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

Sailboat Cruises in Lesser Antilles

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    • Lesser Antilles
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
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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
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
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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
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
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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
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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
Village Visits, 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
Visit beautiful Basseterre
from $2,620
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Windward Islands

Roundtrip Bridgetown - 8 Day Itinerary aboard Royal Clipper
  • Stroll through historic Bridgetown
  • Enjoy sunny Rodney Bay
  • Swim in South Friar's Bay
  • Tour historic St. Kitts
Starts / Ends
Bridgetown / Bridgetown
Activities
Archaeological Site Visits, Hiking
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Royal Clipper, visiting Saint Lucia, Dominica, and Antigua, among other beautiful islands. Enjoy activities like hiking, snorkeling, and water sports before concluding your journey in Bridgetown.
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
Tropical Caribbean Beach in Martinique
from $2,010
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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper
  • Explore St. John's dockyards
  • Tour Basseterre colonial history
  • Hike St. Kitts rainforests
  • Swim South Friars Bay waters
Starts / Ends
St. John's / St. John's
Activity Level
Variable
Join an 8-day Caribbean cruise from St. John's, Antigua, on the Star Clipper, exploring destinations like St. Barts, St. Kitts, and Martinique. Experience snorkeling, historic tours, and diverse beaches while enjoying the beauty of the French and British West Indies.
Cruise Details
0
The crystal blue water of Jost van Dyke
from $2,020
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Antigua to Antigua

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper
  • Explore Antigua harbor docks
  • Swim Virgin Gorda baths
  • Enjoy Anguilla beach resorts
  • Tour St Kitts plantations
Starts / Ends
St. John's / St. John's
Activity Level
Variable
8-day itinerary from St John's Antigua aboard Star Clipper calling at St Barts, BVI islands including Norman Island, Virgin Gorda, Jost van Dyke, Anguilla and St Kitts. Route includes historic harbors, small towns, beaches and sailing passages across the Caribbean.
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
Magnificent sailing ship moored in the Soufrière Bay, on the southwest coast of Saint Lucia.
from $2,010
EXPLORE

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
Explore beautiful Jost van Dyke
from $2,010
EXPLORE

Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper
  • Explore St. John's dockyards
  • Sail Sir Francis Drake Channel
  • Swim Virgin Gorda Baths
  • Hike Jost van Dyke trails
Starts / Ends
St. John's / St. John's
Activity Level
Variable
Set sail on an 8-day round-trip cruise from St. John’s, Antigua, aboard the Star Clipper, exploring St. Barts, the British Virgin Islands, and Anguilla. Highlights include duty-free shopping, scenic hikes, and beautiful beaches before concluding in Antigua.
Cruise Details
0
13-24 of 40 Results

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Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
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Angie was great! Always kept us informed of our trip. Great personality and easy to work with! Jean Hershey
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