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All Windward Islands Luxury Small Ship Cruises

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Explore Windward Islands in style and comfort on one of Adventure Life's luxury Windward Islands tours. Enjoy small ship cruises, luxury, cruises, snorkeling, and beaches and explore our favorite luxury destinations including Bridgetown, St. Georges, Tobago Cays, Mayreau, and Bequia. Experience fine local cuisine prepared by local chefs and explore the surroundings with the top local English-speaking guides available. Thousands of travelers have trusted Adventure Life to plan a flawless luxury-class Windward Islands trip. Just tell us about your ideal Windward Islands trip, and we'll help you make it a reality.
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Stroll along the white sandy beaches of St. Barth's
$10,185
EXPLORE

Relaxed Festive Days Under Palms

Round-trip Philipsburg - 17 Day Itinerary aboard Sea Cloud
  • See St Barths' luxurious lifestyle
  • Visit beautiful islands
  • Discover volcanoes
  • Observe incredible sunsets
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Fall in love with the region's sun, sand, and culture. Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg …
Cruise Details
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Mountains by the ocean in St Lucia
$3,840
EXPLORE

Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Dumont-d'Urville
  • 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, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Dumont-d'Urville on this 9-day cruise combining long, white-sand beaches and the laid-back Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its …
Cruise Details
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The sun sets off the Canary Islands
$14,245
EXPLORE

Dream of A Lifetime: Transatlantic Crossing

18 Day Itinerary aboard Sea Cloud
  • Follow Columbus's course
  • Sail across the Atlantic Ocean
  • Enjoy an offshore sailing adventure
  • Observe incredible sunsets
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Follow the route Columbus took across the Atlantic as you set sail for new horizons on a voyage of discovery. Discover this 17-day pure sailing adventure where for two whole weeks, the expansive ocean is the home of Sea Cloud. Water currents and trade winds are all that propel the yacht forwards. …
Cruise Details
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Relax on the beaches of the Caribbean
$6,180
EXPLORE

Christmas and New Year in the Caribbean

Fort-de-France - Santo Domingo - 13 Day Itinerary aboard Le Dumont-d'Urville
  • Explore gardens and parks
  • See UNESCO World Heritage Sites
  • Swim in crystal clear waters
  • Learn the history of the region
Starts / Ends:
Fort de France / Santo Domingo
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Board the luxurious Le Dumont-d'Urville to celebrate Christmas and ring in the New Year with this 13-day cruise. Set sail from Fort-de-France and cruise to some of the finest islands in the Caribbean. From the lush rainforest and mountainous terrain of Dominica, to the warm, clear waters of …
Cruise Details
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Take a leisurely stroll through beautiful Bridgetown
$4,900
EXPLORE

San Juan to Bridgetown

10 Day Itinerary aboard Silver Dawn
  • Head up to Gustavia Lighthouse
  • Visit St. Barts
  • Sail through Fort-de-France
  • Marvel around Bequia
Starts / Ends:
San Juan / Bridgetown
Activities:
Biking, Hiking, Kayaking, Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
This 10-day Caribbean cruise is designed to showcase the Caribbean's vibrant sightseeing, delicious cuisine, and vibrant nightlife. Explore the sapphire waters of San Juan, a beach-blessed star of these turquoise waters, with huge fortresses, airy plazas, and absolute Caribbean splendour. No …
Cruise Details
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Enjoy the beautiful blue Caribbean
$3,840
EXPLORE

In the heart of the West Indies : Bridgetown - Vieux Fort

9 Day Itinerary aboard Le Dumont-d'Urville
  • Visit Barbados and St. Lucia
  • Tour Saint Vincent & the Grenadine
  • Discover long white-sand beaches
  • Enjoy the beach on Mayreau Island
Starts / Ends:
Les Saintes / Bridgetown
Activities:
Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
This 9-day trip on Le Dumont-d'Urville combines extensive white-sand beaches with comfortable Creole living. After boarding in Bridgetown, Barbados, your cruise anchors in the Tobago Cays National Park. Amazing underwater species can be found in this rosary of islands connected by the West …
Cruise Details
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