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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
Promenade in Bridgetown, Barbados
$4,400
EXPLORE

Bridgetown to Bridgetown

5 Day Itinerary aboard SeaDream I
  • Enjoy the fresh breeze on deck
  • Discover Clifton Bay's local crafts
  • Explore \\"The Moon Hole”
Activities: Fishing, Hiking, Snorkeling
Activity Level: Relaxed
Spend some time exploring the Caribbean on this 5-day sailing adventure. Enjoy a slow panoramic ride alongBequia'scoast while a knowledgeable guide points out where the luxurious houses of the rich and famous can be seen including Ralph Lauren and Sir Paul McCartney. Discover an intimate …
Cruise Details
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
The Pitons of St. Lucia
$4,295
EXPLORE

Caribbean: Round-trip Bridgetown 2017

8 Day Itinerary aboard Sea Cloud II
  • Explore the Argyle Waterfall
  • Discover Grenada Island
  • Swim in the Tobago Cays
  • Visit Old Hegg Turtle Sanctuary
Activities: Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Start off the New Year in the laid-back Caribbean and discover the pearls of the Lesser Antilles and the Grenadines. Start your adventure atBridgetown, Barbados and srtoll down its historic center, with colonial architecture surrounding Trafalgar Square. VisitGrenada, a paradisiacal spotblessed …
Cruise Details
Snorkel the clear, tropical waters
$3,000
EXPLORE

Grenada to St. Maarten

14 Day Itinerary aboard Mandalay
  • Enjoy tours through local villages
  • Visit the small island of Mayreau
  • Snorkel with sea turtles
  • Partake in raising the sails
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level: Relaxed
This 14-day adventure takes you from Grenada to St. Maarten aboard the S/V Mandalay, a true sailing vessel that currently navigates through the Windward and Leeward islands. Begin your sailing adventure in Grenada, known as the "Island of Spice" because of the abundance of locally grown …
Cruise Details
An underwater world awaits you
$3,000
EXPLORE

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
Mandalay Caribbean Beach
$3,000
EXPLORE

British Virgin Islands

14 Day Itinerary aboard Mandalay
  • Discover the "Island of Spice"
  • Rest on Bequia's beaches
  • Snorkel and swim at Mayreau
  • View turtles in their habitat
Activities: Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level: Relaxed
This 14-day exploration of theBritish Virgin Islands includes visits to magnificent bays,inhabited islands, and crystal clear waters. Enjoy snorkeling opportunities andsoak up the sun on beautiful Caribbean sandy beaches. Take part in raising the sails or just enjoy the sea winds as you navigate …
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
The beautiful Caribbean
$1,799
EXPLORE

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
Top Deck
$1,799
EXPLORE

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
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
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
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
Famous colorful huts in Barbados
$3,795
EXPLORE

Caribbean: Round-trip Bridgetown 2016

8 Day Itinerary aboard Sea Cloud II
  • Travel to the Argyle Waterfall
  • Snorkel & swim at Tobago Cays
  • Visit botanical gardens
  • Discover Gros and Petit Piton
Activities: Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level: Relaxed
Join the Sea Cloud II on this 8-day cruise discovering Caribbean hot spots. Enjoy exclusive picture-perfect beaches, deep volcanic lakes, dense rainforests, amazing waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. …
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
EXPLORE

Caribbean: Round-trip Bridgetown 2016

15 Day Itinerary aboard Sea Cloud II
  • Visit Cabrits National Park in Domi
  • 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 Man-o-War Bay, Tobago Cays, Soufriere, Cabrits, and more. The Caribbean is a vibrant, lively region of colorful buildings and …
Cruise Details
A view off the beautiful coast of Madeira.
$5,400
EXPLORE

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
EXPLORE

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
White Sand Beach in Barbados
$8,400
EXPLORE

Bridgetown to Bridgetown

11 Day Itinerary aboard SeaDream I
  • Discover the Grande Anse mangrove
  • Explore the Sapphire Waterfall
  • Kayak the waters of Les Saintes
  • Snorkel at St. Barts
Activities: Helicopter Tour, Hiking, Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level: Relaxed
Discover the many facets of the Caribbean on this exclusive 11-day expedition. Enjoy Terre-de-Haut, one of the most picturesque spots in the entire archipelago. Stroll along charming streets and colorfully painted houses while you soak in the relaxed blend of the islands. Visit Gustavia, an …
Cruise Details
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