Discover 8-Day Leeward Islands Cruises

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 $7,990

2for1

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Caribbean Yachting Discovery

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

• Explore Barbuda's pink beaches
• Discover Deshaies’ architecture
• Visit Gustavia’s charming boutiques
• Experience Virgin Gorda’s baths

Starts / Ends

St. John's / San Juan

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht 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 $7,740

2for1

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Caribbean Yachting Hideaways

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

• Visit The Baths’ granite formation
• Explore Culebra's white-sand beach
• Experience swimming off the yacht
• Discover the history of St. John

Starts / Ends

St. Thomas / Antigua

Activities

Hiking, Kayaking, Adventure Options

Activity Level

Variable

Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz Bay’s scenic hikes, and Virgin Gorda’s famous Baths. Discover Philipsburg’s vibrant culture, Gustavia’s idyllic beaches, and Montserrat’s volcanic history.

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from $7,590

2for1

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Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara

• Explore Saint John's pristine beach
• Stroll Philipsburg's lively markets
• Snorkel Norman Island's caves
• Visit 'The Baths' in Virgin Gorda

Starts / Ends

St. Thomas / St. Thomas

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty. Philipsburg’s lively port, Gustavia’s charming streets, and tranquil Saint John Island round out this cruise.

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from $7,590

2for1

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Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Azzurra

• Dive in Anguilla
• Explore Virgin Gorda
• Discover Anegada
• Experience Jost van Dyke

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 $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 $5,245

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A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit

• Explore Old San Juan's forts
• Enjoy salsa music
• Sail in the British Virgin Islands
• Explore unique rock formations

Starts / Ends

San Juan / San Juan

Activity Level

Variable

Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and salsa-filled cafes. Discover UNESCO-listed sites like La Fortaleza and Fort San Felipe del Morro, resonating with centuries of history and cultural vibrancy.

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from $7,990

2for1

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara

• Experience Falmouth's historic port
• Discover Soufriere's Sulphur Spring
• Visit Falmouth Harbour in Antigua
• Explore Nelson’s Dockyard

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 Harbour’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 $7,990

2for1

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Quintessential Caribbean

8 Day Itinerary aboard Emerald Sakara

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

Starts / Ends

San Juan / St. Thomas

Activities

Urban Exploration, Archaeological Site Visits, Local Market Visits

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 Harbour, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays. Enjoy unique experiences and stunning landscapes throughout your cruise.

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from $7,590

2for1

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra

• Explore Bridgetown's culture
• Stroll Gustavia's colorful streets
• Admire Marigot’s scenic coastline
• Savor Soufriere's delicious cuisine

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.

Cruise Details

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from $7,590

2for1

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra

• Explore Bridgetown's culture
• Stroll Gustavia's colorful streets
• Admire Marigot’s scenic coastline
• Savor Soufriere's delicious cuisine

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

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from $7,990

2for1

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara

• Explore Bridgetown's culture
• Stroll Gustavia's colorful streets
• Admire Marigot’s scenic coastline
• Savor Soufriere's delicious cuisine

Starts / Ends

Bridgetown / Marigot

Activities

Wildlife Viewing, Small Ship Sailing, Village Visits

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Sakara, 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

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from $2,020

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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.

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from $2,480

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Western Antilles

Saint Martin to Barbados - 8 Day Itinerary aboard SH Vega

• Explore Philipsburg, Sint Maarten
• Discover the town of Gustavia
• Explore the village of Deshaies
• Admire the Pitons in Soufriere
• Discover Saint-Pierre, Martinique
• Explore Bridgetown, Barbados

Starts / Ends

Philipsburg / Bridgetown

Activity Level

Variable

Explore the Caribbean in this 8-day itinerary. Start in Philipsburg, Sint Maarten, Gustavia, Saint-Barthelemy, Deshaies in Guadeloupe, Saint-Pierre, Martinique, Soufriere, St Lucia, and conclude in Bridgetown, Barbados.

Cruise Details

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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.

Cruise Details

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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, Snorkeling

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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