10 Favorite Caribbean Islands With Flair, Flavor and Fun

With some 26 island countries, the Caribbean serves up endless vacation options – and over the years, we’ve been lucky to explore many.

We got engaged in elegant Barbados, blissed out in lush St. Lucia, soaked up all-inclusive luxury in Jamaica (can you say dreamy overwater bungalows?) and keep returning to St. Martin/St. Maarten for its French cuisine and chic beach clubs.

Then there are islands we’ve visited on small ship cruises (and are itching to return to stay longer!) – like oh-so glamorous St. Barts and quietly magical Iles des Saintes, a Caribbean secret we’re tempted to keep to ourselves.

For us, the perfect island mixes amazing experiences, charming boutique hotels, fabulous food and, naturally, gorgeous beaches.

So here they are – our favorite Caribbean islands, each with something special to offer.

Barbados naturally holds a special place in our hearts, as it’s where we celebrated our engagement.

It ticks all the Caribbean vacation boxes – and adds a dash of rich history too. Ideal for both adults and families, it’s also arguably the best Caribbean island for older couples, thanks to its sophisticated (yet relaxed) feel.

Bridgetown, the capital, is a UNESCO World Heritage Site, blending colonial architecture with Caribbean energy. Stop by St. Michael’s Cathedral to admire its Gothic arches.

On the west’s Platinum Coast, you’ll find powdery beaches and posh resorts (singer Rihanna owns a villa at Sandy Lane). The rugged east coast, meanwhile, lures surfers to Crane Beach and Bathsheba. Down south, the oceanfront Richard Haynes Boardwalk is great for a sunset stroll.

One reason we can’t stay away from St. Martin/St. Maarten? The food!

This dual-nation island offers two distinct vibes, along with several great places to stay.

On Dutch St. Maarten, Philipsburg is great for duty-free shopping, while Simpson Bay is the go-to for casual beach bars and lively nightlife.

But we’re especially drawn to French St. Martin with its lovely boutique hotels and superb dining.

In Grand Case, dubbed the “culinary capital of the Caribbean,” we’ve savored exquisite French cuisine at gourmet restaurants like Le Pressoir (don’t miss the foie gras with rum and coconut-pineapple) and L’Auberge Gourmande (try the Dover sole meunière!).

Orient Bay, also on the French side, is popular for windsurfing – watch the action from beach clubs along Orient Beach’s long powdery white sands.

We adore Iles des Saintes (commonly known as Les Saintes) – a group of nine teeny secret Caribbean islands off Guadeloupe. So shhh, don’t tell too many people!

The main island, Terre-de-Haut, was settled by French fishermen from Brittany in the 1600s. Today, it’s sprinkled with pastel Creole cottages, seaside cafés, patisseries and charming boutiques.

We visited on a Star Clippers sailing cruise, anchoring off Terre-de-Haut. Most people, though, arrive via a 30-minute ferry from Guadeloupe.

There are no mega-resorts, no beach clubs, no nightlife – just crowd-free beaches (many great for snorkeling) and simple guesthouses or cottages.

To get around, you can rent a moped or golf cart, or simply walk – you won’t get lost on this pint-sized paradise.

We chose Bocas del Toro for one Caribbean trip as it’s decidedly under-the-radar.

Less touristy than other hot spots, this island archipelago is off Panama’s Caribbean coast. (To get there, we took a one-hour flight from Panama City to Isla Colon.)

Bocas is all about nature, adventure and leaving the world behind. Surf, snorkel, hike, spot monkeys – or just swing in a hammock and do nothing at all.

5) St. Barts

Best for couples and French flair

Just 10 square miles, St. Barts (short for Saint Barthelemy) oozes French Riviera glam with a tropical twist. This swanky celeb-favored island is all about refined boutique hotels, chic beach clubs and beaches with sand as soft as flour.

Start the day with a buttery pain au chocolat, slip into your designer resort wear and ease into a leisurely lunch – with a bottle of rosé – toes buried in the sand.

