Caribbean Small Ship Sailing Cruises

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

Embark on an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, visiting beautiful locations like Anguilla, Tortola, and Virgin Gorda. Enjoy duty-free shopping in St. Barts and explore the colonial history of St. Kitts before returning to St. Maarten.

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from $2,010

SS 25%

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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

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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.

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from $2,880

SS 25%

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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 $8,220

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Gliding the Waters of the Windward Islands

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

• Enjoy iconic pitons of Saint Lucia
• Learn about Kalinago culture
• Explore Tobago Cays' coral reefs
• Relax on Marie-Galante's beaches

Starts / Ends

Dominica / Anses d'Arlet

Activities

Scuba Diving

Activity Level

Variable

Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint Vincent and the Grenadines, snorkeling in Tobago Cays' clear waters. Experience sunsets, local culture, and beaches in Marie-Galante. This cruise combines relaxation and adventure in the Caribbean.

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from $3,200

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Eastbound Atlantic Ocean Crossing

Bridgetown - Lisbon - 17 Day Itinerary aboard Royal Clipper

• Explore the east coast of Barbados
• Discover the Azores history
• Visit the Alfama

Starts / Ends

Bridgetown / Lisbon

Activity Level

Variable

Embark on this 17-day Eastbound Atlantic Ocean Crossing cruise aboard Royal Clipper, starting from the port of Bridgetown. Experience the allure of the Azores, and play host to transatlantic yachtsmen, traders, and explorers. It stands on the green and fertile island of Sao Miguel. Finally, conclude your cruise in the city of Lisbon, Portugal.

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from $4,450

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Barbados to Panama

15 Day Itinerary aboard Royal Clipper

• Explore Bridgetown, Barbados
• Enjoy Grenada's unique aromas
• Discover Dutch colonial Curacao
• Transit the historic Panama Canal

Starts / Ends

Bridgetown / Balboa

Activity Level

Variable

Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.

Cruise Details

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from $4,330

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Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper

• Explore Bridgetown’s heritage
• Discover St. George’s coastal views
• Admire Kralendijk’s marine life
• Wander Willemstad’s streets

Starts / Ends

Bridgetown / Balboa

Activities

Wildlife Viewing

Activity Level

Variable

Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.

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from $4,450

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Panama to Antigua

15 Day Itinerary aboard Royal Clipper

• Explore Balboa’s colonial charm
• Transit Panama’s iconic canal
• Discover San Blas culture
• Enjoy Aruba’s clear waters

Starts / Ends

Balboa / St. John's

Activity Level

Variable

Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.

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from $5,610

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Eastbound Atlantic Ocean Crossing

Barbados to France - 29 Day Itinerary aboard Royal Clipper

• See Ponta Delgada, Azores scenery
• See Malaga, Spain's architecture
• Visit Mallorca’s Gothic cathedral
• Visit Calvi’s coastal citadel

Starts / Ends

Bridgetown / Nice

Activity Level

Variable

Set sail on a 29-day Eastbound Atlantic Ocean cruise aboard Royal Clipper. Enjoy sailing, historic ports, and scenic coastal landscapes.

Cruise Details

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from $3,150

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Panama to Aruba

12 Day Itinerary aboard Star Clipper

• Transit the Panama Canal locks
• Walk colonial Balboa streets
• Explore forts in Portobelo
• Visit San Blas and Guna villages
• See Cartagena and Santa Marta

Starts / Ends

Balboa / Oranjestad

Activities

Local Market Visits

Activity Level

Variable

Sail the Panama Canal on a 10-day Star Clippers cruise through Central America. Begin in Balboa, then transit the Panama Canal and see the locks in action. Explore Spanish forts in Portobelo, meet the Guna people in the San Blas Islands, and discover Colombia’s coastal cities of Cartagena and Santa Marta. Enjoy scenic days under sail.

Cruise Details

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from $2,940

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Westbound Atlantic Ocean Crossing

Lisbon - Barbados - 16 Day Itinerary aboard Royal Clipper

• Explore Lisbon’s vibrant streets
• Discover Portimão’s historic charm
• Wander Funchal’s lush landscapes
• Cruise Barbados’ stunning shores

Starts / Ends

Lisbon / Bridgetown

Activity Level

Variable

Sail across the Atlantic on this 16-day cruise aboard the Royal Clipper, blending culture and adventure. Discover Lisbon’s charm, Portimao’s historical treasures, Madeira’s vibrant nightlife, and Barbados’ stunning shores, with serene days at sea in between.

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from $2,970

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Westbound Atlantic Ocean Crossing

Las Palmas to Barbados - 16 Day Itinerary aboard Star Flyer

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage all the way to the stunningly beautiful Caribbean Islands.

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from $2,820

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Westbound Atlantic Ocean Crossing

16 Day Itinerary aboard Star Clipper

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Starts / Ends

Las Palmas / Bridgetown

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage to the stunningly beautiful Caribbean Islands.

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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.

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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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from $4,130

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Westbound Atlantic Ocean Crossing

Malaga - Bridgetown - 23 Day Itinerary aboard Star Clipper

• Visit Safi port
• View Arrecife golden sand beach
• See Bridgetown Trafalgar Square
• View Las Palmas volcanic crater

Starts / Ends

Malaga / Bridgetown

Activities

Archaeological Site Visits

Activity Level

Variable

Set sail on a 23-day transatlantic cruise from Malaga to Barbados on the Star Clipper, exploring stunning sites like the Alhambra in Spain, the Hassan II Mosque in Morocco, and the volcanic landscapes of the Canary Islands. Conclude your journey in Bridgetown, Barbados, visiting historic landmarks.

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