Pearls of the Caribbean

Fort-de-France Roundtrip - 8 Day Itinerary aboard Le Bougainville

Wander at Fort-de-France Harbor
Discover Union Island Beaches
Snorkel at Tobago Cays Reefs
Swim Pompierre Beach Les Saintes

Starts / Ends: Fort de France / Fort de France
Activity Level: Variable

Embark on an 8-day Caribbean cruise from Martinique through the Grenadines aboard Le Bougainville. Explore vibrant towns, secluded beaches, coral reefs, tropical islands, and volcanic landscapes. Snorkel, swim, stroll along scenic shores, and enjoy historic sites.

Cruise Details

Lush green forests and clear blue waters of the Caribbean

from $5,000

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San Juan to San Juan

San Juan Roundtrip - 8 Day Itinerary aboard Silver Dawn

Snorkel Trunk Bay reefs in St John
Witness Gustavia harbor views
Ride horses along Antigua beaches
Enjoy swimming at Jost Van Dyke

Starts / Ends: San Juan / San Juan
Activities: Wildlife Viewing, Local Market Visits, Kayaking, Rainforest Exploration, Archaeological Site Visits, Hiking
Activity Level: Variable

Depart from San Juan and explore Caribbean islands on an 8-day cruise aboard Silver Dawn. Visit St John, Gustavia, Antigua, Martinique, St Kitts, and Jost Van Dyke. Swim in clear waters, snorkel vibrant reefs, hike rainforest trails, and relax on white sand beaches. Discover a mix of nature, culture, and coastal views.

Cruise Details

from $2,080

SS 25%

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Grenadine Islands

8 Day Itinerary aboard Royal Clipper

Visit one island in Grenadines
Smell the aroma of Grenada
Walk and swim at Marigot Bay
Taste the spicy Creole cooking

Starts / Ends: Bridgetown / Bridgetown
Activity Level: Variable

On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.

Cruise Details

View of Mount Pelée overlooking Saint-Pierre, northwest Martinique, French Caribbean island

from $6,995

EBD 30%

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Sun-Drenched Sailing Days

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit

Explore Philipsburg beaches
Visit Saint-Pierre ruins
Uncover St. Lucia’s Pitons
Discover Dominica’s jungle

Starts / Ends: Philipsburg / Philipsburg
Activity Level: Variable

Sail 8 days aboard Sea Cloud Spirit through the Caribbean, Lesser Antilles & Grenadines. You explore St. Maarten, Martinique, St. Lucia, Dominica, Nevis, and Anguilla, combining colonial towns, volcanic peaks, rainforests, and white-sand beaches with authentic sailing experiences at sea.

Cruise Details

from $6,495

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Relax The Caribbean Way

Roundtrip Bridgetown - 8 Day Itinerary aboard Sea Cloud II

Snorkel in the Tobago Cays
Discover Grenada’s spices
Explore Saint-Pierre, Martinique
View Gros and Petit Piton

Starts / Ends: Bridgetown / Bridgetown
Activities: Small Ship Sailing, Snorkeling, Stand Up Paddle Boarding
Activity Level: Variable

Experience an 8-day voyage aboard Sea Cloud II roundtrip from Bridgetown, Barbados, through the Lesser Antilles & Grenadines. You snorkel in the Tobago Cays, explore spice-rich Grenada, visit Saint-Pierre in Martinique, admire St. Lucia’s Pitons, and enjoy Caribbean sunsets at sea.

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Magnificent sailing ship moored in the Soufrière Bay, on the southwest coast of Saint Lucia.

from $2,010

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Grenada to Antigua

St George - St John - 8 Day Itinerary aboard Star Clipper

Tour St. George's Fort George
Visit Bequia Port Elizabeth
Snorkel Tobago Cays
Relax on Martinique turquoise water

Starts / Ends: St. Georges / St. John's
Activity Level: Variable

Embark on an 8-day cruise from St. George’s, Grenada, aboard the Star Clipper, visiting highlights like Fort George and the Tobago Cays for snorkeling. The journey wraps up in St. Kitts after exploring St. Lucia's Pitons, Martinique's beaches, and Dominica's rainforests.

Cruise Details

from $2,010

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

Explore St. John's dockyards
Tour Basseterre colonial history
Hike St. Kitts rainforests
Swim South Friars Bay waters

Starts / Ends: St. John's / St. John's
Activity Level: Variable

Join an 8-day Caribbean cruise from St. John's, Antigua, on the Star Clipper, exploring destinations like St. Barts, St. Kitts, and Martinique. Experience snorkeling, historic tours, and diverse beaches while enjoying the beauty of the French and British West Indies.

Island Odyssey: Bahamas to the Grenadine

Nassau - Bridgetown - 11 Day Itinerary aboard Scenic Eclipse

Explore Nassau’s vibrant capital
Visit Staniel Cay’s beaches
Discover San Salvador’s coral reefs
Stroll St. Barts iconic Shell Beach

Starts / Ends: Nassau / Bridgetown
Activities: Helicopter Tours
Activity Level: Variable

Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.

Cruise Details

from $2,080

SS 25%

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Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper

Explore beaches in Barbados
See lush island of St. Lucia
Discover Falmouth Harbour, Antigua
Visit sophisticated Martinique

Starts / Ends: Bridgetown / Bridgetown
Activity Level: Variable

Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.

Cruise Details

St. George's, Grenada's charming capital city known for having the most beautiful harbor in the Caribbean.

from $3,150

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Grenada Roundtrip

Roundtrip St George - 12 Day Itinerary aboard Star Clipper

Tour St. George's Sendall Tunnel
Taste Castara Bay Tobago's Creole
Stroll Admiralty Bay waterfront
View Saint Pierre colonial ruins

Starts / Ends: St. Georges / St. Georges
Activities: Village Visits
Activity Level: Variable

Embark on a 12-day cruise through the Southern Caribbean aboard the Star Clipper, starting in St. George’s, Grenada. Experience stunning beaches, vibrant local culture, and historical sites across Tobago, the Grenadines, Martinique, and Barbados.

Cruise Details

Dock going out into the crystal blue ocean

from $2,080

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Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper

Explore Antigua’s vibrant dockyards
Discover Les Saintes’ beaches
Relax on Martinique’s white sands
Stroll Grenada’s aromatic markets

Starts / Ends: St. John's / Bridgetown
Activity Level: Variable

Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.

Cruise Details

from $8,370

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Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant

Relax on Grande Anse Beach
Snorkel Tobago Cays Reefs
Visit Port Elizabeth waterfront
Discover Portsmouth landscapes

Starts / Ends: Anses d'Arlet / Marie Galante
Activities: Scuba Diving
Activity Level: Variable

Explore Guadeloupe and the Southern Caribbean aboard Le Ponant on an 8-day cruise. Swim in Tobago Cays, snorkel at Sandy Island, discover Grande Anse d’Arlet, visit Portsmouth, sail past The Pitons, and experience Creole culture, beaches, reefs, and island towns across multiple Caribbean destinations.

Cruise Details

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