11Days10Nights
USD 4,235

Bridgetown - San Juan


Silver Shadow

Cruise Code: SS270120010

Aboard Silver Shadow, sail Bridgetown to San Juan through St. Barts, Bequia and St. Lucia, chasing reefs, beaches and glowing sunsets.

Itinerary
1

Barbados

Bridgetown

Bridgetown, Barbados' UNESCO-listed capital, blends colonial history, rich culture, and white-sand beauty. At The Careenage, pastel buildings overlook the Constitution River, with a plaque marking the city's role in the Transatlantic Slave Trade. Nearby Carlisle Bay offers turquoise water, soft sand, and shipwreck dives with turtles and tropical fish. Explore street food, Broad Street shopping, rum bars on Roebuck Street, and Nidhe Israel Synagogue and museum.
Jan 20, 2027
Departure23:00
2

Saint Vincent And The Grenadines

Bequia

Bequia Island is a rustic, unspoiled Grenadine gem: virgin beaches, quiet bays, rum shacks, and a laid-back feel with only about 6,000 locals. Admiralty Bay is a stunning natural harbor, and tiny Port Elizabeth has a market, turtle sanctuary, and model-ship stalls. Hike Mount Peggy for views, then relax on Princess Margaret Beach or other golden-sand coves. It's a place to slow down, swim, read, and enjoy fresh catch, barbecue, and rum cocktails at beach bars.
Jan 21, 2027
Arrival08:00
Departure18:00
3

Saint Lucia

Castries

St Lucia is a vivid Caribbean island of turquoise seas, green volcanic Pitons, jungle waterfalls, and bright coral reefs. Its beaches and dive spots are rich with colorful fish, while marigot Bay, once a backdrop for Doctor Dolittle, adds cinematic charm. Spot parrots in the palms and dolphins offshore, relax on Vigie Beach, and photograph the dramatic Pitons. In Castries, visit the Cathedral Basilica and the lively market for spices, bananas, and mangos.
Jan 22, 2027
Arrival08:00
Departure18:00
4

Martinique

Trois Ilets

Martinique's Trois Ilets is where French and Caribbean cultures meet. Visit La Pagerie museum for colonial artifacts, including some of Napoleon's love letters, and learn at Savane des Esclaves about Neg Marrons-escaped slaves who survived in the hinterland. The village centers on a church square, with colorful wooden houses and pottery roofs; Josephine was baptized here. It's also prized for beaches like l'Anse à l'Âne, Pointe du Bout, and watersports, plus the Genipa Mangrove.
Jan 23, 2027
Arrival08:00
Departure18:00
5

Dominica

Roseau

Roseau, Dominica's capital on the west coast, blends Caribbean beauty with a strong colonial past. Enjoy volcanic beaches, great snorkeling and diving among coral, marine life and underwater volcanic activity. Explore banana and cocoa plantations, the lively Old Market Square, and the former British fort for sweeping views. Visit the botanical gardens, rainforest waterfalls, and Boiling Lake in Morne Trois Pitons National Park, then relax in hot springs or with a rum punch.
Jan 24, 2027
Arrival08:00
Departure19:00
6

Guadeloupe

Les Saintes

Les Saintes, "Islands of the Saints," is a stunning Caribbean archipelago named by Columbus in 1493. Of nine islands, only two are inhabited. Expect crystal beaches, shallow turquoise seas, lush volcanic cones, rich reefs, kayaking, snorkeling, and catamaran trips. Visit Pain de Sucre Beach and Fort Napoleon, now a cactus park and gardens, and watch for iguanas.
Jan 25, 2027
Arrival08:00
Departure18:00
7

Montserrat

Little Bay, Montserrat

Montserrat is one of the Caribbean's most dramatic islands: relatively undeveloped, with hidden beaches, creeks, and rich natural beauty, and likely an emerging eco-tourism spot. Its history is shaped by volcanic activity, especially the 1995 Soufrière Hills eruption that buried much of the main city, earning it the nickname "Pompeii of the Caribbean." Also called the "emerald isle," it has lush forests, Irish-like coasts, even Guinness-and beautiful Little Bay, the island's future capital.
Jan 26, 2027
Arrival08:00
Departure18:00
8

Saint Kitts And Nevis

St. Kitts

St. Kitts is a lush volcanic island of crystal-clear Caribbean waters, reefs, white-sand beaches, rainforests, and a laid-back "limin" vibe. Explore vine-tangled trails, snorkel or dive with turtles and wrecks, or ride Basseterre's scenic sugar train through unspoiled landscapes. In Basseterre, see the Berkeley Memorial and Independence Square, and visit Brimstone Hill Fortress, the "Gibraltar of the West Indies," a UNESCO World Heritage Site with sweeping coastal views.
Jan 27, 2027
Arrival08:00
Departure19:00
9

Saint Barthelemy

Gustavia, St. Barthelemy

Gustavia, St Barthelemy's capital, is a chic Caribbean harbor town of red roofs, yachts, boutiques, bars, and French flair. From the lighthouse, you can gaze over waters loved by celebrities and divers. The island was first named by Columbus in 1493, later a Swedish colony, and returned to France in 1878; its heritage remains at Fort Karl above Shell Beach. Nearby are shell-strewn shores, turquoise waters, and quiet gems like Colombier Beach-ideal for a sunset rum cocktail.
Jan 28, 2027
Arrival08:00
Departure23:00
10

U.S. Virgin Islands

St John

Like much of the Caribbean, St. John was hit hard by Hurricanes Irma and Maria in 2017, but rebuilding is restoring normality. Small and US-owned since 1917, it was Danish for nearly 250 years before that. Almost two-thirds is protected by Virgin Islands National Park, thanks to Laurence Rockefeller's 1956 gift of 5,000 acres. Its green hills and white beaches remain stunning, and marine life has thrived, with coral reefs, sea turtles, reef sharks and stingrays abundant.
Jan 29, 2027
Arrival08:00
Departure18:00
11

United States

San Juan

Colourful colonial streets, Spanish forts and a lively Caribbean atmosphere make San Juan a captivating cruise stop. Wander the pastel-hued lanes of Old San Juan, savour local flavours and rum, or head beyond the city for golden beaches and lush rainforest scenery. With its blend of history, music and sunshine, this vibrant port offers an unforgettable island welcome.
Jan 30, 2027
Arrival07:00

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