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Top Windward Islands Tours & Cruises in 2025

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Discover the best the world has to offer with Adventure Life’s expert-curated Windward Islands tours 2025. From Bridgetown, Soufriere, Tobago Cays, Bequia, and St. Georges to hidden gems off the beaten path, our 21 top-rated itineraries take you deep into Windward Islands’s breathtaking landscapes. Guided by bilingual experts, these immersive experiences cater to adventurers seeking unique journeys in small groups or customizable private tours.

Choose from a variety of 8 to 29 days itineraries starting at $1,960 to $61,680. You’ll find options that suit your travel style. Whether you’re passionate about Small Ship Sailing, Archaeological Site Visits, Snorkeling, Local Market Visits, and Village Visits or eager to explore Windward Islands’s rich culture and natural beauty, our Windward Islands tours 2025 deliver unforgettable moments. Each itinerary blends awe-inspiring exploration with a commitment to sustainability to ensure your adventure supports the preservation of our planet.

Adventure Life’s dedication to personalized travel promises your Windward Islands tour 2025 is seamless from start to finish. From arranging transportation to selecting accommodations tailored to your preferences, we’ll take care of every detail. Our expert recommendations and insider tips make your journey even more enriching.

Contact our specialists today to start planning your Windward Islands tour 2025. Whether you’re a solo traveler, a couple, or part of a group, Adventure Life will create a transformative experience you’ll treasure forever.
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    • Windward Islands
Take a leisurely stroll through beautiful Bridgetown
from $8,390
2for1
EXPLORE

Grenadines & Windwards Yachting

Roundtrip Bridgetown - 8 Day Itinerary aboard Emerald Sakara
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Embark on an 8-day cruise aboard the Emerald Sakara, starting and ending in Bridgetown, Barbados. Explore historic towns, relax on stunning beaches, and enjoy snorkeling and water activities in the picturesque Saint Vincent and the Grenadines.
  • Discover Bequia’s secluded beaches
  • Savor Caribbean dining experiences
  • Snorkel Tobago Cays' waters
  • Admire panoramic views from Mayreau
Cruise Details
0
White Sand Beach in Barbados
from $2,020
EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper
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.
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Cruise Details
0
Explore colorful Bridgetown, Barbados
from $6,200
EXPLORE

Bridgetown to Bridgetown

8 Day Itinerary aboard Silver Spirit
Starts / Ends
Bridgetown / Bridgetown
Activities
Small Ship Sailing, Wildlife Viewing, Local Market Visits, Archaeological Site Visits, Spa Relaxation
Activity Level
Variable
Embark on an 8-day Caribbean round-trip cruise from Bridgetown aboard the Silver Spirit. Explore some of the most iconic and lesser-known islands in the region, including Saint Lucia, Martinique, Saint Barthelemy, Dominica, Grenada, and Bequia. Each destination offers unique cultural experiences, breathtaking natural beauty, and vibrant local life.
  • Hike to Saint Lucia’s Pitons
  • Snorkel Martinique’s colorful reefs
  • Explore Gustavia’s historic harbor
  • Stroll Bequia’s scenic shores
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
Starts / Ends
St. John's / Bridgetown
Activities
Hiking
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.
  • Explore Antigua’s vibrant dockyards
  • Discover Les Saintes’ beaches
  • Relax on Martinique’s white sands
  • Stroll Grenada’s aromatic markets
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
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.
  • Enjoy iconic pitons of Saint Lucia
  • Learn about Kalinago culture
  • Explore Tobago Cays' coral reefs
  • Relax on Marie-Galante's beaches
Cruise Details
0
Relax on the shores of the Caribbean
from $15,180
2for1
EXPLORE

Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara
Starts / Ends
Bridgetown / Marigot
Activities
Village Visits, Snorkeling, Kayaking
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.
  • Explore Bridgetown’s capital
  • Wander Speightstown’s streets
  • Discover Kingstown’s gardens
  • Unwind on Bequia Island
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
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!
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Cruise Details
0
Enjoy the beautiful blue Caribbean
from $21,340
2for1
EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
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.
  • Explore Anguilla’s turquoise waters
  • Stroll through Gustavia
  • Admire Nevis’ tranquil shores
  • Visit Antigua’s Falmouth Bay
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
from $4,350
EXPLORE

Barbados to Panama

15 Day Itinerary aboard Royal Clipper
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Cruise Details
0
Pink beach huts in the Caribbean
from $2,020
EXPLORE

Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper
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.
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Cruise Details
0
The vivid colors of the San Blas Islands
from $4,240
EXPLORE

Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.
  • Explore Bridgetown’s heritage
  • Discover St. George’s coastal views
  • Admire Kralendijk’s marine life
  • Wander Willemstad’s streets
Cruise Details
0
Explore colorful Gustavia
from $8,390
2for1
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara
Starts / Ends
Bridgetown / Marigot
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.
  • Explore Soufriere coral reefs
  • Visit Iles des Saintes towns
  • Discover Falmouth Harbor dockyard
  • Experience Charlestown’s Nevis
Cruise Details
0
Enjoying the landscape of Lencois Maranhenses National Park
from $21,580
Air Credit
EXPLORE

Exploring South America

Barbados - Brazil - 21 Day Itinerary aboard SH Vega
Starts / Ends
Bridgetown / Salvador
Activities
Adventure Options
Activity Level
Variable
On this 21-day Exploring South America Cruise from Barbados to Brazil aboard SH Vega, explore South America's Atlantic coast from Barbados to Brazil, encountering the Amazon Rainforest's biodiversity, colonial history in cities like Georgetown and Paramaribo, and natural wonders like Lençóis Maranhenses and the Amazon River mouth.
  • Explore the Amazon Rainforest
  • Visit Georgetown and Paramaribo
  • Explore Lençóis Maranhenses
  • Explore cultures and wildlife
Cruise Details
0
Relax on the beaches of St. Maarten
from $1,960
Upgrade
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
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.
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $8,390
2for1
EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara
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 Harbor’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
  • Discover Anguilla’s coral coast
  • Explore Gustavia’s boutiques
  • Wander Nevis seaside buildings
  • Visit Antigua’s English Harbor
Cruise Details
0
The vivid colors of the San Blas Islands
from $4,350
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
Starts / Ends
Balboa / St. John's
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.
  • Explore Balboa’s colonial charm
  • Transit Panama’s iconic canal
  • Discover San Blas culture
  • Enjoy Aruba’s clear waters
Cruise Details
0
Enjoy the clear blue waters of the Canary Islands
from $4,610
EXPLORE

Westbound Atlantic Ocean Crossing

Malaga - Bridgetown - 25 Day Itinerary aboard Star Clipper
Starts / Ends
Malaga / Bridgetown
Activity Level
Variable
Embark on a 25-day cruise aboard the Star Clipper, exploring Spain, Morocco, and the Canary Islands before heading to Barbados. Experience diverse cultures, stunning landscapes, and relaxation at sea on this unforgettable journey.
  • Explore Malaga’s Moorish Alcazaba
  • Discover Tangier’s culture
  • Wander Cadiz’s palm-lined streets
  • Visit Safi’s old town
Cruise Details
0
The stunning blue coastline of the Canary Islands
from $2,720
EXPLORE

Westbound Atlantic Ocean Crossing

16 Day Itinerary aboard Star Clipper
Starts / Ends
Las Palmas / Bridgetown
Activity Level
Variable
Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage to the stunningly beautiful Caribbean Islands.
  • Visit Las Palmas, Gran Canaria
  • Take in the fresh ocean breeze
  • Explore San Sebastian, La Gomera
  • Relax on paradise beaches
Cruise Details
0
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