

Of course, you should do your research on any country before you decide to go there. Look into the actual cost of living in these countries (and don’t fall for the “live like a king on $400/mo” pipe dream). Find out how much it will cost to rent a nice place (and how available places are for rent there). Also take a look at safety and general political stability in any country you go to.

Try not to read too much into scary news headlines or paranoid, bitter traveler reports of those who were victims of petty crimes. I had lived in Chicago for three years prior to my Mexico trip and the news headlines there were often filled with shootings, violence, and other crime. It’s all a matter of where you live and making sure you don’t live among the crime-infested areas of a city or country.

Use common sense and stay alert, and chances are nothing bad will happen to you. Staggering through unfamiliar streets at night from the bar to your rental will dramatically increase your risk of being targeted. Just act like you belong and know where you are going, and you’ll be fine.

Also, be sure you read up on immigration and tourist visa requirements. Some countries will allow you to stay up to 6 months while others allow much shorter stays. Some countries require certain immunizations.

Chichen Itza
The pyramid at the famous Mayan ruins of Chichen Itza.

Step 2: Find Lodging

This is much easier than it sounds. There are quite a few websites that have listings for short-term rentals in foreign countries, but I used Craigslist exclusively to find the places we stayed while in the Yucatan. You have to be very careful, though, dealing with people online, especially on Craigslist because scammers use the service to target naive travelers.

I could write a whole blog post on avoiding scams. Just use your common sense, and if a deal seems too good/cheap to be true, or they seem over-eager to find a place for you, run the other way.

The best method for finding a place to live is to book a few days to a week in a hostel or hotel, then use the time there to find a more permanent place. I am extremely leery about securing a place to live for more than a week or two site-unseen.

Although, prior to landing in Mexico, we booked an entire month at our place in Puerto Morelos, and then booked a place (with only seeing photos) for six weeks in Merida before finding our beautiful apartment I described above. Use your judgement and realize that you might have to be a little flexible and/or tolerant. Everything worked out well for us, though.

Three great resources for finding lodging is:,, Look into Airbnb, too.

Step 3: Find Airfare

Cheap airfare is increasingly becoming a challenge to find. What I usually do is search for “Flexible Dates” on Travelocity. You can dig up some amazing deals on airfare if you’re not locked into flying on a certain date.

Google terms like “travel hacking” for tips on saving money with airfares, and getting travel discounts.

Booking well in advance, or arriving at your destination during the “off season” can save money, too. We arrived in the Yucatan at the tail end of the rainy season, and before the busy tourism period, so our airfare was less than it would have been had we flown in January.

Unfortunately, fees are getting higher and more prevalent with airlines. Even a super cheap ticket might not be so cheap once you pay the checked bag fees and other taxes and fees. Be sure you know what other fees you’ll be charged before you purchase your ticket.

Playa del Carmen
My hubby and I enjoying drinks in a “boat” seat at a cafe in Playa del Carmen.

Step 4: Keeping Expenses Low

Stay out of expat communities and tourist areas. While you might be tempted to surround yourself by the familiar, the prices in these neighborhoods and communities will be geared toward tourists with higher budgets.

In Puerto Morelos, we didn’t stay right on the beach or in the “tourist zone”. Instead, we opted for a more authentic (and ultimately more rewarding) experience in the actual village where the locals live. There were still other expats living among us but we all enjoyed local, Mexican prices (much cheaper than the “tourist prices”) on food, necessities, and restaurants.

Besides, you’ll get a more authentic experience living among the locals. Even though our winter-long trip to Mexico was our second time in the country, it felt like it was our first time since we had only experienced the “artificial tourist version” of Mexico previously.

Figure out what is most important for you in order to feel that you are living comfortably while still keeping your expenses low. You don’t need to live in a dilapidated shack in the jungle, but also realize that trying to replicate a luxury North American lifestyle abroad won’t always save you enough to make it worthwhile. Besides, what’s the point of moving to a beautiful Caribbean beach if you are going to spend your time watching TV on a giant plasma screen or zoned out in front of your gaming console or iPhone?

Fruit stand in Merida.
This was my favorite place to get fresh fruits and green juices in Merida. I also discovered the mamey sapote and fell in love with this fruit!

