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Leeward & Windward Islands Explorer

Summary

Volcanic silhouettes, secluded palm-lined beaches, and unassuming island charm define your yachting journey through the British Virgin Islands, French West Indies, Guadeloupe, and the Grenadines. Sailing from Barbados, call on St. John’s sheltered Cruz Bay, for snorkeling and diving spots off perfectly manicured beaches. Discover Spanish Town, your gateway to The Baths, Virgin Gorda’s geologic wonder made of awe-inspiring boulders that form sheltered sea pools on the beach’s edge. Take in Tobago Cays, as SeaDream drops anchor in a heavenly lagoon. Overnight in Bequia, a tiny island of quiet lagoons, reefs, and silvery stretches of beach, often referred to as “the best-kept secret” of the Caribbean. Explore Martinique when your yacht calls on St. Pierre, nestled at the foot of Mount Pelée on the island’s lush northwest coast; Îles des Saintes, a small archipelago of eight incredible islands off the southern coast of Guadeloupe; and the verdant mountainous landscape of Nevis. See the isle of St. Kitts through the eyes of South Friars Bay, stretching along the isthmus coast of the island’s southeast peninsula. Call on St. Martin’s French-spirited town of Marigot, where candy-colored houses and neighboring cafés, bistros, and luxury boutiques welcome you. Overnight in chic St. Barths, the jetsetter’s Caribbean playground, radiating the ambiance of the South of France with a distinct island flair. Discover Spanish Town, your gateway to The Baths, Virgin Gorda’s geologic wonder made of awe-inspiring boulders that form sheltered sea pools on the beach’s edge, and Leverick Bay, kissing Virgin Gorda’s northern coast. Relax on the barefoot island of Jost van Dyke, home to our signature Champagne & Caviar Splash®, before disembarking in lovely Charlotte Amalie, St. Thomas, where you may choose to explore more.

Cruise line SeaDream Yacht Club

Ship SeaDream I

Duration 11 nights

Type Ocean Cruise

Regions Caribbean,
Americas,
South America

Itinerary & Map

Bridgetown → Charlotte Amalie 12 days · 12 ports · 0 sea days
Day 1 Bridgetown Embark

Located beside the island’s only natural harbour, the capital of Barbados combines modern and colonial architecture with glorious palm tree-lined beaches and a...

Full description
Day 2 Bridgetown and Port St Charles

Located beside the island’s only natural harbour, the capital of Barbados combines modern and colonial architecture with glorious palm tree-lined beaches and a...

Full description
Day 3 Tobago Cays and Port Elizabeth, Bequia

The Tobago Cays are an archipelago located in the Southern Grenadines of Saint Vincent and the Grenadines comprising five small islands and extensive coral reef...

Full description
Day 4 Port Elizabeth, Bequia

Bequia is a Carib word meaning "island of the cloud." Hilly and green with several golden-sand beaches, Bequia is 9 miles (14½ km) south of St. Vincent's southw...

Full description
Day 5 Saint Pierre
Day 6 Terre-de-Haut
Day 7 Charlestown and South Friars Bay
Day 8 Marigot and Gustavia

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a m...

Full description
Day 9 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 10 Spanish Town, Virgin Gorda and Leverick Bay, Virgin Gorda

Virgin Gorda, or "Fat Virgin," received its name from Christopher Columbus. The explorer envisioned the island as a pregnant woman in a languid recline, with Go...

Full description
Day 11 White Bay, Jost Van Dyke
Day 12 Charlotte Amalie Disembark
Scroll for all 12 days
Route overview map
Day 1 Bridgetown Embark

Located beside the island’s only natural harbour, the capital of Barbados combines modern and colonial architecture with glorious palm tree-lined beaches and a...

Full description
Day 2 Bridgetown and Port St Charles

Located beside the island’s only natural harbour, the capital of Barbados combines modern and colonial architecture with glorious palm tree-lined beaches and a...

Full description
Day 3 Tobago Cays and Port Elizabeth, Bequia

The Tobago Cays are an archipelago located in the Southern Grenadines of Saint Vincent and the Grenadines comprising five small islands and extensive coral reef...

Full description
Day 4 Port Elizabeth, Bequia

Bequia is a Carib word meaning "island of the cloud." Hilly and green with several golden-sand beaches, Bequia is 9 miles (14½ km) south of St. Vincent's southw...

Full description
Day 5 Saint Pierre
Day 6 Terre-de-Haut
Day 7 Charlestown and South Friars Bay
Day 8 Marigot and Gustavia

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a m...