We’ve visited on several cruises (not flown in yet!). But aviation buffs will tell you landing here is part of the thrill. Tiny turboprops swoop in to one of the world’s shortest and most dramatic runways.

Gustavia (the port town) and Saint Jean are the island’s main hubs. In Gustavia, we’ve browsed luxe boutiques with gasp-worthy price tags on our way to scenic Shell Beach.

Puerto Rico is an archipelago with a main island, four smaller ones (like Vieques and Culebra) and hundreds of cays. And as a U.S. territory, no passport is needed for Americans!

It bursts with color, rhythm and history.

We were wowed by Old San Juan’s candy-colored buildings, blue cobblestone streets and massive forts. Wandering its plazas feels like stepping into a vibrant painting, especially when a street party breaks out. Add in James Beard-recognized restaurants and the vibe is irresistible.

Beyond the capital, you can kayak in glowing bioluminescent bays, hike in lush rainforest and laze about on glorious beaches.

Then there’s its great food scene – from local mofongo and crispy tostones to a new wave of splendid farm-to-table dining.

After getting engaged on Barbados, we spent a blissful week on St. Lucia – so, like Barbados, this emerald island is particularly special for us.

One of the most beautiful islands in the Caribbean, it dazzles with rainforest-cloaked mountains, cascading waterfalls, black-sand beaches and its iconic twin green peaks – the UNESCO-listed Pitons.

For a unique perspective, ride Rainforest Adventures’ Aerial Tram above the jungle. Cage-like gondolas soar 120 feet (37 meters) above the canopy, as guides point out orchids, hummingbirds and more.

Beach lovers will swoon over Sugar Beach, a white-sand beauty tucked between the Pitons.

And if you’re after Caribbean hotels with private pool suites? St. Lucia has plenty.

When it comes to luxury escapes, Jamaica is easily one of the best Caribbean islands for honeymooners. It’s famous for its deluxe couples-only resorts – hello, Sandals!

Not surprisingly, this is also the island where you’ll find some of the Caribbean’s finest overwater bungalows, complete with glass floors, infinity pools and private butler service.

But beyond sipping rum punch at your resort, Jamaica serves up iconic island experiences – think reggae beats, lush mountains and palm-lined beaches.

If you love life on (and under) the water, you’ll fall for St. Vincent and the Grenadines. This eastern Caribbean nation is made up of 32 lush islands with volcanic black-sand beaches and colorful coral reefs teeming with life.

We first visited while staying at the (now-closed) Club Med on St. Lucia, flying to tiny Union Island to board a sailing cruise through the Grenadines.

We’ve since returned on small cruise ships. Star Clippers and Windstar Cruises drop anchor at tiny pristine islands like the Tobago Cays, where the snorkeling is sublime.

Janice even went lionfish hunting near Mayreau with Tradewinds, scuba diving to help remove this invasive species. Bonus: Lionfish is delicious grilled!

For star-studded solitude, head to exclusive Mustique, where Princess Margaret once owned a villa.

You won’t find cruise or other crowds in the Grenadines – just gin-clear bays, swanky villas and some of the prettiest anchorages in the Caribbean.

Looking for the Caribbean island with the best beaches? Antigua claims the title – with 365 of them! From long ribbons of soft white sand to secluded coves lapped by turquoise waters, it’s beach heaven.

Dickenson Bay is the liveliest, lined with resorts, beach bars and watersports. Valley Church Beach is quieter, perfect for relaxed swims in clear calm water.

Needless to say, watersports – from sea kayaking to sailing, snorkeling and stand-up paddleboarding – are popular all around the island.

Now you know our favorite Caribbean islands!

So there you have it – our hand-picked list of the 10 best islands in the Caribbean. Whether you’re dreaming of powdery beaches, French flair, lush rainforests or stylish resorts, each island offers its own unique magic. Which one is calling your name?

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