While these islands are so close, they couldn’t be more different. Each one has a distinct style and so much to do we recommend taking a week or more to experience each.

Read all about the islands below and choose your own adventure.

If you associate the Caribbean with quiet beaches and tranquil sunsets, then you haven’t been to lively Saint Martin and Sint Maarten.

The world’s smallest area of land divided into two nations, this half-French, half-Dutch island’s cultural mix incorporates a rich African heritage and 120 different nationalities speaking 80-plus languages, giving rise to some of the finest cuisine in the Caribbean.

Philipsburg

The colorful capital of the Dutch side of St Maarten, Philipsburg is the perfect stop for a day on shore. Stroll along Front and Old Street bursting with quaint shops and open-air eateries.

Grab a taxi and we’ll zip up the hill just to zip back down—on the world’s steepest zip line! The St Maarten zip line drops more than one thousand feet in elevation along 2,800 feet of cable and serving up spectacular views of the island the entire way down. For the full experience we take a stunning chair lift ride to the top, a tube ride along the winding hill and land at the zip line station for an unforgettable ride to the bottom.

Simpson Bay

Spend an afternoon at the infamous Maho Beach. Standing at the end of a runway, thrill seekers sip cocktails while planes land right above you.

Watch the super yachts dock at sunset while dining on relaxed fare at the St Maarten Yacht Club.

Take a taxi just a few minutes inland to Topper’s Rhum Distillery. The six-thousand foot distillery pumps out about 50 different flavours, with crazy combos like Banana Vanilla Cinnamon, Bacon & Maple Syrup and Jalapeno Lime, and Bubblegum which visitors are free to sample.

Or stay near the coast and explore the Guavaberry Distillery, the legendary folk liqueur of St Maarten/St Martin. It was first made here centuries ago in private homes. It became an integral part of local culture & tradition and is the national liqueur.

Marigot Bay

Beat the heat with a morning hike to historical Fort Louis and sip away the afternoon at Le Wine Bar on the water.

Grand Case / Creole Rock

Snorkel at Creole Rock, a large rock formation with a reef extending towards the mainland. The site is a shallow one and the nearby reef life offers chances to see the rare frogfish, pufferfish, barracuda and many varieties of reef fish.

Taste the local fare at a Lolo—the local nickname for the dozens of small, independent eateries, sometimes right on the beach or side of the road.

Indulge at one of the many gourmet French restaurants with quality wine and a sunset over the water.

Leave the island with the ultimate souvenir: a custom scent to remind you of your time in St Martin. Tijon Perfumerie produces fine perfumes, colognes and skin care items in their on-site lab, and also offers a 60 or 90 minute perfume making class.

Staff guide visitors through the process of selecting scents from their collection of 300 oils, which are then crafted into their very own fine fragrance to take home.

From everything that you might have heard about Saint Bart’s, you’d half expect a red velvet rope to be strung up at the airport. The Caribbean’s most elite, most expensive island lives up to its reputation as an adult sandbox, where the rich and famous air-kiss over glasses of rosé. But it still has charms that make it attractive to the regular folk, from its uncrowded white-sand beaches—22, to be exact—to its distinctly Gallic flair.

Gustavia

The tidy capital of Gustavia, with its gingerbread-trimmed cottages, designer shops, and elegant restaurants, surrounds a yacht-filled harbor. Spend golden hour and twilight strolling the softly-lit streets sampling wine at the open-air bars.

Spend a day scuba diving just off the capital at the Les Petit Saints. The sites offer an array of hard and soft coral and a variety of reef fish. The shipwreck Nonstop which was a well known, luxury motor yacht, sank during hurricane Hugo. Many varied hard and soft corals have taken hold on the steel hull and the wreck is teeming with a large variety of reef fish.

Make a Parrot Head pilgrimage to Le Select, the famed kitschy bar that inspired Jimmy Buffet to pen Cheeseburger in Paradise.

St Jean

A diminutive strip of colorful boutiques and glamorous beach bars reminiscent of the French Riviera, this idyllic stretch is a preferred spot for windsurfing or snorkeling with calm reef-protected waters.

Spend a day at the beach which sits right next to airport and watch flights take off right overhead, or treat yourself to the highlife with a beach bed and ice cold rosé at the famed Nikki Beach.

Anse a Colombier

Get away from the crowds at the beautiful and remote Anse a Colombier. The rocks surrounding Ile de la Pointe, which hems in the bay to the south, are a great place for snorkeling and scuba diving. South of that is an inlet where sea turtles and sea rays are sometimes observed.

At the north end of the beach, you’ll find stairs leading to the top of the hills and a scenic trail that meanders through patches of fragrant lilies and cactuses.

Pronounced Anne-gwilla (rhymes with vanilla), Anguilla is a British-overseas territory with a distinct reggae-vibe. While St Barts is known for the seen-and-be-seen crowds, Anguilla is perfect for those looking to get away. Celebs like Sandra Bullock, Liam Neeson, Ellen DeGeneres and Portia di Rossi are all fans. Even Chuck Norris owned a home at this lush island getaway.

Crocus Bay

One thing that few people know about Anguilla is that it is honeycombed with caves. Cavannagh Cave houses petrified remains of a giant 3400-pound rodent and a chute that drops 60 feet before hitting the water. The large, cool interior of the Katouche Cave boasts a tree growing out of an opening in the roof and the twittering of bats filling the air with their high-pitched squeaks.

On the water side of Crocus Bay we can anchor near the rocky coast and snorkel looking for hidden caves under the surface.

Road Bay

For divers, this island is paradise—Anguilla’s turquoise waters boast seven marine parks: Dog Island, Prickley Pear, Seal Island Reef System, Little Bay, Sandy Island, Shoal Bay Harbour Reef System and Stoney Bay Marine Park.

However, it is best known for the wrecks off the coast of Road Bay. The MV Sarah is the longest at a whopping 232 feet, the wreck of the Dutch cargo ship the Oosterdiep was deliberately sunk upright and is now a popular night dive, and the MV Meppel took part in the “Dunkirk” operation during World War II, when Allied soldiers were evacuated after being surrounded by German troops. Now it is the home an array of marine life as part of an artificial reef system.

Dog Island

A half day sail will bring us to the uninhabited Dog Island. This low-lying patch of sand is part of a marine preserve. We can hike along the rocky coast, paddle board and tube over the crystal clear water, and snorkel the beautiful protected reefs.

Prickly Pear Cay

Prickly Pear to the east of Dog Island are a pair of small uninhabited islands divided by a narrow channel. Like Dog Island, these cays are popular for hiking and snorkeling, but Prickly has the unique bonus of a restaurant on the beach.

Mead’s Bay

After days of snorkeling, diving, and cave hikes, settle in for some luxury at Mead’s Bay. Spend a day lounging on the white sand beach before heading back to Neverland and get dressed up for a celebratory final dinner at Salt, the signature restaurant of The Four Seasons Anguilla.