Full description
Day 9 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 10 Spanish Town, Virgin Gorda and Leverick Bay, Virgin Gorda

Virgin Gorda, or "Fat Virgin," received its name from Christopher Columbus. The explorer envisioned the island as a pregnant woman in a languid recline, with Go...

Full description
Day 11 White Bay, Jost Van Dyke
Day 12 Charlotte Amalie Disembark

Bridgetown

Located beside the island’s only natural harbour, the capital of Barbados combines modern and colonial architecture with glorious palm tree-lined beaches and a number of historical attractions. Experience the relaxed culture of the city renowned for its British-style parliament buildings and vibrant beach life, and seek out the Anglican church and the 19th-century Barbados Garrison. The distance between the ship and your tour vehicle may vary. This distance is not included in the excursion grades.

Tobago Cays and Port Elizabeth, Bequia

The Tobago Cays are an archipelago located in the Southern Grenadines of Saint Vincent and the Grenadines comprising five small islands and extensive coral reefs. The cays – Petit Rameau, Petit Bateau, Baradal, Petit Tabac and Jamesby – are a popular tourism destination.

Port Elizabeth, Bequia

Bequia is a Carib word meaning "island of the cloud." Hilly and green with several golden-sand beaches, Bequia is 9 miles (14½ km) south of St. Vincent's southwestern shore; with a population of 5,000, it's the largest of the Grenadines. Although boatbuilding, whaling, and fishing have been the predominant industries here for generations, sailing has now become almost synonymous with Bequia. Admiralty Bay is a favored anchorage for both privately owned and chartered yachts. Lodgings range from comfortable resorts and villas to cozy West Indian—style inns. Bequia's airport and the frequent ferry service from St. Vincent make this a favorite destination for day-trippers, as well. The ferry docks in Port Elizabeth, a tiny town with waterfront bars, restaurants, and shops where you can buy handmade souvenirs—including the exquisitely detailed model sailboats that are a famous Bequia export. The Easter Regatta is held during the four-day Easter weekend, when revelers gather to watch boat races and celebrate the island's seafaring traditions with food, music, dancing, and competitive games.To see the views, villages, beaches, and boatbuilding sites around Bequia, hire a taxi at the jetty in Port Elizabeth. Several usually line up under the almond trees to meet each ferry from St. Vincent.

Marigot and Gustavia

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a more genteel ambience, more fashionable shopping, and a Continental flair. The Dutch tends to be less expensive, has casino hotels, and more nightlife. Water sports abound all over—diving, snorkeling, sailing, and windsurfing are all top draws. And it's easy to while away the day relaxing on one of the 37 beaches, strolling the boardwalk of Dutch-side Philipsburg, and exploring the very French town of Marigot. Although luck is an important commodity at St. Maarten's 13 casinos, chance plays no part in finding a good meal at the island’s excellent eateries. The best way to explore St. Maarten/St. Martin is by car. Though often congested, especially around Philipsburg and Marigot, the roads are fairly good, though narrow and winding, with some speed bumps, potholes, roundabouts, and an occasional wandering goat herd. Few roads are marked with their names, but destination signs are common. Besides, the island is so small that it's hard to get really lost—at least that is what locals tell you. If you’re spending a few days, get to know the area with a scenic "loop" around the island. Be sure to pack a towel and some water shoes, a hat, sunglasses, and sunblock. Head up the east shoreline from Philipsburg, and follow the signs to Dawn Beach and Oyster Pond. The road winds past soaring hills, turquoise waters, quaint West Indian houses, and wonderful views of St. Barth. As you cross over to the French side, turn into Le Galion for a stop at the calm sheltered beach, the stables, the butterflies, or the windsurfing school, then keep following the road toward Orient Bay, the St-Tropez of the Caribbean. Continue to Anse Marcel, Grand Case, Marigot, and Sandy Ground. From Marigot, the flat island of Anguilla is visible. Completing the loop brings you past Cupecoy Beach, through Maho and Simpson Bay, where Saba looms in the horizon, and back over the mountain road into Philipsburg.

Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

Spanish Town, Virgin Gorda and Leverick Bay, Virgin Gorda

Virgin Gorda, or "Fat Virgin," received its name from Christopher Columbus. The explorer envisioned the island as a pregnant woman in a languid recline, with Gorda Peak being her belly and the boulders of the Baths as her toes. Different in topography from Tortola, with an arid landscape covered with scrub brush and cactus, the pace of life is slower here, too. Goats and cattle own the right of way, and the unpretentious friendliness of the people is winning. The top sight (and beach for that matter) is the Baths, which draws scores of cruise-ship passengers and day-trippers to its giant boulders and grottoes that form a perfect snorkeling environment.

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Wed 2 Feb 2028
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