Leeward & Windward Islands Explorer

From $12,658 per person

12 days

Ship: SeaDream I

Map of Caribbean islands, highlighting destinations for the Leeward & Windward Islands Explorer sailing itinerary.
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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.

Journey Summary

  • Day 1 - Feb. 2, 2028, Wed. - Bridgetown, Barbados
  • Day 2 - Feb. 3, 2028, Thu. - Bridgetown, Barbados
  • Day 3 - Feb. 4, 2028, Fri. - Tobago Cays
  • Day 4 - Feb. 5, 2028, Sat. - Port Elizabeth, Bequia
  • Day 5 - Feb. 6, 2028, Sun. - St. Pierre
  • Day 6 - Feb. 7, 2028, Mon. - Terre De Haut, Îles des Saintes
  • Day 7 - Feb. 8, 2028, Tue. - Charlestown, Nevis
  • Day 8 - Feb. 9, 2028, Wed. - Marigot
  • Day 9 - Feb. 10, 2028, Thu. - Gustavia
  • Day 10 - Feb. 11, 2028, Fri. - Spanish Town, Virgin Gorda
  • Day 11 - Feb. 12, 2028, Sat. - White Bay, Jost van Dyke
  • Day 12 - Feb. 13, 2028, Sun. - Charlotte Amalie, St. Thomas

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - February 02, 2028

Bridgetown, Barbados

SeaDream uses the port of Bridgetown as the hub for their Southern Caribbean voyages as well as some voyages that cross the Atlantic. The Island itself includes UNESCO Heritage Sites, excellent beaches and history dating back to 1628. The climate is tropical with constant warm temperatures during the year cooled by light trade winds.

Day 2 - February 03, 2028

Bridgetown, Barbados

SeaDream uses the port of Bridgetown as the hub for their Southern Caribbean voyages as well as some voyages that cross the Atlantic. The Island itself includes UNESCO Heritage Sites, excellent beaches and history dating back to 1628. The climate is tropical with constant warm temperatures during the year cooled by light trade winds.

Day 3 - February 04, 2028

Tobago Cays

Imagine an intimate cluster of five uninhabited islands, heavenly lagoons full of green turtles, coral reefs, colorful fish and crystal clear waters. This is the setting when SeaDream anchors off the Tobago Cays. Zodiacs will whisk guests from the marina to the beautiful beach. There may be some locals selling crafts so remember to bring some dollars. This is an idyllic yachting anchorage, a dream for scuba divers, a paradise for beachcombers, and a film location for the Pirates of the Caribbean, the Tobago Cays and the Tobago Cays Marine Park is one of the world’s most awe inspiring island destinations.

Day 4 - February 05, 2028

Port Elizabeth, Bequia

Bequia is the northernmost and largest of the Grenadines, just seven square miles of quiet lagoons, reefs, and long silvery stretches of beach. Among the first things you will notice are the colorful model boats set up on stands around the tiny harbor, representing the island's maritime history. If you are lucky enough to have a late call, don’t miss Mac’s Lobster Pizza.

Day 5 - February 06, 2028

St. Pierre

St. Pierre, Martinique, nestled at the foot of Mount Pelée on the island’s lush northwest coast, is a captivating blend of natural beauty and rich history—perfect for culture lovers, history buffs, and those seeking an off-the-beaten-path escape. Once dubbed the “Paris of the Caribbean,” and “City of Art and History,” this seaside town offers a unique mix of French-Creole charm and dramatic volcanic legacy. Explore the open-air ruins left by the 1902 eruption, visit science museums and the prestigious Depaz & Neisson rum distillery, and stroll cobblestone streets lined with colonial remnants and vibrant local markets. Just offshore, divers can explore historic shipwrecks resting beneath turquoise waters, while nearby black-sand beaches and rainforest trails offer moments of quiet seclusion. Your yacht drops anchor just steps away from town, with easy access to Martinique’s many charms.

Day 6 - February 07, 2028

Terre De Haut, Îles des Saintes

If you’re looking for a small part of France in the heart of Guadeloupe, Terre de Haut is your go-to. Being the largest of the eight small islands that make up Les Saintes, Terre de Haut is a charming and scenic village rich with red-roofed houses and accompanying gardens of flourishing Hibiscus. Known for its robust reefs and great underwater visibility, Terre de Haut has also become a favorite among divers.

