Have questions? We're here.
Vivid blue waters of the Caribbean

Windward Islands Small Ship Cruises

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Experience the wonders of the Windward Islands in the Caribbean with Adventure Life's array of 20 small ship cruises for 2024. Join us on a cruise journey through the vibrant archipelago, from snorkeling in the pristine waters to relaxing on blissful beaches. Delight your senses with the unique aromas of Grenada, taste the spicy Creole cooking, and explore lush islands like St. Lucia and ÎIes des Saintes. From swimming amidst marine life to observing UNESCO World Heritage sites, each moment offers a chance to immerse yourself in the rich culture and natural beauty of the region. With activities like snorkeling, wildlife viewing, and beach explorations, this adventure is perfect for travelers seeking a relaxed pace and unforgettable experiences. Don't miss the opportunity to set sail on a unique Caribbean voyage and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (20 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Windward Islands
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:
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
0
Dock going out into the crystal blue ocean
$1,700
EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Enjoy Grenada's unique aromas
  • Discover Falmouth Harbour, Antigua
  • Enjoy the beach in ÎIes des Saintes
  • Explore lush St. Lucia Island
Starts / Ends:
St. John's / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Swim and snorkel amidst the beautiful, pristine waters of the Caribbean Sea on this 8-day expedition aboard Royal Clipper. Sail away from your everyday life and find tropical bliss in the islands. From the stunning drama of the spectacular Pitons at St. Luciato the captivating charm of Les Saintes, …
Cruise Details
0
Pelicans hanging out in the ocean
$11,830
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
0
Take a leisurely stroll through beautiful Bridgetown
$2,550
EXPLORE

Eastbound Atlantic Ocean Crossing

15 Day Itinerary aboard Royal Clipper
  • Explore the east coast of Barbados
  • Discover Santa Cruz
  • Experience Las Palmas
  • Visit Caldera de Bandama
Starts / Ends:
Bridgetown / Las Palmas
Activities:
Small Ship Cruises
Activity Level:
Relaxed
Join the Royal Clipper on a 15-day cruise departing from Bridgetown, Barbados. Experience the vibrant contrasts of this coastal town, with its red-sand beaches and lively streets. Explore the British-influenced heritage through landmarks like Trafalgar Square and discover traditions like cricket …
Cruise Details
0
St George's Harbor - Grenada
$5,430
EXPLORE

Pearls of the Caribbean

9 Day Itinerary aboard Le Champlain
  • 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:
Hiking, Kayaking, Small Ship Cruises, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Champlain on its 9-day cruise combining long, white-sand beaches and the easy 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
Play on the famously beautiful beaches of St. Barth's
$11,595
EXPLORE

Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb - 15 Day Itinerary aboard Sea Cloud
  • Snorkel the famed Virgin Gorda
  • See luxurious St. Barthelemy
  • Explore the culture of Grenada
  • Admire beautiful St. Lucia
Starts / Ends:
Philipsburg / St. Barth
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Explore the best of the Caribbean on this round-trip cruise from Philipsburg aboard the Sea Cloud sailing ship. From the charming Dutch Colonial port town of Philipsburg, make your way to the British Virgin Islands. Snorkel the famed baths, or simply relax on the white sandy beaches before sailing …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$3,540
EXPLORE

Barbados to Panama Christmas Cruise

15 Day Itinerary aboard Star Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts / Ends:
Bridgetown / Balboa
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Star Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
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:
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 …
Cruise Details
0
Boats Moored to the Quay at Bridgetown Harbour
$4,440
EXPLORE

Barbados to Panama

15 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts / Ends:
Bridgetown / Balboa
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Stroll along the beautiful beaches of the Caribbean
$8,150
EXPLORE

The Essential of the Caribbean

Fort-de-France Roundtrip - 13 Day Itinerary aboard Le Champlain
  • Cruise in West Indies
  • Visit heritage sites
  • Discover British Virgin Islands
  • Private beach day in Mayreau
Starts / Ends:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Variable
You begin your voyage in St. Kitts, a volcanic island known for its excellent sandy beaches and rich colonial history. Your cruise then docks in Anguilla before continuing west to the British Virgin Islands, which have gorgeous landscapes. Then, sail to Saint Barthelemy and the enchanted setting of …
Cruise Details
0
Enjoying the landscape of Lencois Maranhenses National Park
$10,680
Savings
EXPLORE

