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Famous colorful huts in Barbados

Windward Islands Cruises & Travel

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Choose from one of these sailing cruises or small ship cruises that will let you access the best of the Windward Islands' culture, wildlife, and of course, isolated beaches. Contact one of Adventure Life's Caribbean experts if you have any questions about traveling to the Windward Islands or anywhere else in the Caribbean.
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    • Windward Islands
The charming streets of Colonial Caribbean
$4,995
EXPLORE

Caribbean: Bridgetown to Bridgetown

8 Day Itinerary aboard Sea Cloud
  • Visit the famous Argyle Waterfall
  • Hike to the top of Morne Gazo
  • Snorkel & swim at Tobago Cays
  • Discover St Lucia Island
Activities: Hiking, Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Discover the treasures of the Grenadines! Enjoy majestic volcanoes, colorful reefs, and the scent of nutmeg and vanilla on this exclusive 8-day sailing adventure. VisitGrenada, the island of spice, and explore its deep volcanic lakes, dense rainforests, waterfalls, sugar cane fields, and spice …
Cruise Details
An underwater world awaits you
$3,000
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Antigua to Grenada

14 Day Itinerary aboard Mandalay
  • Discover Bequia's landscapes
  • Explore local bars and restaurants
  • Visit St. Lucia's beaches and reefs
  • Snorkel and swim from the boat
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
This 14-day cruise offers the best opoortunirty for a true sailing vessel journey. Board the S/V Mandalay in Antigua and disembark in Grenada. As the wind marks the navigation course visit islands like Nevis, Isle Des Saintes, Dominica, St. Lucia, St. Vincent, Bequia, Canouan, Tobago Cays, Mayreau, …
Cruise Details
The s/v Mandalay
$2,800
EXPLORE

Grenada Round Trip

14 Day Itinerary aboard Mandalay
  • Rise early & search for marine life
  • Snorkel in crystal-clear waters
  • Enjoy views of the night sky
  • Learn to raise the ship's sails
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Enjoy two weeks in the Southern Caribbean sailing on board the Mandalay. Sail through turquoise waters, watch for marinelife, and relax on white sand beaches as you escape to these remote islands. While onboard learn how to raise the sails, take a turn at the helm, or just relax on deck!
Cruise Details
Top Deck
$1,799
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Sail to St. Lucia

7 Day Itinerary aboard Mandalay
  • Enjoy morning coffee at sunrise
  • Snorkel & swim in Caribbean waters
  • Sip a rum swizzle
  • Relax on the top deck
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Join the S/V Mandalay crew on this 7-day roundtrip sailing adventure starting and ending in St. Lucia, an island known for its beaches and reef-diving sites. Enjoy the winds of the Caribbean, take a turn at the helm, and partake in raising the vessel sails. Experience daily island visits for …
Cruise Details
The beautiful Caribbean
$1,799
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St. Maarten to St. Lucia

7 Day Itinerary aboard Mandalay
  • View marine life and birds
  • Listen to local lore
  • Relax on Caribbean beaches
  • Taste local seafood
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
This 7-day adventure aboard the S/V Mandalay takes you from St. Maarten to St. Lucia for a memorable vacation in paradise. Swim, snorkel, and relax on golden beaches bathed in crystal-clear Caribbean waters. Visit a selection of islands including St. Maarten, Nevis, St. Kitts, Anguilla, Dominica, …
Cruise Details
Grenada at night - Mandalay
$1,599
EXPLORE

Sailing the Grenadines

7 Day Itinerary aboard Mandalay
  • Snorkel in crystal-clear waters
  • Enjoy Bloody Marys at sunrise
  • Partake in nightly activities
  • Rise early & search for marine life
Activities: Sailing Schooner, Snorkeling
Activity Level: Relaxed
Enjoy a week in the Southern Caribbean sailing the Grenadines on board the Mandalay. Cruise through turquoise waters, watch for marinelife, and relax on white sand beaches as you escape to these remote islands. While onboard learn how to raise the sails, take a turn at the helm, or just relax on …
Cruise Details
Mayreau Island, St Vincent and Grenadines
$6,900
EXPLORE

Bridgetown to Bridgetown via Bequia

8 Day Itinerary aboard SeaDream I
  • Explore unspoiled Canouan Island
  • Visit Union Island
  • Snorkel at Tobago Cays
  • Discover Mayreau
Activities: Biking, Helicopter Tour, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Enjoy some water sports, relax on one of the most beautiful beachesin the world, or hike through magical landscapes on this 8-day adventure sailing across the Caribbean. Visit Pigeon Island National Park, witness the ruins of military buildings, and discover the signature Caviar Splash and Beach …
Cruise Details
Sea turtle
$5,400
EXPLORE

Round-trip Bridgetown via St. Lucia

8 Day Itinerary aboard SeaDream I
  • Helicopter ride across St Lucia
  • Enjoy a catamaran ride to Mustique
  • Discover the Southern Grenadines
  • Kayak at Grande Anse
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Sun and sand are yours on this exceptional 8-day round-trip Barbados cruise. Begin your island journey in Bridgetown and make your way to the beautiful Rodney and Soufriere Bays, Port Elizabeth, and the stunning Canouan and Union Islands. Disembark daily to explore colorful markets and snorkel, …
Cruise Details
Snorkelling the warm waters
$8,640
Save 5%
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Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud (LI)
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
Activities: Sailing Schooner, Small Ship Cruise, 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
Snorkel the vibrant reef system
$6,900
EXPLORE

