The sun-kissed latitudes of the tropics may seem further and further away as the winter days get darker and colder, but in our shrinking world a sunny weekend getaway is never as far as you think.

Most of us weather the winter months believing that a quick rejuvenating jaunt somewhere warm is too distant, too expensive, or just plain out of reach. This was probably true even just five years ago; but in the meantime we’ve transitioned into a new era of travel, in which we’re all walking around with a pocketful of travel-hacking apps, and dramatically dropping airfares implore us to board a plane and soak up the sun stat.

If the thought of a romantic winter getaway gives you the chills, turn your wanderlusting gaze south to look at the Caribbean.

For under $300 round-trip, you can get from most major US airports to the Caribbean and back. You can go budget backpacker style, sleeping in a hostel and grazing on street food while you wander the streets of a new destination, or you can use the extra room in your budget to splurge on the star treatment.

However you spend your winter escape, try it out in one of these four affordable, easily reachable, and gloriously tropical Caribbean destinations.



Mexico’s Yucatan Peninsula sort of reaches out into the Gulf towards Florida, and if you look hard enough and squint, it’s almost like Mexico is curling its index finger in a “come here” gesture inviting you down for a weekend out of the snow.

A classic destination for American winterbirds, Cancun is easily reachable, reasonably priced, and most importantly, never runs out of sunshine. Get packed for your beach vacation and spend a long weekend lounging on Playa Delfines near the Iberostar Cancun resort, or pop down to Playa del Carmen and set up shop at one of the dozens of hostels within walking distance of the sand. If you’ve got a roomier schedule, make an adventurous day trip down to the Mayan ruins at Tulum.

Cheapest departure airports: Miami, Dallas, Detroit, NYC, Chicago

Low-cost carriers with service to Cancun: Jetblue, Frontier, Spirit, Virgin America, Southwest


winter weekend getaways

Once illegal for US citizens, travel to Cuba sailed past off-the-beaten-path hipster destination and almost immediately exploded into the travel mainstream in the last couple of years. And at just over 200 miles from Miami, it’s one of the closest and most inviting places to spend a weekend thawing out and stocking up on some much-needed vitamin D.

The Cuban capital of Havana has become exceedingly easy to reach by plane or cruise in recent years, but there’s also more to the Caribbean’s largest island than the tourist districts of historic Havana Vieja. Treat yourself to a café cubano upon arrival and then shove on to the best beaches in Baracoa or Varadero. Once you’ve seen enough of the main island, take a boat across the narrow straits to idyllic Isla de Juventud, where you can go diving or keep it simple sipping cocktails in your lounge chair.

Cheapest departure airports: Miami, Orlando, NYC, Boston

Low-cost carriers with service to Havana: Jetblue, Spirit, Frontier


weekend winter getaways

Far from the street art of Bogotá, Cartagena is Colombia’s vivid and vibrant tourist outpost on the Caribbean; and despite being all the way on the other side of the sea, it’s one of December’s cheapest sunny getaways.

Spend your days walking under nonstop sunshine, walking between and upon the city walls and taking in the Spanish colonial architecture of the historic city center. You can walk up the Bocagrande peninsula to catch some rays by the beach, but the better choice is an hour south on Playa Blanca, where a couple dollars will rent you an overnight hammock just steps away from the aquamarine waves rushing up out of the Caribbean Sea.

Cheapest departure airports: Tampa, Orlando, Miami, Atlanta, NYC

Low-cost carriers with service to Cartagena: Spirit, Avianca, Jetblue

The Florida Keys

weekend winter getaways

Sometimes the depth of winter makes you feel like you’re stuck in a frigid world somewhere far from the center of the solar system, but actually you don’t even have to leave the country to feel the heat of the sun again.

The Florida Keys are home to some of the best beaches in the Sunshine State. You can fly into Key West and spend your weekend flip-flopping around the historic district under the shade of palm trees, or visit any of the quieter yet oh-so-splendidly-sunny keys leading back up to Miami. Islamorada and Key Largo are popular among Floridians, but all that really matters is that you enjoy fresh conch fritters and a proper key lime pie while you’re there.

You’ll be able to fly into Key West from New Orleans, Charleston, and Atlanta, as well as other major Florida airports, for around $300 round trip; but you’ll do better by finding a cheap flight to Miami from anywhere in the country and busing or boating the rest of the way.

You can reach either Key West or Miami at a reasonable price from most major US cities and carriers.