Exploring South America

Barbados - Brazil - 21 Day Itinerary aboard SH Vega
  • Explore the Amazon Rainforest
  • Visit Georgetown and Paramaribo
  • Explore Lençóis Maranhenses
  • Explore cultures and wildlife
Starts / Ends:
Bridgetown / Salvador
Activities:
Adventure Options, Archaeological Site Visits, Small Ship Cruises, Wildlife Viewing
Activity Level:
Variable
Embark on a 21-day cruise aboard SH Vega and explore the Atlantic coastline of South America. The adventure takes you from Barbados to Brazil, where you discover the wonders of this diverse region. During the trip, you encounter the rich biodiversity of the Amazon Rainforest, explore the colonial …
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:
Relaxed
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
Gatun Lock of the Panama Canal
$4,440
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Transit the historic Panama Canal
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Swim in paradise in Bonaire
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Amazon River
$26,199
EXPLORE

Wild Guianas to the Amazon Basin

15 Day Itinerary aboard Seabourn Venture
  • Discover Port-of-Spain
  • Explore Bridgetown
  • Experience Paramaribo
  • Witness Devil's Island
Starts / Ends:
Bridgetown / Manaus
Activities:
Hiking, Small Ship Cruises
Activity Level:
Relaxed
Embark on a 15-day cruise aboard the Seabourn Venture. Discover the Caribbean and Amazon starting in Bridgetown, Barbados, boasting British heritage and serene coastlines. Explore Trinidad and Tobago's cultural blend or Caroni Swamp's sunset spectacle. Continue to Suriname's Paramaribo, …
Cruise Details
0
Nassau Lighthouse
$23,390
2for1
EXPLORE

Island Odyssey: Bahamas to the Grenadines

Nassau - Bridgetown - 13 Day Itinerary aboard Scenic Eclipse
  • Explore beaches on Compass Cay
  • See swimming pigs on Exuma Island
  • Discover Long Island on foot
  • Enjoy the view from Gorda Point
Starts / Ends:
Nassau / Bridgetown
Activities:
Hiking, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Embark on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Sail to Compass Cay and explore its pristine beaches, snorkel in crystal-clear waters, or spot marine life from the marina. Discover the hidden gem of Great Exuma Island, with its …
Cruise Details
0
The stunning blue coastline of the Canary Islands
$2,490
EXPLORE

Westbound Atlantic Ocean Crossing

Las Palmas to Barbados - 16 Day Itinerary aboard Star Flyer
  • Visit Las Palmas, Gran Canaria
  • Take in the fresh ocean breeze
  • Explore San Sebastian, La Gomera
  • Relax on paradise beaches
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Crossing the mighty Atlantic Ocean provides the time to truly appreciate the pure pleasure of the sea. Imagine sailing the Atlantic in the footsteps of legendary explorers, enjoying the Old World family charm and the wonders of the New World. Admire Gran Canaria's exotic vegetation and magical …
Cruise Details
0
The stunning blue coastline of the Canary Islands
$2,490
EXPLORE

Transatlantic: Las Palmas to Barbados

16 Day Itinerary aboard Star Clipper
  • Visit Las Palmas, Gran Canaria
  • Take in the fresh ocean breeze
  • Explore San Sebastian, La Gomera
  • Relax on paradise beaches
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Crossing the mighty Atlantic Ocean provides the time to truly appreciate the pure pleasure of the sea. Imagine sailing the Atlantic in the footsteps of legendary explorers, enjoying the Old World family charm and the wonders of the New World. Admire Gran Canaria's exotic vegetation and magical …
Cruise Details
0
Take in the sights, sounds, and colors of Barbados
$6,240
EXPLORE

Westbound Atlantic Ocean Crossing

Cannes to Barbados - 29 Day Itinerary aboard Royal Clipper
  • Marvel at Bonifacio's views
  • Explore charming Mahon, Menorca
  • See Malaga's Moorish architecture
  • Enjoy Marbella's natural beauty
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Experience the uninhibited thrill of traversing a boundless ocean under sail, without any skills or effort required on your part. Imagine long lazy days at sea chasing the horizon, relaxing under a blanket of stars, and taking in the ocean's salty fragrance. Embarking in the city of Cannes, …
Cruise Details
0
1-18 of 20 Results

Caribbean Travel Guide

Favorite Caribbean All Trips

Top Windward Islands Travel Destinations

Windward Islands Trips by Departure Date

Windward Islands Trips by Duration

Windward Islands Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By