Which Caribbean Island Is Actually Right For You?

Written By Jennifer Jo De Witt

Photo by Round Hill, Jamaica

The Caribbean gets dismissed as basic beach travel by people who've clearly never been beyond a cruise port. There are 26 countries and over 700 islands here, and lumping them together is like saying Paris and Prague are "basically the same European vibe."

The volume of US travel to the Caribbean last year was the highest since 2019, which tells you two things: the secret's out, and you need to be strategic about where you go. Here's how to actually choose.

If you want to fly and flop

Turks and Caicos. The beaches legitimately live up to the hype—I'm talking soft sand that doesn't stick and water so clear it looks fake in photos. This is not a "let's do all the activities" destination. This is a "bring three books and lower your heart rate" destination. There's excellent diving on the barrier reef if you need to justify the trip, but mostly this is about unplugging.

Direct flights from New York, Toronto, Miami, and Atlanta make it easy.

If you want to see and be seen

St. Barth's is the Caribbean's St. Tropez, which means: chic boutiques, table-dancing at beach clubs, and a scene that requires your best swimwear. The French influence is everywhere—the food, the style, the casual elegance. This is where you go when you want gorgeous beaches and want to get dressed up for dinner. (Tips to Get to the Island of St. Barth’s)

If you need actual adventure

St. Lucia's twin Pitons rising out of the sea are genuinely dramatic—not Instagram-dramatic, actually-impressive dramatic. The island has rainforest hiking, volcano tours, world-class diving, and hillside resorts with views that justify the honeymoon cliché. This is the move if "relaxing on a beach" sounds like a punishment.

If you're feeling romantic

Jamaica gets pigeonholed as all-inclusive resorts, but there's so much more here. Golden beaches, lush mountains, legitimate culture, and hospitality that feels genuine rather than scripted. Round Hill has private villas where celebrities hideout, Rockhouse is a cliffside boutique hotel that punches above its price point, and everywhere you go, the food and music remind you you're somewhere specific, not just "the Caribbean."

If you're bringing the family

Anguilla is 16 miles long, easy to navigate, and has calm, shallow beaches that work for toddlers without boring teenagers. Many resorts have actual kid programs (not just babysitting with a fancy name), and the island's slower pace means you won't spend your vacation managing logistics.

If you're a serious diver

Belize has the largest barrier reef in the Northern Hemisphere. Most Caribbean islands have good diving; Belize has exceptional diving. They just hosted their first Beyond Blue Summit—a national event for marine conservation and sustainable tourism—which tells you how seriously they take their underwater ecosystem. If diving is the priority, not just an activity, this is where you go.

If you lost your passport

Puerto Rico and the US Virgin Islands don't require one. Puerto Rico has vibrant culture, excellent food, and Old San Juan's Spanish colonial architecture. The USVI gives you options: St. Thomas for shopping and sailing, St. John for pristine beaches and hiking, St. Croix for history and a slower pace. Not having a passport doesn't mean settling for less.

If you genuinely can't decide

A cruise lets you see multiple islands in one trip without the hassle of inter-island flights and hotel changes. You wake up somewhere new every day, which works if you're still figuring out your Caribbean preferences. Royal Caribbean, Celebrity, and Princess all do this well.

We didn't start as travel advisors. We started as travelers—the obsessive kind who research for months, take notes on everything, and come home with opinions. Eventually we realized we could do this for other people and actually get paid for it. Now we're certified advisors with FORA, partnered with Four Seasons, Belmond, Rosewood, and more—and we still text each other hotel & restaurant recommendations constantly, like it's a hobby and not our actual job.

Let us obsess over your next trip so you don’t have to. Our number is in the footer.

Jennifer Jo De Witt

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