Best Small Ship Caribbean Cruises

from $2,020

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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.

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from $2,020

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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 $1,960

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Leeward Islands

8 Day Itinerary aboard Star Flyer

• Visit Dominica Island
• Snorkel at Iles des Saintes
• Sail across Rivière Salée
• Enjoy Gustavia's unique charm

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.

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from $1,960

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Treasure Islands

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 $1,970

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Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Sail Sir Francis Drake Channel
• Stroll Norman Island's beach
• Tour Basseterre's old plantations

Starts / Ends

St. John's / St. John's

Activities

Snorkeling, Village Visits

Activity Level

Variable

Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.

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from $21,340

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

• Explore Anguilla’s turquoise waters
• Stroll through Gustavia
• Admire Nevis’ tranquil shores
• Visit Antigua’s Falmouth Bay

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

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from $15,180

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

• Explore Bridgetown’s capital
• Wander Speightstown’s streets
• Discover Kingstown’s gardens
• Unwind on Bequia Island

Starts / Ends

Bridgetown / Marigot

Activities

Kayaking

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

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from $3,090

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Jamaica to Antigua

12 Day Itinerary aboard Star Clipper

• Swim in Montego Bay's waters
• Explore Santo Domingo
• Visit the Treasure Island
• Hike Virgin Gorda trails

Starts / Ends

Port Antonio / St. John's

Activity Level

Variable

Explore a paradise of vibrant coral reefs, powder-soft sand, and warm island hospitality on this 12-day cruise from Jamaica to Antigua aboard Star Clipper. Experience crystal-clear water, bright skies, and gentle breezes. Relish in the beauty of untouched beaches and become enchanted by seductive scents and rhythms.

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from $8,050

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Grenada to Antigua

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

• Explore St. George’s harbor
• Experience Charlotteville coast
• Relax at Englishman’s Bay
• Wander through Admiralty Bay

Starts / Ends

St. Georges / St. John's

Activity Level

Variable

Take an 11-day cruise on the Star Clipper from St. George's, Grenada to St. John's, Antigua, exploring secluded bays and historic towns in Tobago and the Grenadines. Enjoy highlights like snorkeling in Tobago Cays and relaxing on beautiful beaches, while immersing yourself in vibrant local cultures.

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from $7,590

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Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara

• Explore the pristine beaches
• Snorkel in crystal-clear waters
• Relax on secluded Gordon’s Beach
• Explore Grand Turk’s beaches

Starts / Ends

San Juan / Miami

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites.

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from $11,600

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Bridgetown to Bridgetown

22 Day Itinerary aboard Silver Spirit

• Explore top Caribbean islands
• Visit Bequia and Iles des Saintes
• Explore Gustavia’s historic harbor
• Experience the Caribbean culture

Starts / Ends

Bridgetown / Bridgetown

Activities

Small Ship Sailing, Wildlife Viewing, Local Market Visits, Spa Relaxation, Archaeological Site Visits

Activity Level

Variable

Sail round-trip from Bridgetown aboard Silver Spirit on a 22-day Caribbean cruise. Explore top islands like St. Lucia, Martinique, and Barbados, plus hidden gems like Bequia and Iles des Saintes. Enjoy beach days, island tours, and cultural stops with long port calls.

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from $3,090

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Grenada to Grenada

Roundtrip St George - 12 Day Itinerary aboard Star Clipper

• Explore St. George’s Fort George
• Discover Charlotteville’s Tobago
• Unwind on Carriacou beach
• Visit Martinique ruins

Starts / Ends

St. Georges / St. Georges

Activity Level

Variable

Set sail on a 12-day cruise aboard the Star Clipper, exploring stunning islands like Tobago and Martinique, with highlights including the Tobago Cays and St. Lucia's waterfalls. Experience the Caribbean's serene beauty and rich culture while enjoying activities like snorkeling and history.

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from $8,050

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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 $6,800

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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 9 Day Itinerary aboard Le Bellot

• Visit UNESCO World Heritage sites
• Visit Portsmouth, Dominica
• Explore Les Saintes, Guadeloupe
• See Mayreau's fishes and corals

Starts / Ends

Les Saintes / Bridgetown

Activities

Hiking

Activity Level

Variable

From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the Caribbean Sea. Before disembarking in Vieux Fort, explore long stretches of white-sand beaches, idyllic turquoise waters, and the laid-back island way of life.

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from $8,370

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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 $3,420

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Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - 21 Day Itinerary aboard Star Flyer

• Explore Philipsburg’s Dutch side
• Experience Marigot’s markets
• Unwind while crossing the Atlantic
• Visit Ponta Delgada’s churches

Starts / Ends

Philipsburg / Malaga

Activity Level

Variable

Set sail on a 21-day cruise aboard the Star Flyer, starting in Philipsburg and visiting Ponta Delgada in the Azores. End your journey in Malaga, Spain, exploring its Moorish heritage while enjoying 18 days at sea.

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from $4,350

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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.

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