The holidays are notoriously stressful. From cooking elaborate feasts to buying personalized gifts for the whole family, there’s only one antidote to the pressure: a vacation.
Don’t worry, we’ve taken one more thing off your to-do list by speaking to travel experts about their go-to getaway for the holidays. According to them, you can’t beat the Caribbean. They’ve given us the rundown of which islands they recommend to relieve holiday season stress.
St. Barts
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Colorful homes along the turquoise waters of St. Barts.
This uber-posh French-Caribbean island came up again and again among our travel experts.
“The Caribbean truly comes alive during the holiday season, and for me, St Barts is unmatched this time of year,” said David Zipkin, co-founder and CCO of Tradewind Aviation. “It’s the perfect balance of festive spirit and laid-back luxury. The island has a celebratory energy that’s elegant yet effortless—you’ll see yachts lined up in Gustavia, beachside restaurants hosting joyous dinners, and a community that feels like family. It’s where tradition meets tropical ease.”
Edita Sgovio, VP of Yachts and Villas for Kensington Tours, agreed that St. Barts is a luxury hot spot. “St. Barts has also become one of the destinations we recommend most often to our top clients, simply because it delivers a level of luxury and ease that’s hard to match anywhere in the Caribbean,” she explained. “The island blends that unmistakable French Riviera feel with a relaxed tropical setting, beautiful beaches, incredible food, and an overall atmosphere that feels both exclusive and effortless.”
For Carolita Urrestarazu Dyrssen of NUBA, it offers the best of both worlds. “The island has an incredible mix of sophistication and natural beauty. You can spend your mornings hiking along rugged coastal trails with breathtaking views, your afternoons relaxing on one of its pristine beaches, and your evenings dining at some of the best restaurants in the Caribbean,” she said. “I’ve explored almost the entire Caribbean, but St. Barts is truly one of a kind. The service, the food, the nightlife, the beaches, and that effortlessly chic atmosphere make it completely unique. It feels so European, so distinctly French, yet with the warmth and ease of the Caribbean.”
Turks and Caicos
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Lounge chairs lay along the white sandy shores of Turks & Caicos.
The pristine waters of this tropical island chain are among the best in the Caribbean. Plus, the destination pulls out all the stops during the festive season.
“I always recommend Turks and Caicos to clients looking for a sunshine-filled, easy-to-reach holiday escape,” said Veronica Kastukevich, owner of Custom Travel. “Its calm, turquoise waters and powdery, white-sand beaches are truly some of the best in the Caribbean, and the abundance of nonstop flights from major U.S. gateways makes getting there a breeze.” She added, “For families, Beaches Turks & Caicos is my go-to. It sits right on the award-winning Grace Bay Beach and takes all the stress out of vacation planning with its all-inclusive experience. Their annual partnership with The Elf on the Shelf adds a little extra holiday magic, with festive fun like themed parties and movie nights under the stars.”
Barbados
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A white sandy beach in Barbados.
Looking for something more budget-friendly? Barbados delivers with affordable accommodations, natural beauty, and accessibility.
CEO and founder of Point.me, Adam Morvitz, told Travel + Leisure, “I love Barbados, especially in the winter season when the weather is perfect with low humidity and lots of dry, sunny, and warm days. The Caribbean coast on the west side of the island has some of my favorite beaches in the world—they are so beautiful and peaceful. The Atlantic coast is also stunning and has a more lively, fun vibe, and so many sea turtles, including leatherback sea turtles, the largest turtle species in the world.”
Dominican Republic
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Villas at Eden Rock Cap Cana line the shore.
Another favorite for our travel experts is a destination that caters to all-inclusive lovers and outdoor adventurers.
For Jenn Lee, president and CMO of Travel Planners International, it’s all about the all-inclusives. “My favorite Caribbean island is the Dominican Republic because it’s so relaxing. Most properties are all-inclusive and full-service, with so many levels of luxury to go all in on relaxation and slower travel. A few of my favorites, which we also recommend to our clients, are Hyatt Zilara Cap Cana and Casa de Campo Resort & Villas,” she said.
According to Andrea Lamperini, COO of WeRoad, “The Dominican Republic is a favorite for millennial travelers. It combines wild landscapes, world-class beaches, dense rain forests, top-tier diving spots, and a lively Afro-Caribbean culture.” He added, “You get real variety in one trip. Hike to hidden waterfalls in Samaná. Explore Los Haitises National Park by boat. Surf on the north coast in Cabarete. Dive or snorkel around Bayahibe’s reefs. Then, wrap your days with merengue, bachata, and local street food.”
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