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With so many alluring ports of call at your disposal, planning an extended West Indian cruising itinerary can seem intimidating. The relatively close proximity of the islands that comprise the Windward and Leeward island chains of the Caribbean makes the region well situated for island-hopping. For example, you can go from snorkeling off Anguilla one day to enjoying French cuisine on St. Barts the next.

We asked dozens of experienced cruisers about their favorite Caribbean destinations. From iconic, paradisiacal backdrops to far-flung secret anchorages, here’s the Passagemaker-​­approved 2019 Caribbean wanderlist.

St. Lucia


Few Caribbean islands are as photogenic as St. Lucia, where the towering Pitons, a jagged pair of volcanic peaks, are instantly recognizable. Ashore, the island offers golden-sand beaches, prized hiking trails and rainforest excursions. Lively reefs are just offshore. Marigot Bay is one of the most idyllic protected harbors in the Caribbean, with dense, forested hills surrounding three sides. Situated on the more favorable southwestern end of the island, the Pitons create a dramatic backdrop for anchorage.

The Exumas


The 365 vibrant islands and tiny cays of the Exumas might just be the inspiration for Jimmy Buffett’s song “One Particular Harbor.” It’s pure paradise with turquoise waters as gin-clear as any on the planet. Quite a contrast from the more touristy parts of the Bahamas, in the Exumas you’ll often have the beaches all to yourself—except at Big Major Cay, where resident pigs swim out to greet you. Don’t miss Thunderball Grotto, named for the James Bond movie “Thunderball,” where inside, placid water teems with a kaleidoscope of brilliantly colored fish.

Turks & Caicos

If you’re into diving or snorkeling, it’s hard to do better than Turks and Caicos, an archipelago of 40 low-lying coral islands southeast of the Bahamas. The gateway island of Providenciales, known as Provo, is home to expansive Grace Bay Beach, with resorts, shops and restaurants. Dive sites include a 14-mile barrier reef on Provo’s north shore and a dramatic 7,000-foot underwater wall off Grand Turk Island.

St. Kitts and Nevis 


This dual-island nation near the top of the Leeward Islands is known for its striking mountains and isolated beaches. The larger of the two islands, St. Kitts, is dominated by the dormant Mount Liamuiga volcano, home to a crater lake, green vervet monkeys and a rainforest with hiking trails.



Rising majestically from the azure waters of the Leeward Islands, Saba (to the south of St. Martin) boasts an “old Caribbean” feel: safe, friendly and charming, above and below the waterline. Surrounded by a marine park and renowned for diving, Saba’s waters are home to sea turtles, sharks and underwater mountains. The approach is breathtaking, with the island’s dormant volcano, Mount Scenery, rising as you get closer. Hiking ashore is just as memorable. The village has “gingerbread houses” with well-kept flower gardens.

Iles Des Saintes


Formed by nine unspoiled islands, two of which are inhabited, Îles des Saintes (or “les Saintes”) may feel even more French than St. Barts. The archipelago’s main island, Terre-de-Haut, with its bistro-lined streets, offers French and Creole culinary delights such as the traditional tourment d’amour cake—a crusty-edged, soft-centered tart flavored with guava, pineapple or coconut. 



Having undergone recent development, Canouan, an approximately 5-square-mile island in the middle of St. Vincent and the Grenadines, has emerged as a budding Caribbean hot spot, with sleepy rural charm, incredible beaches and nature walks. Glossy Bay Marina, at the southern end, opened to yachts in 2017. Charlestown Bay and Rameau Bay are the main anchorages on the western (leeward) side of the island, where locals will come by selling fish, lobster, bread, ice, water and diesel. As with most places in the islands, if you’re taking on diesel, be sure to filter it first.  



This large, diverse island at the southern end of the Caribbean Sea has a lot to offer. Cruisers who want to explore ashore for a few days can hike to the waterfalls in Grand Etang National Park, tour a chocolate factory, see parrots and monkeys in the rainforest, and shop for nutmeg and other spices in bustling St. George’s market.



When seen from overhead, the topographically diverse French island of Guadeloupe is shaped like a butterfly. Anchor on the northern end of the island in the sheltered bay just off Deshaies, a fishing village dotted with local eateries and bars. Visit a wild tropical river and a botanical garden. Nearby is Pigeon Island, where the main attraction is the underwater Cousteau Reserve, prime grounds for diving and snorkeling.


While celebrities go to St. Barts to be seen, they go to Anguilla for privacy. This British territory has gin-clear water that rings magnificent, secluded beaches. Sandy Island, Anguilla, is an oasis of greenery and palm trees where a beach barbecue can be great fun. Save time for the uninhabited Prickly Pear Cays, islets great for snorkeling along a coral reef. Scilly Cay is a tiny island in the fishing village of Island Harbour on the eastern tip of Anguilla with a great beach bar and tables in the sand. The cooks will prepare your catch any way you like. 

St. Barts


St. Barts is the “it island” for fans of the Saint-Tropez lifestyle. There is a hint of Sweden here, too: The French island’s capital, Gustavia, is named for the Swedish King Gustav III, because the island was a Swedish colony starting in 1784. Many of the street names are still Swedish. Even still, you’ll find plenty of French rosé served during lunches at Nikki Beach and La Plage restaurant, where a midday meal can go on for hours and blend into dinnertime.



Antigua, the largest of the English-speaking Leeward islands, is where Admiral Horatio Nelson was stationed during the 1780s. The historic naval base—Nelson’s Dockyard at English Harbour—offers a national museum with restored officers’ quarters, capstans and artifacts from Nelson’s era. Don’t miss the epic sunset celebration with sweeping views at Shirley Heights. Beyond its candy-colored villages and warm locals, Antigua also offers lively, rum-infused nightlife.