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Wander the white-sand beaches of St. Johns on your Virgin Islands cruise

Sailboat Cruises in Lesser Antilles

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Experience the Caribbean's rich tapestry of vibrant cultures and stunning landscapes with Adventure Life's array of 36 small ship sailing tours. Sail away to lesser-known ports and hidden gems on the sea, from the historic Bridgetown in Barbados to the lush island of St. Lucia and the charming Martinique. Swim and snorkel amidst the pristine waters, discover the Dutch colonial charm of Curacao, and witness the breathtaking beauty of the Pitons in St. Lucia. Whether you're exploring sophisticated Martinique or relaxing on the famous beaches of St. Barts, each moment offers a unique opportunity to immerse yourself in the wonders of the Caribbean. Engage in snorkeling, wildlife viewing, and island-hopping cruises that will fill your days with adventure and relaxation. With prices starting at $2,010 to $24,855, begin your Caribbean adventure today and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Lesser Antilles
Pink beach huts in the Caribbean
from $2,080
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
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Bright blue waters of the Caribbean
from $2,880
EXPLORE

Aruba to Grenada

Oranjestad - St. George - 11 Day Itinerary aboard Star Clipper
  • Visit Oranjestad to see beaches
  • See Willemstad gabled houses
  • Tour Curacao inland cunucu
  • Swim Charlestown Bay
Starts / Ends
Oranjestad / St. Georges
Activity Level
Variable
Set sail on an 11-day Caribbean cruise aboard the Star Clipper from Aruba to Grenada, exploring vibrant destinations like Oranjestad and Willemstad. Enjoy highlights such as snorkeling in Tobago Cays and visiting St. George’s and its historic sites in Grenada.
Cruise Details
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White Sand Beach in Barbados
from $2,080
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
Dock going out into the crystal blue ocean
from $2,080
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
Relax on the beaches of St. Maarten
from $2,010
EXPLORE

Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Explore Nevis sugar plantations
  • Visit Dominica boiling lakes
  • Snorkel Terre-de-Haut blue waters
  • Swim South Friars Bay clear waters
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest of Dominica
from $2,010
EXPLORE

Treasure Islands

St. Maarten Roundtrip - 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
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Tropical waterfall and turquoise pool in lush forest of Dominica
from $7,995
OBC $200
EXPLORE

Caribbean Flair Away from the Everyday

St. Maarten Roundtrip - 9 Day Itinerary aboard Sea Cloud Spirit
  • Visit historic Saint-Pierre ruins
  • Watch the crew hoist the sails
  • Snorkel the clear Tobago Cays
  • Explore St. Lucia's twin Pitons
  • Wander through Charlestown, Nevis
Starts / Ends
Philipsburg / St. Martin
Activities
Village Visits
Activity Level
Variable
Embark on a 9-day Caribbean cruise aboard the Sea Cloud Spirit. You depart from St. Maarten and visit Martinique, the Tobago Cays, St. Lucia, Dominica, and Nevis, then explore historic ruins, volcanoes, and reefs.
Cruise Details
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St. George's harbor in Grenada, where historic cannons overlook scenic ocean views and colorful hillside estates
from $7,995
OBC $200
EXPLORE

More Time for Island Dreams

St. Maarten Roundtrip - 9 Day Itinerary aboard Sea Cloud Spirit
  • Discover Terre-de-Haut
  • Snorkel Tobago Cays
  • Discover Grenada’s spices
  • Spot flamingos in Bonaire
  • Explore historic Willemstad
Starts / Ends
Philipsburg / Willemstad
Activities
Snorkeling, Small Ship Sailing, Wildlife Viewing
Activity Level
Variable
Experience a 9-day Caribbean cruise aboard the Sea Cloud Spirit. Depart from St. Maarten and sail to stunning destinations including Îles des Saintes, St. Lucia, the Tobago Cays, Grenada, and Bonaire before disembarking in Curaçao. Enjoy historic ports, coral reefs, and volcanic landscapes along the journey.
Cruise Details
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Learn about the history of the Caribbean
from $6,995
EXPLORE

Across A Sea Of Idyllic Islands

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore St. Maarten’s cultures
  • Visit Virgin Gorda’s Baths
  • Discover Jost van Dyke
  • Wander Gustavia, St. Barths
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit through the Caribbean’s Lesser Antilles & Grenadines. Discover St. Maarten, Virgin Gorda, Jost van Dyke, Norman Island, St John’s, and St. Barths while enjoying authentic tall-ship sailing and idyllic island scenery.
Cruise Details
0
View of Mount Pelée overlooking Saint-Pierre, northwest Martinique, French Caribbean island
from $6,995
EXPLORE

Sun-Drenched Sailing Days

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Philipsburg beaches
  • Visit Saint-Pierre ruins
  • Uncover St. Lucia’s Pitons
  • Discover Dominica’s jungle
Starts / Ends
Philipsburg / Philipsburg
Activities
Rainforest Exploration
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit through the Caribbean, Lesser Antilles & Grenadines. You explore St. Maarten, Martinique, St. Lucia, Dominica, Nevis, and Anguilla, combining colonial towns, volcanic peaks, rainforests, and white-sand beaches with authentic sailing experiences at sea.
Cruise Details
0
Soufriere bay, St Lucia
from $6,495
EXPLORE

Relax The Caribbean Way

Roundtrip Bridgetown - 8 Day Itinerary aboard Sea Cloud II
  • Snorkel in the Tobago Cays
  • Discover Grenada’s spices
  • Explore Saint-Pierre, Martinique
  • View Gros and Petit Piton
Starts / Ends
Bridgetown / Bridgetown
Activities
Stand Up Paddle Boarding
Activity Level
Variable
Experience an 8-day voyage aboard Sea Cloud II roundtrip from Bridgetown, Barbados, through the Lesser Antilles & Grenadines. You snorkel in the Tobago Cays, explore spice-rich Grenada, visit Saint-Pierre in Martinique, admire St. Lucia’s Pitons, and enjoy Caribbean sunsets at sea.
Cruise Details
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St. George's, Grenada's charming capital city known for having the most beautiful harbor in the Caribbean.
from $3,150
EXPLORE

Grenada Roundtrip

Roundtrip St George - 12 Day Itinerary aboard Star Clipper
  • Tour St. George's Sendall Tunnel
  • Taste Castara Bay Tobago's Creole
  • Stroll Admiralty Bay waterfront
  • View Saint Pierre colonial ruins
Starts / Ends
St. Georges / St. Georges
Activities
Local Market Visits
Activity Level
Variable
Embark on a 12-day cruise through the Southern Caribbean aboard the Star Clipper, starting in St. George’s, Grenada. Experience stunning beaches, vibrant local culture, and historical sites across Tobago, the Grenadines, Martinique, and Barbados.
Cruise Details
0
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Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
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TrustScore 4.9 of 5
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Based on 1057 reviews on
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1 week ago
Fabulous service for booking a cruise. Prompt response. Very satisfied
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review score
1 month ago
After booking a cruise directly with Explora.com, Mary Curry ace it simple to transfer our booking to Adventure Life, and we were surprised and delighted to receive onboard credits from switching to a third party agent.
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11 months ago
Mary is always a pleasure to work with. She is knowledgeable, prompt and gives good pros and cons for any choices we had to make.
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1 year ago
Jess is funtastic! She listens and fines the adventure I want to share with my granddaughter
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2 years ago
Angie was great! Always kept us informed of our trip. Great personality and easy to work with! Jean Hershey
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