Escape the Winter Chill on the Tropical Island of Barbados

Take a train ride to a rum distillery, catch a wave on white-sand beaches, and make friends with the resident green monkeys—all before tourist season heats up on this culturally rich Caribbean island.

The striking coastline of Bathsheba Beach. / iStock

Getting There

JetBlue offers weekly nonstop service from Logan on Saturdays only, which makes planning your itinerary that much easier.

Staying There

It’s hard to find a more quintessentially Caribbean place to lay your head than St. Peter’s Bay Resort & Residences, situated on the island’s western “platinum” coast. A 30-minute drive north from the bustle of Bridgetown, Barbados’s capital city, the luxe accommodations include one- to five-bedroom villas perfect for every sort of escape, from romantic getaways to multigenerational vacations with the fam.

A patio with a view at St. Peter’s Bay Resort. / Photo courtesy of St. Peter’s Bay Resort & Residences


Barbados has a reputation for having some of the best surfing in the Caribbean, and thanks to warm waters and consistent breaks, it’s also a great place to learn. Beginners will want to hit the island’s calm southwest beaches, where instructors from Barry’s Surf School will have you riding the waves in no time. (If you’re visiting November 9 to 17, get inspired for your lesson by watching the sport’s most elite athletes hang 10 at the Barbados Pro, held at Bathsheba’s legendary “Soup Bowl.”) After hitting the water, tuck into a couple of grilled fish sandwiches, a.k.a. cutters, at Bridgetown’s world-famous Cuz’s Fish Stand before traveling north to the Barbados Wildlife Reserve, where you can catch a glimpse of the area’s most mischievous resident: the green monkey.


Once the afternoon sun starts to beat down, consider a breezy hourlong ride aboard the newly built St. Nicholas Abbey Heritage Railway, which takes you from a 1658-built plantation and rum distillery through woodlands rich with mahogany trees up to scenic Cherry Tree Hill, where you can drink in panoramic views of the Atlantic. Worked up an appetite yet? Enjoy dinner with a drop-dead-gorgeous view at the Cliff, perched atop a dramatic bluff overlooking the ocean in St. James Parish. And no Barbados trip would be complete without a nightcap at the Rum Vault at the Colony Club resort, which has 150 varieties of rum in its collection—the largest on Barbados. Don’t feel pressured to try them all: You’ll need to book several return trips to paradise for that.