Leeward & Windward Islands Explorer

Leeward & Windward Islands Explorer

Bridgetown, Barbados to Charlotte Amalie, St. Thomas

Feb 2, 2028 to Feb 13, 2028

11 Days

SeaDream I

12806

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.

Date Ports of Call Arrive Depart
Feb 02, 2028 Bridgetown, Barbados,
Barbados
2 PM - 4 PM
(Embarkation)
Overnight
Feb 03, 2028 Bridgetown, Barbados,
Barbados
Early Morning
Feb 03, 2028 Port St. Charles,
Barbados
Morning Evening
Feb 04, 2028 Tobago Cays,
St. Vincent and the Grenadines
Early Morning Afternoon
Feb 04, 2028 Port Elizabeth, Bequia,
St. Vincent and the Grenadines
Afternoon Overnight
Feb 05, 2028 Port Elizabeth, Bequia,
St. Vincent and the Grenadines
Evening
Feb 06, 2028 St. Pierre,
Martinique, F.W.I.
Morning Evening
Feb 07, 2028 Terre De Haut, Îles des Saintes,
Guadeloupe, F.W.I.
Morning Evening
Feb 08, 2028 Charlestown, Nevis,
St. Kitts & Nevis
Morning Afternoon
Feb 08, 2028 South Friars Bay,
St. Kitts & Nevis
Afternoon Late Evening
Feb 09, 2028 Marigot,
Saint Martin, F.W.I.
Morning Afternoon
Feb 09, 2028 Gustavia,
St. Barths, F.W.I.
Afternoon Overnight
Feb 10, 2028 Gustavia,
St. Barths, F.W.I.
Evening
Feb 11, 2028 Spanish Town, Virgin Gorda,
B. V. I.
Morning Morning
Feb 11, 2028 Leverick Bay, Virgin Gorda,
B. V. I.
Morning Late Evening
Feb 12, 2028 White Bay, Jost van Dyke,
B. V. I.
Morning Evening
Feb 13, 2028 Charlotte Amalie, St. Thomas,
U.S.V.I.
Morning 8 AM - 10 AM
(Disembarkation)

Ports

  • Bridgetown, Barbados
    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.

  • Port St. Charles
    Port St. Charles

    Port St. Charles, Barbados, a luxurious marina community nestled on the island’s serene northwest coast (dubbed “The Platinum Coast”), is known to yachting insiders for its calm turquoise waters and powdery, white-sand beaches. This exclusive destination blends natural beauty with refined elegance, offering world-class yachting, upscale villas, and effortless access to vibrant Bajan culture. Your SeaDream yacht drops anchor by the marina, with easy access to waterfront dining and crystal-clear reefs awaiting snorkelers. Just a short stroll south of the marina, Heywoods Beach and Six Men’s Bay await, and slightly north guests will discover smaller, unnamed coves and beaches that are only known to locals—ideal for a private swim or a quiet moment in the sun. The historic town of Holestown, where the first settlers ventured ashore in 1627, invites exploration with its art galleries, exclusive boutiques, and local bistros. Nearby, Farley Hill National Park offers panoramic views and hiking trails through historic ruins and mahogany forests.

  • Tobago Cays
    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.

  • Port Elizabeth, Bequia
    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.

  • St. Pierre
    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.

  • Terre De Haut, Îles des Saintes
    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.

  • Charlestown, Nevis
    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.

  • South Friars Bay
    South Friars Bay

    South Friar's Bay offers SeaDream guests a new way to explore the island of St. Kitts. Rather than docking at the capital, the yacht will be anchored in the bay. This particular bay is one of the two bays stretching along the coast of the isthmus connecting the Southeast Peninsula, with the rest of the island of Saint Kitts. From swimming and snorkeling on the south side to body surfing on the north, Friar's Bay offers guests several options. Many locals consider the southern beach the best on the island. If you are thirsty, no worries as there are multiple beach bars, offering various food and beverage options. The island itself offers several land adventure options including the Unesco Awarded Brimstone Fortress, Zip Lines, off road adventures and golf at the Royal St. Kitts.

  • Marigot
    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.

  • Gustavia
    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.

  • Spanish Town, Virgin Gorda
    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.

  • Leverick Bay, Virgin Gorda
    Leverick Bay, Virgin Gorda

    Enjoy the welcoming Caribbean breeze and the famous Baths located nearby. Other attractions include the Coppermine Ruins and Gorda Peak National Park. Of course, snorkeling is popular as are the sandy white beaches.

  • White Bay, Jost van Dyke
    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!

  • Charlotte Amalie, St. Thomas
    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.


Suites & Staterooms

*Single Supplement for this voyage is 175% for Yacht Club Deck 2, 3 and 4. For Commodore, Admiral and Owners Suite, a 200% single supplement rate applies.


Government, Port, Document Issuance, Handling & Service fees: $660 per guest (included)


Please Note: Fares are capacity controlled and may change without notice. The fares are per person based on double occupancy. Single and third person rates are also available. SeaDream Yacht Club strongly recommends that all guests purchase travel insurance.


Yachting Land Adventures & Activities

    Please check back soon for updates.


Testimonials

Exceeded my expectations. Outstanding food and exceptional service from a top notch crew that truly cares about their guests! Mr & Mrs WrightPA
Another great trip with SeaDream. We so enjoyed the service & attention to detail. Sara J.California