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Top Windward Islands Trips & Tours in February 2023

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Discover Windward Islands in February 2023 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of Bequia, Tobago Cays, Bridgetown, St. Georges, and Dominica during February 2023 as you enjoy snorkeling, small ship cruises, cruises, beaches, and small ship sailing. Prices for trips in February 2023 range from $2,360 to $22,560 for a vacation of 8 to 13 days. Choose any of the below 7 amazing itineraries in February 2023 and customize it to make it your own with the help of one of Adventure Life's expert Windward Islands trip planners.
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White Sand Beach in Barbados
$2,420
EXPLORE

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 in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Join the Royal Clipper on this 8-day cruise through theGrenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts,Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day.From the horseshoe-shaped Carenage at St. …
Cruise Details
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Pelicans hanging out in the ocean
$11,300
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Stand on deck as Sea Cloud’s 30 white sails fill with wind, and measure the passage of time by a distant island’s approach on the horizon.Join thisextraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the …
Cruise Details
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Mountains by the ocean in St Lucia
$3,840
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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 in:
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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Take in the sights, sounds, and colors of Barbados
$4,930
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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Vieux Fort - Bridgetown - 9 Day Itinerary aboard Le Dumont-d'Urville
  • Visit UNESCO World Heritage sites
  • Discover archipelagos of Caribbean
  • Explore landscapes of Indian river
  • See Mayreau's fishes and corals
Starts/ Ends in:
St. Lucia / Bridgetown
Activities:
Hiking, Land & Sea Exploration, Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Call at Dominica's Portsmouth Island, which will enchant you with its pristine mountain sceneries and give you a sight of the island's fascinating flora and animals. Continue north to Les Saintes, a little archipelago off the coast of Guadeloupe that is a favorite anchorage spot with …
Cruise Details
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Pink beach huts in the Caribbean
$2,420
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Windward Islands

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 in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
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Beautiful beach in Dominica
$2,360
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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 in:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this amazing region, there’s a lot of paradise to see. Best of all, …
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Clear water in the bay
$6,400
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The Essential of the Caribbean

13 Day Itinerary aboard Le Dumont-d'Urville
  • Cruise in West Indies
  • Visit heritage sites
  • Discover British Virgin Islands
  • Explore Dominica
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Sail the idyllic waters of theCaribbean Seato discover stunning islands, as well as historical and architectural landmarks. Visit St.Kitts, a volcanic island with sandy beaches and a colonial past. Stop at Anguilla before reaching the British Virgin Islands, which offer gorgeous landscapes. …
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