Sailboat Cruises in Lesser Antilles

from $2,080

SS 25%

EXPLORE

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

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from $2,880

SS 25%

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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.

Cruise Details

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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

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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

Activities

Wildlife Viewing

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

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from $2,010

SS 25%

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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

Starts / Ends

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.

Cruise Details

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from $2,010

SS 25%

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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!

Cruise Details

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from $6,995

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Across A Sea Of Idyllic Islands

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit

• Explore St. Maarten’s cultures
• Visit Virgin Gorda’s Baths
• Discover Jost van Dyke
• Wander Gustavia, St. Barths

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Sail 8 days aboard Sea Cloud Spirit through the Caribbean’s Lesser Antilles & Grenadines. Discover St. Maarten, Virgin Gorda, Jost van Dyke, Norman Island, St John’s, and St. Barths while enjoying authentic tall-ship sailing and idyllic island scenery.

Cruise Details

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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.

Cruise Details

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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

Snorkeling, Small Ship Sailing, 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.

Cruise Details

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from $3,150

SS 25%

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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, 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.

Cruise Details

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from $2,210

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Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Visit Gustavia French boutiques
• Hike Jost Van Dyke scenic trails
• Tour Tortola to see Soper's Hole
• Explore Basseterre landmarks

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.

Cruise Details

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from $2,010

SS 25%

EXPLORE

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.

Cruise Details

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from $2,010

SS 25%

EXPLORE

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

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from $2,010

SS 25%

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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.

Cruise Details

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from $2,010

SS 25%

EXPLORE

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.

Cruise Details

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from $2,010

SS 25%

EXPLORE

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.

Cruise Details

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from $2,010

EXPLORE

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

Embark on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Visit Anguilla's beaches, explore the British Virgin Islands, hike Jost Van Dyke, and enjoy shopping in St. Barts while uncovering historical sites and natural beauty.

Cruise Details

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from $2,010

SS 25%

EXPLORE

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.

Cruise Details

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