My husband has been sailing the deep, blue seas of the Caribbean for the past 30 years. He and his sailing friends have been to 95% of the islands…several times. So who better to ask, “Which are the best islands in the Caribbean?” By “best,” I mean no large cruise ships, no water slides, nothing resembling Cancun, no high-rise hotels, little-to-no pretense, relaxing and transporting. So here are the best, from one who knows!

Top Five, in no particular order

• St. Barth’s—The Sophisticate with Retail and Restaurants

St. Barth’s charming small capital city, Gustavia, has narrow, old streets lined with sophisticated little boutiques, charming Caribbean cottage architecture, and nice little restaurants around the harbor. BUT St. Barth’s is mostly a wild, windswept island with some lovely hotels, beaches, and houses tucked here and there, i.e., not overly developed. St. Barth’s has some great restaurants (like Maya’s and Tamarin). St. Barth’s has it all…with just the tiniest bit of pretense here and there, but you really have to look for it.

You can stay at a hotel or rent a “villa.” If you want to be in a town, check out Eden Rock-St. Barths (charming, fun; Conde Nast Traveler 2017 likes it, too). To get away from it all and experience St. Barth’s wild wonderfulness, go to Hotel Le Toiny St. Barth (in a beautiful natural setting and very stylish; 14 villas on 42 acres; Architectural Digest 2016 also endorses it). Hotel Le Toiny’s DR overlooks the pools which overlooks a big sweep of green on a big crescent of beach…

If you’d prefer to rent a house, WIMCO will take good care of you. Below is Cap au Vent, the house we rented several times via WIMCO. Upon our arrival, the charming caretaker couple (they live on the property but stay to themselves at the far end) had made dinner for us and left it in the fridge to warm up at our convenience, along with a good bottle of champagne. In the morning before we woke up, they delivered just-made croissants from the local bakery…and left us alone for the  day. Houses w/out live-in caretakers are available, too, and WIMCO provides on-island help should you have questions about your “villa.”

Note: Most houses and hotels on St. Barth’s are not on the beaches. They are in the hills where the views are spectacular and the breezes are cooling. This island is very small, so you are never far away from one of the beautiful, unspoiled beaches. You will need to rent car. The roads are narrow and steep but you will get the hand of it quickly.

• St. Lucia—Most Geographically Distinctive

Thanks to the Pitons, its twin-pointed mountain peaks, St. Lucia is the most geographically distinctive island in the Caribbean. This lush, jungle-y island has good scuba diving, beaches, hiking and some really nice hotels. Stay at Ladera! It is spectacularly situated in the saddle between the two Pitons (not on the beach but it has an arrangement with a beachfront hotel for use of its beach), with sweeping views down the verdant mountains to the beach. If you don’t stay here, definitely go for drinks and dinn. It’s the most dramatically beautiful place I’ve ever dined in the Caribbean…and, bonus, the food it good!

If you would rather stay on the beach, book Anse Chastanet because it has a fun beach bar and cheery open cottages built up the mountain.

• Saba—Old-Time Caribbean Loaded with Charm

Saba is the most unusual island in the Caribbean. The island is a dormant volcano sticking straight up out of the water. Saba’s small villages are in the caldera, not on the water because the island is too vertical. They are picture-perfect, neat, clean, and quaint. The only road is called “The Road” and Saba’s capital is called The Bottom because it sits in the bottom of the caldera. While its population is under 2,000 people, a world-class, respected medical school was established on small Saba in 1992 and has 250 students. Unusual, in the best way!

Though Saba has no beaches, it has good diving!

The hiking on Saba looks glorious: 14 trails through lush green forests with big ocean views, abundant wildlife, and fairly cool temp’s because everything here is up, up, up.

While not designer-chic like those on St. Barth’s, Saba’s hotels are small, clean and nice. I haven’t stayed at any of them but Saba’s tourism website will get you started (Queens Garden Resort and Haiku House look promising). Saba is simple living at its best, where you dive, hike, explore the villages, and laze by the pool. Ahhh….

• Iles des Saintes—Laid Back, Authentic, Unspoiled…& Colorblind

Off the coast of Guadeloupe, the Saintes are a group of small islands, two of which are inhabited, Terre-de-Bas and Terre-de-Haute (referring to the winds). Take the 15-minute ferry from T-de-H to T-de-Bas, as it’s fun to explore them both. They are uncrowded, with lovely beaches and snorkeling, simple towns with charming little bars and cafes. Neither island has fancy restaurants or hotels. I recommend you stay at Auberge Les Petits Saints, as we stayed here and can report that it is perfectly nice and the best on the island (Conde Nast Traveler recommends it, too). The most unusual thing about the Saintes is that its small population (less than 4,000 people) is colorblind (no racial tension). The population is very mixed and it’s not unusual to see green-eyed, pale-skinned black French-speaking locals.

“Terre-de-Haut is known for Pain de Sucre Beach’s coral-rich waters and palm-lined Les Saintes Bay. Overlooking the bay is 19th-century Fort Napoléon, with a museum and cactus garden. Trails cross the volcanic landscape of Terre-de-Bas Island, home to tranquil Grand Anse Beach,” per Wikipedia.

 

• The Grenadines
  • See post to follow soon for the specific islands in the Grenadines!!!!!