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Virgin Islands Small Ship Sailing

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Relax on the beaches of St. Maarten
from $2,010
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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
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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
0
Learn about the history of the Caribbean
from $6,995
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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
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Soufriere bay, St Lucia
from $6,495
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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
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
0
St Barts harbor view
from $2,010
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Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Explore Nevis sugar plantations
  • Tour Dominica rainforests
  • Snorkel Terre-de-Haut waters
  • Visit famous Nelson's Dockyard
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Embark on an 8-day roundtrip cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring St. Maarten, Nevis, Dominica, Antigua, and St. Barts. Experience stunning beaches, vibrant culture, and unique natural landscapes across the Leeward Islands.
Cruise Details
0
Beach, harbor and village of Terre-de-Haut
from $2,010
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Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Swim Gustavia beaches
  • Visit Nelson's Dockyard ruins
  • Snorkel Terre-de-Haut waters
  • Hike Dominica trails
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Embark on an 8-day Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring charming towns, lush rainforests, and beautiful beaches. Enjoy duty-free shopping in Gustavia before returning to St. Maarten.
Cruise Details
0
Visit beautiful Basseterre
from $2,650
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Leeward Islands Christmas Cruise

Philipsburg Roundtrip - 10 Day Itinerary aboard Star Flyer
  • Celebrate Christmas in Anguilla
  • Sail beside Royal Clipper
  • Explore the Iles des Saintes
  • Relax on South Friars Bay beach
Starts / Ends
Philipsburg / Philipsburg
Activities
Snorkeling, Small Ship Sailing, Stand Up Paddle Boarding, Kayaking, Scuba Diving
Activity Level
Variable
Spend Christmas on this 10-day Caribbean cruise aboard Star Flyer, roundtrip from St. Maarten to Nevis, Dominica, Guadeloupe, the Iles des Saintes, Antigua, St. Barts, Anguilla, and St. Kitts. A good fit for travelers who want a relaxed holiday cruise, with small harbors in place of big-ship crowds.
Cruise Details
0
White Sand Beach in Barbados
from $2,080
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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
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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
Activities
Wildlife Viewing, Local Market Visits
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
Stroll along the beautiful beaches of the Caribbean
from $3,860
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Grenadine Islands Christmas Cruise

Roundtrip Bridgetown - 11 Day Itinerary aboard Royal Clipper
  • Relax on beaches in Martinique
  • Snorkel reefs in Terre de Haut
  • Swim in South Friar's Bay
  • Explore the Tobago Cays
Starts / Ends
Bridgetown / Bridgetown
Activities
Village Visits, Archaeological Site Visits, Hiking
Activity Level
Variable
Set sail on an 11-day New Year's Caribbean cruise aboard the Royal Clipper, visiting beautiful spots like Grenada, St. Lucia, and Dominica. Enjoy snorkeling in Tobago Cays, relaxing at Diamond Falls, and exploring historic sites in Antigua and St. Kitts before concluding your adventure in Bridgetown.
Cruise Details
0
View of Mount Pelée overlooking Saint-Pierre, northwest Martinique, French Caribbean island
from $6,995
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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
Magnificent sailing ship moored in the Soufrière Bay, on the southwest coast of Saint Lucia.
from $2,010
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Grenada to Antigua

St George - St John - 8 Day Itinerary aboard Star Clipper
  • Tour St. George's Fort George
  • Visit Bequia Port Elizabeth
  • Snorkel Tobago Cays
  • Relax on Martinique turquoise water
Starts / Ends
St. Georges / St. John's
Activity Level
Variable
Embark on an 8-day cruise from St. George’s, Grenada, aboard the Star Clipper, visiting highlights like Fort George and the Tobago Cays for snorkeling. The journey wraps up in St. Kitts after exploring St. Lucia's Pitons, Martinique's beaches, and Dominica's rainforests.
Cruise Details
0
13-24 of 29 Results

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Hike through meadows and ruins on St. Johns
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TrustScore 4.9 | 1083 reviews
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Fabulous service for booking a cruise. Prompt response. Very satisfied
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2 months 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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1 year 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.
MTPhil
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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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