Day 7 - February 08, 2028

Charlestown, Nevis

Nevis is one of our favorite islands, and we encourage you to explore Nevis beyond the small town to make the most of your visit! We offer several excellent and varied options for you to do so and still leave you with plenty of time on your own for the beach. Less commercial and laidback than its large neighbor St. Kitts, Nevis, at first glimpse, offers a stunning approach with dramatic views of the potentially active volcanic Nevis Peak (3,232 feet/985 meters). Your SeaDream tender will bring you within a few steps of the small town center. Charlestown does not offer too many sightseeing or shopping opportunities though the house where American statesman Alexander Hamilton was born is only a short walk away along the waterfront (now the Museum of Nevis History). To enjoy Nevis to its full potential, we recommend that you divide your day into Morning, Lunch/Afternoon and Evening activities.

Morning - Start your day by exploring the island, above or under water, on one of our fun optional Land Adventures. They are all enjoyable & exciting, and you will also support the local community. The Four Seasons Resort still offers incredible golf options as well as beautiful beach and dining facilities. Another option for lunch is the L'Escale French Caribbean-style bistro, just down the road near the Oualie Pier.

Evening - For a romantic sunset with cocktails and a snack or dinner, we like to take the short drive to see Gillian, the owner of the charming Bananas Restaurant, which offers lovely views surrounded by lush tropical gardens. Of course, there is also Sunshine's Beach Bar & Grill, home of the famous "Killer Bee" Caribbean rum drink. We hope that the above recommendations allow you to plan your special day on Nevis. Now, all you have to do is to decide which of the optional morning activities to join.

Day 8 - February 09, 2028

Marigot

Marigot is the main town and capital on the French side of Saint Martin. The city of Marigot is perhaps the most French in spirit of all the cities in the Caribbean. Colonial houses stand beside cafés and bistros, pastry shops and luxury boutiques, and in many ways, it looks just like any of the French market towns you might expect to find in Europe. At the southern end of town by the harbor is Marina Port la Royale. This area includes elegant stores with the latest in European designer fashion and fine jewelry, all duty and tax-free. The entire city is only four streets wide, so it is very easy to get around. Marigot was named the capital during the reign of King Louis XVI, who built Fort St. Louis on a hill near Marigot Bay. Today, that building is the most important in the city. SeaDream anchors off Marigot and offers several yachting land adventures as well as the possibility to play with the toys at the marina.

Day 9 - February 10, 2028

Gustavia

Perhaps our most treasured destination in the Caribbean! This small island belonging to the French West Indies has so much to offer our SeaDream guests. Incredible shopping only steps away from the pier. Incredible beaches, resorts, restaurants and activities both day and night. SeaDream has created various land adventures for you to discover the island from sea or land. Ask one of the officers to take you on a hike or bike ride around the island. Another great activity here is to simply relax and watch all of the incredible yachts arriving and departing just off your SeaDream yacht.

Day 10 - February 11, 2028

Spanish Town, Virgin Gorda

Nearly every publication written about Virgin Gorda will emphasize the need to visit “The Baths” – don’t miss it! SeaDream generally arrives early and anchors off Spanish Town to give guests an early start to view The Baths before all of the tourists arrive from the neighboring Islands. You may also consider excellent scuba diving options or an opportunity to swim with the dolphins. SeaDream navigates scenically up the coast and arrives in North Sound to anchor just off the Bitter End Yacht Club. Here we offer watersports, land adventures, hiking options with the crew and tenders to the Bitter End! Depending on the voyage, you may also visit Prickly Pear Island for another signature Champagne & Caviar Splash® option with an incredible setting.

Day 11 - February 12, 2028

White Bay, Jost van Dyke

The BVI’s barefoot island and home of the "Painkiller" drink. Population depends on the month – typically 250-300. This is another SeaDream destination where you may be served Champagne & Caviar Splash® followed by a beach barbecue lunch. A hike is always offered to guests to visit the famous Foxy’s Bar at Great Harbour (hopefully, the boutique is open) or you can stroll a few meters down the beach to the Soggy Dollar Bar. Snorkeling equipment is provided as well as some of our water toys!

Day 12 - February 13, 2028

Charlotte Amalie, St. Thomas

The capital and largest city in the U.S. Virgin Islands. It has two ports of call for cruise vessels, Havensight and Crown Bay. SeaDream yachts are almost always docked at Crown Bay which is very close to the airport. In the event the yachts call to the island as a port of call rather than an embarkation point, you will find the yacht anchored in the bay and tendering downtown. The island has tons of history, beautiful beaches, a fantastic golf course and incredible shopping options.

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Feb 02, 2028

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SeaDream I anchored in vibrant blue waters, showcasing its luxurious design and elegant amenities for an exclusive cruise.
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