Step 5: Establish Realistic Expectations and Be Adaptable

Some of the things you read online make it sound as if the second you step off the plane, you’ll be living like a king for pennies. Or that life in a tropical country is nothing but white sand, turquoise water bliss 24/7. It isn’t. There’s a big difference between visiting a place and living there.

Be sure to read my followup post about the realities of living in a tropical location where I discuss the pros and cons of living abroad – why you should definitely do it, and why it sometimes sucks.

Geckos are the cute visitors, but you may also get large bugs and spiders coming inside to say “hello”. That’s just part of life in the tropics.

Step 6: Funding Your Trip

We decided to make our relocation abroad a long-term adventure (initially, it was going to be a year-long or longer trip, but turned out to be only six months). Because of this, we sold almost everything we owned which provided a lot of cash to help fund our trip. It also added a comfortable cushion in our savings account so that we could be at peace knowing that we wouldn’t have to worry about finances for a while as long as we stuck to our budget.

The best way to maintain a worldwide-travel lifestyle long term, however, is to find a way to make a living online with a website. Imagine if you could make the exact same amount of money you make right now (or more), but you didn’t have to go anywhere in order to bring in this income. Imagine if your paycheck came from work you did from your computer, and it didn’t matter if your computer was in Chicago or Bangkok or Paris. If you had no job to go to, you can really live anywhere.

The beauty of this plan is that you can work from an internet connection from anywhere in the world while selling products and promoting affiliate products from your website. You can then spend that money abroad in less expensive countries, living better than you could back home for the same amount.

Wild monkeys!

In July 2009, my husband and I launched Incredible Smoothies (now By July 2010, we were only earning a few hundred dollars per month from the website – not enough to live on, even in a third world country. But the income was growing and we were getting ready to release our first program (which later become Reset 28).

By February 2011, we were earning enough from our website to live comfortably in Mexico (which we were at the time). By June 2011, we were making enough to live back in the States.

(You see, relocating abroad could help you quit your job and live off your website sooner. The six months we spent in Mexico gave us the opportunity to accelerate the growth of our business in a place that didn’t require a high cost of living. Wintering in the tropics can often be a sound financial strategy.)

Before we purchased our house, we were in a position where we could actually save money by relocating over the winter, or living outside of the country – if we wanted to. Even now that we are homeowners, we could still relocate while subletting or renting our home, or simply pay the mortgage while enjoying new cultural experiences. Just because you own a home doesn’t mean you can’t do extended travel!

Your cost of living can be flexible – especially if you are renting, and that’s a great asset when you are making a living without a job that requires your physical presence Mondays through Fridays.

Barefoot in January: White sand and no snow!

Step 7: Pulling The Trigger On Your Travel Lifestyle Dreams

Ultimately, you need to decide that you want to travel the world and escape winter. You need to also give yourself permission to do it. Then you need to orient your entire lifestyle around achieving that goal.

For us, that meant selling most of our belongings, reducing our expenses, embracing minimalism and making it a priority to create a location-independent income that would allow us to maintain our travel lifestyle.

Would I do it all over again now? Probably not, but that’s me. I would definitely use these same strategies to take a month-long trip or even slightly longer, however.

When you plan your first trip, consider making it a short term relocation. Try a three to six month relocation and see how it goes. Our initial idea was to relocate to Central/South America for up to 5 years, but after six months, the cultural and social isolation caught up with us.

Each person is different in their needs. Some people truly thrive and become entrenched into a foreign culture quickly, while others need regular doses of “home life” between trips.

So instead of committing to a year or longer on your very first relocation experience, plan it for a few months first. You can always extend your trip or take another one.

¡Buen viaje!


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2 thoughts on “How To Winter In The Caribbean Without Having To Be Wealthy (Or Retired)”

  1. Thank you sooooooooo much. This article was very informative. My husband and I have done a lot of talking about spending 6 months a year in Mexico but we need to find an affordable way to do it. My goal is to be able to accomplish this dream 5 years from now. Thanks again

  2. That was a lot of really cool and interesting information. Sounds like something we may want to try out sometime! Thank you!

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