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Explore the Caribbean

Virgin Islands Small Ship Sailing

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Discover the enchanting allure of the Virgin Islands with Adventure Life's array of 11 captivating small ship sailing experiences in 2025. Join us on a sailing adventure to explore the mesmerizing beauty and vibrant cultures of the Caribbean islands. From the turquoise waters of Antigua to the lush landscapes of St. Lucia, each moment offers a unique opportunity to immerse yourself in the wonders of the region. Experience the relaxed pace of small ship sailing as you swim and snorkel amidst the pristine waters, enjoy the French flair of Îles des Saintes, and witness breathtaking sunsets over the horizon. Engage in a variety of activities like snorkeling, wildlife viewing, and discovering hidden beaches, all while surrounded by the natural splendor of the Caribbean. Don't miss this chance to sail away from the ordinary and embark on a journey of a lifetime. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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Explore the famous rock formations of the baths
from $6,995
No SS
EXPLORE

Across a sea of idyllic Islands

Philipsburg, St. Maarten Round - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore chic St. Barths
  • Relax at Great Bay
  • Visit Virgin Gorda
  • Cruise Sir Francis Channel
Starts / Ends
Philipsburg / Philipsburg
Activities
Small Ship Sailing, Snorkeling, Stand Up Paddle Boarding
Activity Level
Variable
Set sail on an unforgettable 8-day Caribbean cruise aboard the Sea Cloud Spirit. Experience the charm of St. Maarten, Antigua, St. Barths, and the Virgin Islands as you explore paradise by sea. Discover rich culture, pristine beaches, and lively island towns filled with color and charm.
Cruise Details
0
Pink beach huts in the Caribbean
from $2,030
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
0
Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,970
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
0
Gustavia Harbor in St. Barths
from $1,970
EXPLORE

Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper
  • Explore St. John's dockyards
  • Sail Sir Francis Drake Channel
  • Stroll Norman Island's beach
  • Tour Basseterre's old plantations
Starts / Ends
St. John's / St. John's
Activities
Village Visits, Local Market Visits
Activity Level
Variable
Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.
Cruise Details
0
The crystal blue water of Jost van Dyke
from $3,090
EXPLORE

Jamaica to Antigua

12 Day Itinerary aboard Star Clipper
  • Swim in Montego Bay's waters
  • Explore Santo Domingo
  • Visit the Treasure Island
  • Hike Virgin Gorda trails
Starts / Ends
Port Antonio / St. John's
Activities
Spa Relaxation
Activity Level
Variable
Explore a paradise of vibrant coral reefs, powder-soft sand, and warm island hospitality on this 12-day cruise from Jamaica to Antigua aboard Star Clipper. Experience crystal-clear water, bright skies, and gentle breezes. Relish in the beauty of untouched beaches and become enchanted by seductive scents and rhythms.
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
Activities
Wildlife Viewing
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 $1,970
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
Activity Level
Variable
The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.
Cruise Details
0
Georgian Architecture, St. George's | Grenada
from $2,820
EXPLORE

Grenada to Antigua

St. George - St. John - 11 Day Itinerary aboard Star Clipper
  • Explore St. George’s harbor
  • Experience Charlotteville coast
  • Relax at Englishman’s Bay
  • Wander through Admiralty Bay
Starts / Ends
St. Georges / St. John's
Activity Level
Variable
Take an 11-day cruise on the Star Clipper from St. George's, Grenada to St. John's, Antigua, exploring secluded bays and historic towns in Tobago and the Grenadines. Enjoy highlights like snorkeling in Tobago Cays and relaxing on beautiful beaches, while immersing yourself in vibrant local cultures.
Cruise Details
0
Beautiful beach in Dominica
from $8,220
EXPLORE

Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
  • Enjoy iconic pitons of Saint Lucia
  • Learn about Kalinago culture
  • Explore Tobago Cays' coral reefs
  • Relax on Marie-Galante's beaches
Starts / Ends
Dominica / Anses d'Arlet
Activities
Scuba Diving
Activity Level
Variable
Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint Vincent and the Grenadines, snorkeling in Tobago Cays' clear waters. Experience sunsets, local culture, and beaches in Marie-Galante. This cruise combines relaxation and adventure in the Caribbean.
Cruise Details
0
Panama's turquoise waters
from $4,450
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Explore Balboa’s colonial charm
  • Transit Panama’s iconic canal
  • Discover San Blas culture
  • Enjoy Aruba’s clear waters
Starts / Ends
Balboa / St. John's
Activities
Archaeological Site Visits
Activity Level
Variable
Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.
Cruise Details
0
White Sand Beach in Barbados
from $2,030
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
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