Windward Islands Explorer

From $8,418 per person

8 days

Ship: SeaDream II

Map highlighting the Windward Islands in the Caribbean, including various locations marked for exploration.
SeaDream Yacht Club logo

Journey Summary

  • Day 1 - Feb. 22, 2026, Sun. - Bridgetown, Barbados
  • Day 2 - Feb. 23, 2026, Mon. - Port Elizabeth, Bequia
  • Day 3 - Feb. 24, 2026, Tue. - Mayreau
  • Day 4 - Feb. 25, 2026, Wed. - Rodney Bay
  • Day 5 - Feb. 26, 2026, Thu. - Le Marin
  • Day 6 - Feb. 27, 2026, Fri. - Terre De Haut, Îles des Saintes
  • Day 7 - Feb. 28, 2026, Sat. - Falmouth Bay
  • Day 8 - Mar. 1, 2026, Sun. - Philipsburg

Detailed Itinerary

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

Day 1 - February 22, 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.

Day 2 - February 23, 2026

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 3 - February 24, 2026

Mayreau

Accessible only by yacht and small sailboats, Mayreau is the smallest public island of the Grenadines, with an area of about .46 square miles and a population of less than 300, centered in an unnamed village on a hilltop in the southwest of the island—its highest point and a nice hike from Saline Beach, where SeaDream anchors. Surrounded by magnificent coral reefs and gorgeous beaches, Mayreau and its surrounding Tobago Cays waters sit in a nationally protected area that has experienced a resurgence of marine life, including turtles that swim and feed while you mingle with and observe them. Take in the flora and fauna and don’t miss some of the best snorkeling in the world. Perhaps the ideal spot to anchor, Saline Bay provides easy access to Saline Bay Beach and Salt Whistle Bay Beach, a rare double-sided beach.

Day 4 - February 25, 2026

Rodney Bay

Rodney Bay is a bay on the North West coast of Saint Lucia; it is along the northwestern coast of the island to the north of Choc Bay. It is named after British naval officer George Brydges Rodney. We will anchor and offer tender service to one of the local bars or direct to the marina. Guests can enjoy the Yachting Land Adventures, water sports, the local beaches or a hike to Pigeon Island.

Day 5 - February 26, 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 6 - February 27, 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 - February 28, 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 8 - March 01, 2026

Philipsburg

Philipsburg is the main town on the Dutch side of St. Maarten. The town is situated on a narrow stretch of land between Great Bay and the Great Salt Pond. Philipsburg was founded in 1763 by John Philips, a Scottish captain in the Dutch navy. The settlement soon became a center for international trade. The main shopping district is located on Front Street and is in the heart of the city. Many consider Philipsburg to be the best shopping opportunity in the Caribbean. Depending on the traffic, SeaDream has the option to anchor or dock alongside. One of the highlight activities may be to participate in the America’s Cup 12 Metre Regatta.

Dates and Prices

Select year & month:

Unavailable dates are greyed out

JanFebMarAprMayJunJulAugSepOctNovDec

Available dates:

Feb 22, 2026

Ship

Your cruise ship

SeaDream II sails gracefully on calm waters under a clear blue sky, showcasing luxury and elegance.
SeaDream Yacht Club logo

consultation

Need information to make a decision?

Reach out to our travel concierges today to create your perfect journey.