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Leeward Islands Tours in 2026

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Explore the stunning Leeward Islands in the Caribbean on our 9 captivating tours for 2026. Nestled in this tropical paradise, our tours offer a perfect blend of white sandy beaches, crystal-clear waters, and vibrant local cultures, providing an unforgettable experience in the heart of the Lesser Antilles. Over a range of 8 to 12 days, you will have the opportunity to discover the unique charm of each island in the Leeward chain, from the lush landscapes of Antigua to the volcanic peaks of Montserrat. With activities such as snorkeling, hiking, and local market visits, there's something for every type of traveler. Starting at $1,640 to $30,890, these tours promise a journey filled with relaxation, adventure, and cultural immersion. To embark on a Caribbean adventure that will create lasting memories, contact one of Adventure Life's Caribbean specialists for help planning your next seamless trip in 2026.
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    • Leeward Islands
Tropical waterfall and turquoise pool in lush forest
$1,640
EXPLORE

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
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
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
Visit beautiful Norman Island
$7,590
EXPLORE

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
Activities:
Archaeological Site Visits, Local Market Visits, Snorkeling
Activity Level:
Variable
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Saint Thomas. Discover Virgin Gorda, home to The Baths, a mesmerizing collection of natural pools and grottoes formed by massive granite boulders. Sail to Norman Island, renowned for its crystal-clear waters and vibrant …
Cruise Details
0
Gustavia Harbor in St. Barths
$7,590
EXPLORE

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
Activities:
Small Ship Cruises, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Embark on an 8-day Caribbean cruise aboard Emerald Azzurra. Start in Marigot, Saint Martin, and board your luxury yacht. Cruise to Anguilla, known for its coral beaches and clear waters, and snorkel over vivid coral reefs. Visit Virgin Gorda to see the Baths, impressive granite grottoes formed by …
Cruise Details
0
Soufriere bay, St Lucia
$5,200
EXPLORE

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, Small Ship Cruises, Snorkeling
Activity Level:
Variable
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Bellot 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 garrison. Visit …
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
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
The crystal blue water of Jost van Dyke
$2,720
EXPLORE

Jamaica to Antigua

12 Day Itinerary aboard Star Clipper
  • Swim in Montego Bay's waters
  • Explore Santo Domingo
  • Visit the Treasure Island
  • Hike Virgin Gorda trails
Starts / Ends:
Port Antonio / St. John's
Activities:
Local Market Visits, Small Ship Cruises, Snorkeling, Spa Relaxation
Activity Level:
Variable
Embark on a 12-day Caribbean cruise adventure from Jamaica to Antigua aboard Star Clipper. Explore historical sites like Rose Hall Great House or enjoy activities like snorkeling and zip-lining. Visit Port Antonio, a charming town with lush landscapes, secluded beaches, and attractions like Blue …
Cruise Details
0
Relax on the shores of the Caribbean
$6,320
EXPLORE

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Vieux Fort - Fort-de-France - 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:
Land & Sea Exploration, Small Ship Cruises, Snorkeling
Activity Level:
Variable
Embark on a 9-day cruise through the Caribbean aboard Le Bellot, tailored for travelers seeking cultural immersion. Start in Vieux Fort, St. Lucia, and see the UNESCO-listed Gros and Petit Pitons. Sail to Portsmouth, Dominica, to explore landscapes and local chocolate. Continue to Les Saintes, …
Cruise Details
0
1-9 of 9 Results
TrustScore 4.9 | 306 reviews
TrustScore 4.9 of 5
total score
Based on 306 reviews on
review score
2 days ago
Tony and Shannon were always quick to answer my questions and requests. They booked my Upper Mississippi cruise perfectly. They made sure that my dietary needs were met which is a big deal for me. I have the utmost confidence with their assistance.
Code
review score
3 days ago
Third trip we have book with Adventure Life. Like the last two, we have had a quick response to all inquires
Carol Borland
review score
3 days ago
Angela was fantastic! She was thoughtful, helpful, and prompt in her responses without being intrusive. She accommodated our large group and was genuinely excited for us when it all worked out. Can't say enough good things! This is our second trip booking through Adventure Life and we will definitely do it again.
Emily
review score
4 days ago
Jessica was extremely helpful and generous with her time. She was very responsive to our questions and comments and in a very timely fashion. She worked with us in partnership to plan a trip specifically for us and our wants and needs.
Linda Coleman
review score
4 days ago
Mary Curry found right trip for my budget and the best date that I liked. She made that reservation when other company's agent could not do it. Thank you so much!
Theresa AN

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