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Top Windward Islands Trips & Tours in January 2025

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Discover Windward Islands in January 2025 on one of these 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of Bequia, Dominica, Soufriere, Iles des Saintes, and Gustavia during January 2025 as you enjoy snorkeling, cruises, small ship sailing, small ship cruises, and active. Prices for trips in January 2025 range from $1,640 to $23,190 for a vacation of 8 to 10 days. Choose any of the below 6 itineraries in January 2025 and customize it when you contact one of Adventure Life's expert Windward Islands trip planners.
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White Sand Beach in Barbados
$1,700
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:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Variable
Join the Royal Clipper on this 8-day cruise through the Grenadine 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
0
Pelicans hanging out in the ocean
$9,658
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:
Variable
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 this extraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers …
Cruise Details
0
Relax on the beaches of St. Maarten
$8,995
EXPLORE

Barefoot through Balmy January

St Maarten to Barbados - 10 Day Itinerary aboard Sea Cloud
  • Explore St. Maarten’s charm
  • Relax on Bequia beaches
  • Snorkel in Tobago Cays
  • Discover Soufriere’s sulfur springs
Starts / Ends:
Philipsburg / Barbados
Activities:
Small Ship Sailing, Snorkeling
Activity Level:
Variable
Embark on a 10-day journey through the Caribbean, starting in Philipsburg, St. Maarten. Discover European charm in the heart of the Caribbean, stroll along the Boardwalk, or relax on Great Bay Beach. Visit the island of St. Barths, renowned for its elegant atmosphere and vibrant harbor. In …
Cruise Details
0
Beautiful beach in Dominica
$8,200
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, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Experience an 8-day Caribbean cruise aboard Le Ponant. Explore the wild landscapes of Dominica and navigate the mangroves of the Indian River on a local boat, surrounded by green herons and pelicans. Meet the Kalinago people, who share their history and local cuisine, offering insight into their …
Cruise Details
0
Pink beach huts in the Caribbean
$1,700
EXPLORE

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:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
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 …
Cruise Details
0
Relax on the beaches of St. Maarten
$1,640
EXPLORE

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
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Embark on an 8-day cruise aboard the Star Flyer. 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 unique region, …
Cruise Details
0
1-6 of 6 Results
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