Your Caribbean Matchmaker

Last year, the volume of US travel to the Caribbean was the highest it’s been since 2019, and the bookings haven’t slowed down. As the weather starts to cool, it’s time to start planning your next sunny getaway, and my Caribbean matchmaker makes it easy to choose where.

Find Your Match

If you want to fly and flop

Ideal for beach purists, Turks and Caicos Islands are home to some of the most beautiful beaches in the world. Think soft sand and clear blue waters. There’s excellent diving on the barrier reef and prime birdwatching in the nature reserves, but for the most part these islands are all about unplugging and soaking up the sun.

Direct flights from major cities like New York, Toronto, Miami, and Atlanta make Turks and Caicos a convenient option.

Ultra luxury: Amanyara
Family-friendly: Grace Bay Club
Under $500: West Bay Club

If you want to see and be seen

If you love St. Tropez, St. Barth’s is your pick. Best for luxury travelers and romantic getaways, it’s the Caribbean’s very own slice of the South of France. Your days will be spent shopping in chic boutiques, savoring meals at buzzy restaurants, dancing on tables at chic beach clubs, and of course, enjoying time on the gorgeous beaches.

Ultra luxury: Eden Roc St. Barths
Family-friendly: Rosewood Le Guanahani
Sustainabile: Hôtel Manapany

If you’re looking for adventure

With its iconic twin peaks—Gros Piton and Petit Piton—rising above the sea, St. Lucia is one of the Caribbean’s most dramatic islands. Gorgeous views from hillside resorts set the perfect scene for romantic trips like honeymoons, and the rainforest paired with mountain is a great choice for adventurous, active travelers. If water sports are more your thing, the island also has world-class diving and numerous boat excursions.

Ultra luxury: Sugar Beach, A Viceroy Resort
Wellness focus: Bodyholiday
Under $500: The Landings Resort and Spa

If you’re feeling romantic

With golden beaches, lush mountains, and sunsets that seem to glow just for two, Jamaica offers endless ways to connect. Add in its lively culture and warm hospitality, and Jamaica sets the stage for unforgettable moments together.

Ultra luxury: Round Hill Hotel and Villas
All-inclusive: Moon Palace Jamaica
Under $500: Rockhouse Hotel

Or bringing the family

Small, safe, and easy to navigate, Anguilla is a great option for families or multi-gen getaways. The island is only 16 miles long and offers calm, shallow beaches that are safe for young kids, while big kids can snorkel, kayak, or paddleboard. Many of my favorite resorts also have kid-friendly programs, and the warm hospitality and slower pace make families feel at home.

Ultra luxury: Belmond Cap Juluca
Family-friendly: Four Seasons Anguilla
Under $500: Aurora Anguilla Resort and Golf Club

If you‘re a diver

While the majority of Caribbean islands have excellent diving, Belize stands above the rest for travelers who want to highlight diving on their trip. Belize is home to the largest barrier reef in the Northern Hemisphere, with an impressive array of sea life. Fun fact, this past September Belize hosted its first national event dedicated to diving and marine conservation. Beyond Blue Summit was open to sustainable tourism leaders and marine conservation experts, as well as certified divers, sealing the island’s reputation as a top diving destination.

Ultra luxury: Turtle Inn
Adults-only: Matachica Resort & Spa
Under $500: Alaia Belize, Autograph Collection

Maybe you lost your passport…

If you haven’t gotten around to getting a passport, there are still great options. Puerto Rico blends Caribbean beauty with vibrant culture, while the USVI (St. Thomas, St. John, and St. Croix) offer something for every traveler: St. Thomas for shopping and sailing, St. John for pristine beaches and hiking, St. Croix for a dose of history and culture.

Or you just can’t decide

A cruise is one of the best ways to see the Caribbean because it allows you to experience the variety of the islands in a single trip. Instead of choosing just one destination, you can wake up in a new port every day. Some of my favorite cruise lines for exploring the Caribbean include Royal Caribbean (obviously), Celebrity Cruises, and Princess Cruises.