Leeward Islands Small Ship Cruises

from $9,190

2for1

EXPLORE

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

Village Visits, 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.

Cruise Details

0

from $2,820

EXPLORE

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.

Cruise Details

0

from $9,990

2for1

EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra

• Soak in Soufriere’s volcanic spring
• Explore Les Saintes’ French charm
• Visit Antigua’s Nelson’s Dockyard
• Stroll Nevis’ Georgian towns

Starts / Ends

Bridgetown / Marigot

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.

Cruise Details

0

from $8,390

2for1

EXPLORE

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.

Cruise Details

0

from $11,990

2for1

EXPLORE

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.

Cruise Details

0

from $5,850

Save 10%

EXPLORE

Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Bellot

• See UNESCO World Heritage Sites
• Visit the Grenadine Islands
• Observe marine animals
• Enjoy the beach on Mayreau Island

Starts / Ends

Fort de France / Fort de France

Activity Level

Variable

Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!

Cruise Details

0

from $2,030

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

0

from $3,420

EXPLORE

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

Activities

Small Ship Sailing

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.

Cruise Details

0

from $21,340

2for1

EXPLORE

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.

Cruise Details

0

from $15,980

2for1

EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra

• Explore Anguilla, serene landscapes
• Savor Barbados’s cultural delights
• Visit Antigua’s historic dockyard
• Stroll Nevis’s serene beaches

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.

Cruise Details

0

from $19,990

2for1

EXPLORE

Island Odyssey: Bahamas to the Grenadine

Nassau - Bridgetown - 11 Day Itinerary aboard Scenic Eclipse

• Explore Nassau’s vibrant capital
• Visit Staniel Cay’s beaches
• Discover San Salvador’s coral reefs
• Stroll St. Barts iconic Shell Beach

Starts / Ends

Nassau / Bridgetown

Activities

Kayaking, Stand Up Paddle Boarding, Helicopter Tours

Activity Level

Variable

Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.

Cruise Details

0

from $3,090

EXPLORE

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.

Cruise Details

0

from $15,980

2for1

EXPLORE

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.

Cruise Details

0

from $4,800

EXPLORE

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.

Cruise Details

0

from $2,080

EXPLORE

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

0

from $2,820

EXPLORE

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.

Cruise Details

0

from $8,220

EXPLORE

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.

Cruise Details

0

from $6,800

Save 10%

EXPLORE

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.

Cruise Details

0