Round-trip Barbados

7 Day Itinerary aboard SeaDream I
  • Explore St. Lucia Island
  • Visit pristine Canoaun Island
  • Snorkel & swim at Tobago Cays
  • Sail along the coast of Mustique
Activities: Fishing, Helicopter Tour, Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Discover the treasures of the Grenadines! Enjoy majestic volcanoes, colorful reefs, and the scent of nutmeg and vanilla on this magical 7-day sailing adventure. Scout around the snorkelers’ paradise of Tobago Cays; this horseshoe-shaped coral reef encloses four small islands that glow in rich …
Cruise Details
Promenade in Bridgetown, Barbados
$7,695
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Caribbean: Round-trip Bridgetown

15 Day Itinerary aboard Sea Cloud
  • Visit Cabrits National Park
  • Enjoy the magical Argyle Waterfall
  • Discover Bequia's turtle sanctuary
  • Snorkel at Tobago Cays
Activities: Hiking, Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Experience the blue waters of the wonderful Caribbean on this 15-day round-trip cruise from Barbados. As you sail, visit the charming port cities and remote coves of Tobago Cays, Soufriere, Cabrits, and more. The Caribbean is a vibrant, lively region of colorful buildings and friendly locals. Fall …
Cruise Details
A view off the beautiful coast of Madeira.
$5,400
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Bridgetown to Lisbon

13 Day Itinerary aboard SeaDream I
  • Sit back and relax on board
  • Discover the tranquility offshore
  • Sample wine at Funchal, Madeira
  • Enjoy perfect views of Lisbon
Activities: Small Ship Cruise, Urban Exploration, Wine Tasting
Activity Level: Relaxed
Crossing the Atlantic in a small ship is an experience that leaves a lasting impression. For 13 days sail across the Atlantic Ocean, making your way from Barbados to the enchanting city of Lisbon. Sit back and relax, surrounded by vast horizons and perfect tropical weather conditions as you leave …
Cruise Details
Anses d'Arlet village, Martinique, West Indies
$9,595
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Caribbean: Round-trip Bridgetown 2017

15 Day Itinerary aboard Sea Cloud II
  • Enjoy luxurious St. Barts
  • Discover the ÎIes des Saintes
  • Snorkel the Tobago Cays
  • Visit Grenada, the island of spice
Activities: Sailing Schooner, Snorkeling
Activity Level: Relaxed
Spend the holidays on thisunforgettable 15-day cruise exploring Caribbean hotspots. Enjoy stunning volcanic sceneries and island hideaways on the sunny side of the Lesser Antilles and the Grenadines. Discover the unique charm of this exclusive region - with more than 60 islands and reefs (of which …
Cruise Details
Coconut Grove, Nevis Island
$7,900
EXPLORE

Marigot to Bridgetown

9 Day Itinerary aboard SeaDream I
  • Zip-line on St. Martin
  • Discover Iles des Sainte
  • Hike through Nevis Island
  • Explore the unique Spice Islet
Activities: Biking, Fishing, Helicopter Tour, Hiking, Horseback Riding, Kayaking, Small Ship Cruise, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Enjoy a little bit of everything on this amazing 9-day cruise, starting at Saint Martin and sailing to beautiful Barbados. Visit the famous jet set island of St.Barts, well known for its charming streets, glamorous cafes and restaurants, and luxury white sand beaches. Explorethe capital of Grenada, …
Cruise Details
The Pitons of St. Lucia
$12,980
EXPLORE

Hidden Gems of the Caribbean

12 Day Itinerary aboard Le Ponant (ZE)
  • Visit little-explored Grenadines
  • Seek out a variety of endemic birds
  • Snorkel or dive to discover reefs
  • Learn the history of the islands
Activities: Hiking, Scuba Diving, Snorkeling, Village Visit, Wildlife Viewing
Activity Level: Relaxed
Explore the lesser-known island gems of the eastern Caribbean on an itinerary exclusively designed to take you far from the standard cruise ship routes. Join Le Ponant on this 12-day journey, discovering several of the idyllic islands thatcomprise the little-explored Grenadines, an island chain in …
Cruise Details
Famous colorful huts in Barbados
$10,900
EXPLORE

Bridgetown to Marigot

10 Day Itinerary aboard SeaDream I
  • Hike through beautiful Saba
  • Participate in the America's Cup
  • Enjoy an extreme Marigot zip-line
  • Kayak and discover Les Saintes
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Enjoy the Caribbean's famous and perfect tropical weather on this incredible 10-day cruise from Bridgetown to Marigot. Visit picturesque Palm Island, and discover its small town delights whilst doing some shopping for local crafts, souvenirs, or tropical fruits, jams, jellies or preserves. …
Cruise Details
Scuba diving in the reefs
$6,900
EXPLORE

Marigot to Bridgetown via Guadeloupe

8 Day Itinerary aboard SeaDream I
  • Discover St. Lucia
  • Visit the Moon Hole at Bequia
  • Relax at Mustique
  • Experience Iles des Saintes
Activities: Fishing, Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
This unique cruise mixes relaxation and adventure perfectly! Explore the Caribbeanwhile you enjoy incredible views of the islands on this 8-day expedition aboard the SeaDream I. VisitPort Elizabeth, well known for its reefs and long silvery stretches of beach. Among the first things you notice are …
Cruise Details
Le Marin, Martinique
$6,900
EXPLORE

Bridgetown to Marigot

6 Day Itinerary aboard SeaDream I
  • Hike at Chevalier Islet
  • Explore Les Saintes by kayak
  • Enjoy a horseback ride on Nevis
  • Snorkel among colorful marine life
Activities: Fishing, Hiking, Horseback Riding, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing, Zip Line
Activity Level: Relaxed
Sail across the Caribbean on this exclusive 6-day adventure. Indulge yourself with paradisical beaches full of history and tropical warm temperatures. Stroll along picturesque streets full of colonial houses standing beside smart cafés and bistros, pastry shops and luxury boutiques at St. …
Cruise Details
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