Windward & Leeward Islands

From $8,418 per person

8 days

Ship: SeaDream II

Windward & Leeward Islands
SeaDream Yacht Club

The British Virgin Islands, Netherlands Antilles, and French West Indies meld into the dreamiest of island journeys, complete with the most breathtakingly diverse spots in the Caribbean. Sailing from San Juan, begin in Jost van Dyke’s sheltered White Bay, home to our signature Champagne & Caviar Splash®. Unveil the Caribbean’s hidden treasure, a small island discovered in the 1700s named Sint Eustatius, tucked away in the Netherlands Antilles. Overnight in chic St. Barths, the jetsetter’s Caribbean playground, where luxe boutiques, sidewalk cafés, and sun-kissed beaches welcome you. Discover Antigua’s culturally rich Falmouth Bay, a short stroll from Nelson's Dockyard and the English Harbour. Explore Îles des Saintes, a small archipelago of eight islands off the southern coast of Guadeloupe, home to secluded beaches and coral-rich reefs brimming with marine life. Take in Martinique’s French-infused Le Marin, offering the quiet beaches of Plage des Pointe Marin and Plage des Salines. Your journey concludes in Bridgetown, where you may choose to explore more of Barbados’ colonial capital.

Journey Summary

  • Day 1 - Jan. 25, 2026, Sun. - San Juan
  • Day 2 - Jan. 26, 2026, Mon. - White Bay, Jost van Dyke
  • Day 3 - Jan. 27, 2026, Tue. - Sint Eustatius
  • Day 4 - Jan. 28, 2026, Wed. - Gustavia
  • Day 5 - Jan. 29, 2026, Thu. - Falmouth Bay
  • Day 6 - Jan. 30, 2026, Fri. - Terre De Haut, Îles des Saintes
  • Day 7 - Jan. 31, 2026, Sat. - Le Marin
  • Day 8 - Feb. 1, 2026, Sun. - Bridgetown, Barbados

Detailed Itinerary

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

Day 1 - January 25, 2026

San Juan

San Juan, founded in the 1520’s by Spanish settlers, is both the largest city and the capital city of Puerto Rico. A territory of the Unites States, Puerto Rico is comprised of the large main island as well as five smaller islands, including the popular islands of Vieques and Culebra (both ports of call on select SeaDream voyages).

SeaDream docks in Old San Juan, the oldest part of the city. Parts of this historic port city are still surrounded by stone walls dating back to the 1500’s. Narrow cobblestone streets, small shops, and points of interest like Cathedral of San Juan Bautista make this charming city a great place to stroll. Guests sailing into or departing from San Juan will enjoy views of Castillo de San Felipe del Morro, a mid- 1700’s Spanish fortress.

San Juan Luiz Munoz Marin Airport is approximately a 30-minute drive to the port in Old San Juan. Currency in Puerto Rico is USD.

Day 2 - January 26, 2026

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 3 - January 27, 2026

Sint Eustatius

Unveil the Caribbean’s hidden treasure, a small island discovered in the 1700s named Sint Eustatius. Originally a trading hub for sugar and cotton, the island has now become a must-see landscape. This castaway-like frontier hosts a range of natural jewels including dazzling reefs, brimming marine life, and historical wrecks of the island’s capital, Oranjestad, which is now mostly submerged.

Day 4 - January 28, 2026

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 5 - January 29, 2026

Falmouth Bay

Falmouth Bay is a short walk from Nelson's Dockyard and the English Harbour. Historic buildings and mills surround it. This harbor and the quiet village has plenty of shops, restaurants and the yacht club. Historic sites, tasty cuisine and a lively cultural scene can all be found on Antigua. But most often it's the beauty and versatility of the island's 365 beaches that draw travelers from afar. Land Adventure possibilities include a helicopter ride over Montserrat, a jeep and snorkel safari and a St. John’s City and shopping exploration.

Day 6 - January 30, 2026

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 - January 31, 2026

Le Marin

Sea life, sun, picturesque views, and fine restaurants make up this city in Martinique. The island is a French Territory, and the marinas in Le Marin are frequented by charter yachts and large sailboats. European influence is evident in this city’s architecture and style.

Day 8 - February 01, 2026

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.

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Jan 25, 2026

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