3 Exciting Overseas Winter Vacation Destinations

As winter approaches and the air begins to cool, we all find ourselves daydreaming about warmer climates and exotic travel destinations. If you’re planning to do more than stare at your computer’s screen saver as an escape this winter, you may want to consider these top three winter vacation destinations.

Note: If you can plan your trip outside of peak travel dates (December 10–January 20), you can save a lot of money on accommodation and flights.


Colombia is quickly becoming one of the most popular, must-visit destinations in Latin America as it continues to recover from a history blighted by illegal narcotics. Having visited recently, I found it to be very different from much of what’s portrayed in the media, which often focuses on the country’s turbulent past. Landscapes encompass everything from vast, modern cities, to rural areas of untouched jungle. There’s even a stunning Caribbean coast in the north.

Travel costs in Colombia are low, helped by currency crashes over the past few years against the U.S. dollar. In my experience, midrange hotel rooms start at around $40 per night, and a meal out in a traditional restaurant will cost less than $10.

Medellin, formerly dubbed the most dangerous city on earth, is now a futuristic, lively metropolis that stretches high up into the surrounding mountains, with a springlike temperature year-round. Bogota is the business-minded capital often overlooked by tourists. Scratch beneath the surface and you’ll find a trendy, bohemian city with wonderful architecture and an exciting street art scene. Cartagena on the northern coast offers a fascinating mix of quintessential Caribbean culture, colonial Spanish architecture, beautiful beaches, and a laid-back vibe.

The driest (and arguably the best) months to visit Colombia are between December and March. With balmy weather and clear skies, it might just be the perfect place for you to escape this winter.


A long time favorite for North Americans, Mexico is still one of the most exciting and accessible winter destinations for Canadians and Americans. Beautiful beaches, friendly people, decadent food, and European-style architecture make Mexico a top travel destination for anyone looking to escape for a week or two during the winter months.

I’ve found that if you avoid flying south between December 10 and January 15, you can save as much as 40 percent off of your airfare.

If you’ve been to popular Mexican resorts, but you’re looking for a bit of a change, consider visiting a different town (I recommend Guanajuato, Sayulita, or Puerto Escondido) and renting a guesthouse or a nice apartment on Airbnb.

If you visit the town of Sayulita after January 15, you can find plenty of places on Airbnb for less than $50 a night. Meals will only cost you around $7 each, and if you rent an apartment, you can cook for yourself to shave more money off your holiday costs.

Trinidad and Tobago

The lush tropical islands of Trinidad and Tobago are some of the most glorious in the Caribbean, also making them some of the most visited in the region. Thankfully, the islands were spared the damage suffered by other Caribbean islands from hurricanes Irma and Maria.

December is high season, bringing large crowds, escalated prices, and a considerable amount of rain. However, if you plan your trip for January or February, there is nearly half as much rain, prices drop drastically, and the beaches will be much emptier than over the holidays.

For accommodations, check out Airbnb, where you can often find higher quality private apartments for around $60 per night. A meal in a midrange restaurant will cost around $15 and up.

Most visitors come for the natural beauty, and at this time of year, the islands are covered in lush foliage and tropical flowers. Relax on pristine white sand beaches, discover gorgeous waterfalls, and marvel at the stunning mountains inland. Trinidad and Tobago is also famous for its festivals, which occur year-round. The biggest one, the annual Carnival celebration, falls in mid-February.