Set Sail on Small Ship Cruises in Antigua for Memorable Adventures

Learn about Spanish colonial history in Old San Juan

Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Kaia

Visit Culebra Flamenco Beach
Tour St. John Mongoose Junction
Discover Cruz Bay bustling bay
Walk Philipsburg street markets

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

Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring Vieques, Cruz Bay, and Jost Van Dyke's stunning beaches. Visit Gustavia in Saint Barthelemy, experiencing its unique French culture before concluding the journey in St. John's, Antigua.

Cruise Details

from $6,745

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Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Kaia

Discover Basseterre architecture
See Iles des Saintes Fort Napoleon
Walk Gustavia painted wooden houses
Tour Virgin Gorda granite boulders

Starts / Ends: St. John's / San Juan
Activities: Village Visits, Local Market Visits
Activity Level: Variable

Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from Antigua, visiting St. Kitts, Guadeloupe, and Saint-Barthelemy, before exploring the British Virgin Islands' iconic sites. End your journey in San Juan, Puerto Rico, the oldest European settlement in the Americas.

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, Rainforest Exploration, Kayaking
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

Learn about the history of the Caribbean

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

Panoramic view from Shirley Heights, Antigua, showing English Harbor and Caribbean landscape

from $6,995

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Pirate Islands With A Yachtie Vibe

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit

Explore Gustavia harbor
Visit Shirley Heights, Antigua
Explore The Baths, Virgin Gorda
Sail Sir Francis Drake Channel
Experience Virgin Islands fun

Starts / Ends: Philipsburg / Philipsburg
Activity Level: Variable

Sail 8 days aboard Sea Cloud Spirit on a Caribbean round-trip from Philipsburg, St. Maarten. Explore Gustavia, St. John’s, Virgin Gorda, Jost van Dyke, and Norman Island with beaches, sailing, and historic sights.

Cruise Details

from $2,620

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Windward Islands

Roundtrip Bridgetown - 8 Day Itinerary aboard Royal Clipper

Stroll through historic Bridgetown
Enjoy sunny Rodney Bay
Swim in South Friar's Bay
Tour historic St. Kitts

Starts / Ends: Bridgetown / Bridgetown
Activities: Small Ship Sailing, Snorkeling, Archaeological Site Visits, Hiking
Activity Level: Variable

Set sail on an 8-day Caribbean cruise aboard the Royal Clipper, visiting Saint Lucia, Dominica, and Antigua, among other beautiful islands. Enjoy activities like hiking, snorkeling, and water sports before concluding your journey in Bridgetown.

Cruise Details

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.

Cruise Details

Beach, harbor and village of Terre-de-Haut

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
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.

Cruise Details

Relax on the pristine beaches of the Virgin Islands

from $8,095

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Tropical Charms of the Caribbean

Roundtrip Sint Maarten - 10 Day Itinerary aboard Emerald Sakara

Tour St. John's Nelson's Dockyard
Tour Iles des Saintes Fort Napoleon
Visit Friars Bay Brimstone Hill
Wander Virgin Gorda The Baths rocks

Starts / Ends: Philipsburg / Philipsburg
Activity Level: Variable

Experience a 10-day cruise from Philipsburg, Sint Maarten, aboard the Emerald Sakara, visiting stunning beaches and local markets in Guadeloupe and exploring the British Virgin Islands. Enjoy unique landscapes in Montserrat and relax on Virgin Gorda's beautiful shores before returning to Philipsburg.

Cruise Details

Stroll along the beautiful beaches of the Caribbean

from $3,860

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Grenadine Islands Christmas Cruise

Roundtrip Bridgetown - 11 Day Itinerary aboard Royal Clipper

Relax on beaches in Martinique
Snorkel reefs in Terre de Haut
Swim in South Friar's Bay
Explore the Tobago Cays

Starts / Ends: Bridgetown / Bridgetown
Activity Level: Variable

Set sail on an 11-day New Year's Caribbean cruise aboard the Royal Clipper, visiting beautiful spots like Grenada, St. Lucia, and Dominica. Enjoy snorkeling in Tobago Cays, relaxing at Diamond Falls, and exploring historic sites in Antigua and St. Kitts before concluding your adventure in Bridgetown.

Cruise Details

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.

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

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