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Relax on the beaches of the Caribbean

Leeward Islands Cruises Tours in 2025

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Embark on a voyage to the enchanting Leeward Islands with our 17 distinctive tours scheduled for 2025. The Leeward Islands, a mesmerizing archipelago where the Caribbean Sea dances with the Atlantic Ocean, offers a symphony of experiences for the discerning traveler. From the geological wonder of Virgin Gorda's "Baths" to the historic allure of Basseterre's streets, each island sings its own unique melody. Over the course of 8 to 25 days, you will have the opportunity to indulge in small ship sailing, immerse yourself in the vibrant local culture, and snorkel in the crystal-clear waters that bathe these sun-kissed shores. With a starting point of $1,870, set sail on a journey that promises relaxation and discovery in equal measure. To weave the vibrant tapestry of the Leeward Islands into your travel story, contact one of Adventure Life's Caribbean specialists for help planning your next seamless trip.
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    • Leeward Islands
Enjoy a Caribbean escape
from $3,980
EXPLORE

Save the Best for Last

Roundtrip St. Maarten - 8 Day Itinerary aboard Sea Cloud
  • Discover The Baths
  • Relax at Bitter End
  • Sail to Jost van Dyke
  • Experience St. Barths
  • Explore Nevis
Starts / Ends
Philipsburg / St. Martin
Activities
Small Ship Sailing
Activity Level
Variable
Sail aboard the Sea Cloud on a 10-day Caribbean adventure through the British Virgin Islands, St. Barths, Nevis, and St. Maarten. Explore Virgin Gorda’s iconic Baths, unwind at the Bitter End Yacht Club, and sail the Sir Francis Drake Channel to Jost van Dyke. Stroll St. Barths’ luxury shops, discover Nevis’ lush rainforests, and end in vibrant Philipsburg.
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest
from $1,960
SS 25%
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
Activity Level
Variable
Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!
Cruise Details
0
St Barts harbor view
from $7,990
2-for-1
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Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Barbuda's pink beaches
  • Discover Deshaies’ architecture
  • Visit Gustavia’s charming boutiques
  • Experience Virgin Gorda’s baths
Starts / Ends
St. John's / San Juan
Activities
Local Market Visits, Hiking, Urban Exploration
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
Cruise Details
0
Soak in the sun in colorful Marigot
from $10,670
2-for-1
EXPLORE

Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Sakara
  • Dive in Anguilla
  • Explore Virgin Gorda
  • Discover Anegada
  • Experience Jost van Dyke
Starts / Ends
Marigot / Marigot
Activity Level
Variable
Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning destinations, immersing yourself in picturesque landscapes, vibrant cities, and unique natural wonders.
Cruise Details
0
Relax on the beaches of St. Maarten
from $1,870
SS 25%
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
Activity Level
Variable
The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.
Cruise Details
0
Dock going out into the crystal blue ocean
from $2,020
EXPLORE

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
0
Explore the famous rock formations of the baths
from $5,245
EXPLORE

A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Old San Juan's forts
  • Enjoy salsa music
  • Sail in the British Virgin Islands
  • Explore unique rock formations
Starts / Ends
San Juan / San Juan
Activity Level
Variable
Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and salsa-filled cafes. Discover UNESCO-listed sites like La Fortaleza and Fort San Felipe del Morro, resonating with centuries of history and cultural vibrancy.
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $7,590
2-for-1
EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara
  • Experience Falmouth's historic port
  • Discover Soufriere's Sulphur Spring
  • Visit Falmouth Harbour in Antigua
  • Explore Nelson’s Dockyard
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbour’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise
Cruise Details
0
Explore colorful Gustavia
from $8,390
2-for-1
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara
  • Explore Bridgetown's culture
  • Stroll Gustavia's colorful streets
  • Admire Marigot’s scenic coastline
  • Savor Soufriere's delicious cuisine
Starts / Ends
Bridgetown / Marigot
Activities
Wildlife Viewing
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
Cruise Details
0
Pink beach huts in the Caribbean
from $2,020
EXPLORE

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
0
Soufriere bay, St Lucia
from $5,520
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
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
0
White Sand Beach in Barbados
from $2,020
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
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
0
Enjoy the beautiful blue Caribbean
from $21,340
2-for-1
EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Experience Falmouth's historic port
  • Discover Soufriere's Sulfur Spring
  • Visit Falmouth Harbour in Antigua
  • Explore Nelson’s Dockyard
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
Relax on the shores of the Caribbean
from $15,180
2-for-1
EXPLORE

Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara
  • Experience Falmouth's historic port
  • Discover Soufriere's Sulfur Spring
  • Visit Falmouth Harbour in Antigua
  • Explore Nelson’s Dockyard
Starts / Ends
Bridgetown / Marigot
Activities
Snorkeling, Village Visits
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
Beautiful beach in Dominica
from $8,370
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
Activity Level
Variable
Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint Vincent and the Grenadines, snorkeling in Tobago Cays' clear waters. Experience sunsets, local culture, and beaches in Marie-Galante. This cruise combines relaxation and adventure in the Caribbean.
Cruise Details
0
The vivid colors of the San Blas Islands
from $4,350
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Explore Balboa’s colonial charm
  • Transit Panama’s iconic canal
  • Discover San Blas culture
  • Enjoy Aruba’s clear waters
Starts / Ends
Balboa / St. John's
Activities
Archaeological Site Visits
Activity Level
Variable
Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.
Cruise Details
0
Explore the beautiful Canary Islands
from $4,820
EXPLORE

Westbound Atlantic Ocean Crossing

25 Day Itinerary aboard Star Flyer
  • Discover the Rock of Gibraltar
  • Experience Tangier
  • Visit Cadiz
  • Explore Safi
Starts / Ends
Malaga / Philipsburg
Activity Level
Variable
Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.
Cruise Details
0
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