Windward Islands Beach Trips

from $7,990

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Grenadines & Windwards Yachting

Roundtrip Bridgetown - 8 Day Itinerary aboard Emerald Sakara

• Discover Bequia’s secluded beaches
• Savor Caribbean dining experiences
• Snorkel Tobago Cays' waters
• Admire panoramic views from Mayreau

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Embark on an 8-day cruise aboard the Emerald Sakara, starting and ending in Bridgetown, Barbados. Explore historic towns, relax on stunning beaches, and enjoy snorkeling and water activities in the picturesque Saint Vincent and the Grenadines.

Cruise Details

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from $3,150

SS 25%

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Grenada Roundtrip

Roundtrip St George - 12 Day Itinerary aboard Star Clipper

• Tour St. George's Sendall Tunnel
• Taste Castara Bay Tobago's Creole
• Stroll Admiralty Bay waterfront
• View Saint Pierre colonial ruins

Starts / Ends

St. Georges / St. Georges

Activities

Village Visits, Local Market Visits

Activity Level

Variable

Embark on a 12-day cruise through the Southern Caribbean aboard the Star Clipper, starting in St. George’s, Grenada. Experience stunning beaches, vibrant local culture, and historical sites across Tobago, the Grenadines, Martinique, and Barbados.

Cruise Details

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from $2,030

Air Credit

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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 $2,010

Air Credit

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Grenada to Antigua

St George - St John - 8 Day Itinerary aboard Star Clipper

• Tour St. George's Fort George
• Visit Bequia Port Elizabeth
• Snorkel Tobago Cays
• Relax on Martinique turquoise water

Starts / Ends

St. Georges / St. John's

Activities

Small Ship Sailing, Snorkeling

Activity Level

Variable

Embark on an 8-day cruise from St. George’s, Grenada, aboard the Star Clipper, visiting highlights like Fort George and the Tobago Cays for snorkeling. The journey wraps up in St. Kitts after exploring St. Lucia's Pitons, Martinique's beaches, and Dominica's rainforests.

Cruise Details

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from $3,090

SS 25%

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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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from $2,820

Air Credit

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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.

Cruise Details

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from $2,080

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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.

Cruise Details

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from $2,880

Air Credit

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Aruba to Grenada

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

• Visit Oranjestad to see beaches
• See Willemstad gabled houses
• Tour Curacao inland cunucu
• Swim Charlestown Bay

Starts / Ends

Oranjestad / St. Georges

Activity Level

Variable

Set sail on an 11-day Caribbean cruise aboard the Star Clipper from Aruba to Grenada, exploring vibrant destinations like Oranjestad and Willemstad. Enjoy highlights such as snorkeling in Tobago Cays and visiting St. George’s and its historic sites in Grenada.

Cruise Details

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from $9,440

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Pearls of the Caribbean

Fort-de-France Roundtrip - 8 Day Itinerary aboard Le Bougainville

• Wander at Fort-de-France Harbor
• Discover Union Island Beaches
• Snorkel at Tobago Cays Reefs
• Swim Pompierre Beach Les Saintes

Starts / Ends

Fort de France / Fort de France

Activities

Archaeological Site Visits

Activity Level

Variable

Embark on an 8-day Caribbean cruise from Martinique through the Grenadines aboard Le Bougainville. Explore vibrant towns, secluded beaches, coral reefs, tropical islands, and volcanic landscapes. Snorkel, swim, stroll along scenic shores, and enjoy historic sites.

Cruise Details

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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

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.

Cruise Details

0

from $15,980

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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

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from $6,830

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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

Activities

Scuba Diving

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

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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

Wildlife Viewing, 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.

Cruise Details

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from $22,140

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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.

Cruise Details

0

from $2,820

Air Credit

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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.

Cruise Details

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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.

Cruise Details

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from $2,030

Air Credit

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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.

Cruise Details

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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

0