Top Caribbean Trips & Tours

from $2,010

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Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Explore Nevis sugar plantations
• Visit Dominica boiling lakes
• Snorkel Terre-de-Haut blue waters
• Swim South Friars Bay clear waters

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Philipsburg / Philipsburg

Activity Level

Variable

Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.

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from $2,010

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Treasure Islands

St. Maarten Roundtrip - 8 Day Itinerary aboard Star Flyer

• Visit Virgin Gorda's famous “Baths”
• Enjoy the lifestyle of Soper's Hole
• Walk the streets of Basseterre
• Relax on famous St. Barts

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!

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from $2,080

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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.

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from $2,080

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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.

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from $2,010

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Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Explore Nevis sugar plantations
• Tour Dominica rainforests
• Snorkel Terre-de-Haut waters
• Visit famous Nelson's Dockyard

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Embark on an 8-day roundtrip cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring St. Maarten, Nevis, Dominica, Antigua, and St. Barts. Experience stunning beaches, vibrant culture, and unique natural landscapes across the Leeward Islands.

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from $2,880

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Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper

• Explore St. George’s panoramic view
• Discover Charlotteville coastline
• Unwind at Englishman’s Bay
• Visit Martinique ruins

Starts / Ends

St. Georges / St. Georges

Activity Level

Variable

Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.

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from $2,880

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Aruba to Grenada

Oranjestad - St. George - 11 Day Itinerary aboard Star Clipper

• Visit Oranjestad to see beaches
• See Willemstad gabled houses
• Tour Curacao inland cunucu
• Swim Charlestown Bay

Starts / Ends

Oranjestad / St. Georges

Activity Level

Variable

Set sail on an 11-day Caribbean cruise aboard the Star Clipper from Aruba to Grenada, exploring vibrant destinations like Oranjestad and Willemstad. Enjoy highlights such as snorkeling in Tobago Cays and visiting St. George’s and its historic sites in Grenada.

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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

Local Market 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.

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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.

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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.

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from $2,010

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Sail Sir Francis Drake Channel
• Swim Virgin Gorda Baths
• Hike Jost van Dyke trails

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Set sail on an 8-day round-trip cruise from St. John’s, Antigua, aboard the Star Clipper, exploring St. Barts, the British Virgin Islands, and Anguilla. Highlights include duty-free shopping, scenic hikes, and beautiful beaches before concluding in Antigua.

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from $2,010

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

• Hike St. Kitts rainforests
• Tour Basseterre colonial history
• Shop Philipsburg Dutch bargains
• Explore Tortola to see Soper's Hole

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Experience an 8-day round-trip cruise from St. John's, Antigua, aboard the Star Clipper, visiting destinations like St. Barts, the British Virgin Islands, and St. Maarten. Enjoy duty-free shopping, stunning beaches, and historic sites before concluding your journey in Antigua.

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from $2,010

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Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Visit Anguilla's white sand coves
• Tour Tortola to see Soper's Hole
• Swim South Friars Bay waters
• Hike Jost Van Dyke trails

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts.

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from $2,010

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Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Swim Gustavia beaches
• Visit Nelson's Dockyard ruins
• Snorkel Terre-de-Haut waters
• Hike Dominica trails

Starts / Ends

Philipsburg / Philipsburg

Activities

Snorkeling

Activity Level

Variable

Embark on an 8-day Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring charming towns, lush rainforests, and beautiful beaches. Enjoy duty-free shopping in Gustavia before returning to St. Maarten.

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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

Activities

Rainforest Exploration

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.

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from $13,695

EBD 30%

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Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Philipsburg - 17 Day Itinerary aboard Sea Cloud Spirit

• Experience Transatlantic Crossing
• See the Gran Canaria landscapes
• Explore Las Palmas old town
• Climb rigging and set sails

Starts / Ends

Las Palmas / Philipsburg

Activity Level

Variable

Experience 17 days aboard Sea Cloud Spirit on a transatlantic crossing from Las Palmas to Philipsburg. Relax on deck, enjoy wellness programs, and explore Gran Canaria’s landscapes before arriving in the Caribbean.

Cruise Details

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from $13,655

EBD 30%

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Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Bridgetown - 18 Day Itinerary aboard Sea Cloud II

• Experience Transatlantic Crossing
• Sail under full sails
• Visit Santa Ana Cathedral
• Explore Bridgetown, Barbados

Starts / Ends

Las Palmas / Bridgetown

Activities

Small Ship Sailing, Village Visits

Activity Level

Variable

Take part in an 18-day transatlantic cruise aboard Sea Cloud II from Las Palmas, Gran Canaria to Bridgetown, Barbados. Relax under full sails, explore Gran Canaria’s landscapes, and discover Bridgetown’s UNESCO World Heritage colonial architecture and beaches.

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