Small Ship Cruises to Lesser Antilles

from $9,990

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Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra

• Explore Anguilla’s coral coastlines
• Visit Virgin Gorda granite boulders
• Discover Norman Island's coves
• Relax on Anegada’s remote sands

Starts / Ends

Marigot / Marigot

Activity Level

Variable

Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.

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from $9,990

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra

• Explore Prickly Pear Cays waters
• Admire Nevis’ Georgian buildings
• Visit Soufriere’s volcanic springs
• Wander Bridgetown’s streets

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.

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from $9,990

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Quintessential Caribbean

St Thomas - San Juan - 8 Day Itinerary aboard Emerald Sakara

• Explore Cruz Bay town
• Visit Nevis plantations
• Discover Nelson’s Dockyard
• Swim Prickly Pear Cays

Starts / Ends

St. Thomas / San Juan

Activity Level

Variable

Explore the Caribbean on an 8-day cruise from Saint Thomas to San Juan aboard Emerald Sakara. Visit Saint John, Nevis, Guadeloupe, Antigua, Saint Barthélemy, and the British Virgin Islands. Discover UNESCO-listed landmarks, swim in clear waters, and experience regional architecture, food, and history throughout the journey.

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from $7,990

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara

• Discover Anguilla’s coral coast
• Explore Gustavia’s boutiques
• Wander Nevis seaside buildings
• Visit Antigua’s English Harbor

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbor’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise

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from $8,390

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Caribbean Yachting Discovery

St John - St Thomas - 8 Day Itinerary aboard Emerald Azzurra

• Visit Barbuda's pink-sand beaches
• Explore Norman Island hidden caves
• Sail luxury yacht through Caribbean
• Relax on Virgin Gorda beaches

Starts / Ends

St. John's / St. Thomas

Activity Level

Variable

Embark on an 8-day Caribbean cruise aboard Emerald Azzurra from Antigua to St. Thomas. Explore vibrant ports like Barbuda, Illes des Saintes, and Virgin Gorda. Discover unique sites such as Norman Island’s caves and the markets of Guadeloupe. Travel aboard a luxury yacht, exploring beaches, history, and local culture at each stop.

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from $11,990

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Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra

• Visit UNESCO-listed Nelson's dock
• Discover Iles des Saintes town
• Stroll Gustavia’s colorful street
• Dip into a therapeutic mud bath

Starts / Ends

Bridgetown / Marigot

Activity Level

Variable

Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.

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from $2,820

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Antigua to Grenada

Antigua to Grenada - 11 Day Itinerary aboard Star Clipper

• Explore Gustavia boutiques
• Swim Norman Island coves
• Visit Jost van Dyke beaches
• Relax in St. Kitts landscapes

Starts / Ends

St. John's / St. Georges

Activities

Snorkeling, Hiking

Activity Level

Variable

Set sail on an 11-day Caribbean cruise aboard Star Clipper. Depart from Antigua and explore St. Barts, the British Virgin Islands, St. Kitts, Martinique, Bequia, and Grenada. Discover historic harbors, swim in crystal waters, and relax on world-class beaches.

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from $21,180

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Discover the Yachting Islands of the Caribbean

Roundtrip Saint John’s - 15 Day Itinerary aboard Emerald Azzurra

• Explore Barbuda’s iconic pink sands
• Visit Les Saintes’ quaint towns
• Discover Deshaies’ lush hills
• Swim off Norman Island’s shores

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Embark on a 15-day cruise with Emerald Azzurra, exploring the Caribbean from St. John’s, Antigua, with stops at stunning destinations like Barbuda, Guadeloupe, and the British Virgin Islands. Enjoy snorkeling in Culebra and the relaxed vibe of Esperanza on Vieques, all amidst beautiful beaches and vibrant island culture.

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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 $15,980

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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

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 $4,800

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San Juan to Bridgetown

San Juan - Bridgetown - 8 Day Itinerary aboard Silver Spirit

• Explore Historic San Juan
• Snorkel Trunk Bay Reefs
• Stroll Willemstad Waterfront
• Explore Bridgetown

Starts / Ends

San Juan / Bridgetown

Activities

Wildlife Viewing, Local Market Visits, Archaeological Site Visits, Spa Relaxation, Whale Watching

Activity Level

Variable

Set sail on an 8-day Silver Spirit voyage from San Juan to Bridgetown. Discover Caribbean charm in St. John’s national park, Nevis’s golden beaches, Bonaire’s vibrant reefs, and Curaçao’s colorful Dutch heritage. Enjoy time at sea before disembarking in Bridgetown, where rich culture meets island beauty.

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from $7,990

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Quintessential Caribbean

San Juan - St Thomas - 8 Day Itinerary aboard Emerald Sakara

• Relax on Prickly Pear Cays' beaches
• Visit Guadeloupe’s fishing village
• Visit port of Falmouth Harbor
• Wander through lively Cruz Bay

Starts / Ends

San Juan / St. Thomas

Activity Level

Variable

Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays.

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from $21,980

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Discover the Yachting Islands of the Caribbean

Roundtrip San Juan - 15 Day Itinerary aboard Emerald Azzurra

• Snorkel Culebra’s coral reefs
• Wander Vieques’ Esperanza
• Explore St. John’s plantation ruins
• Stroll Philipsburg’s streets

Starts / Ends

San Juan / San Juan

Activities

Village Visits, Kayaking

Activity Level

Variable

Embark on a 15-day Caribbean cruise from San Juan aboard Emerald Azzurra, exploring serene spots like Culebra, Vieques, and St. Barts. Experience stunning beaches, rich culture, and scenic ports, all in a relaxed yacht-style setting.

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from $9,190

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Splendours of the Caribbean

San Juan - St. Thomas - 7 Day Itinerary aboard Emerald Sakara

• Tour Nelson’s Dockyard
• Explore Nevis Island plantations
• Walk through Gustavia
• Swim Prickly Pear Cays

Starts / Ends

San Juan / St. Thomas

Activities

Urban Exploration

Activity Level

Variable

Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.

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from $2,820

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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

Activities

Small Ship Sailing

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 $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

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 $8,390

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Caribbean Yachting Hideaways

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

• Discover Culebra Island’s shores
• Explore Vieques Island waterfront
• Tour St. John’s Annaberg ruins
• Relax on Jost Van Dyke’s White Bay

Starts / Ends

San Juan / St. John's

Activity Level

Variable

Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.

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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.

Cruise Details

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