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Sailing Trips in Norman Island

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Choose from one of these 9 Norman Island sailing cruises in 2026. Sailing with the sails full and the sun shining is an unforgettable experience that Adventure Life's Norman Island sailing cruise experts can help you plan to perfection. Contact one of our Norman Island sailing cruise experts for help planning your next trip.
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    • Norman Island
Tropical waterfall and turquoise pool in lush forest of Dominica
from $2,010
Air Credit
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
Panoramic view from Shirley Heights, Antigua, showing English Harbor and Caribbean landscape
from $6,995
EXPLORE

Pirate Islands With A Yachtie Vibe

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Gustavia harbor
  • Visit Shirley Heights, Antigua
  • Explore The Baths, Virgin Gorda
  • Sail Sir Francis Drake Channel
  • Experience Virgin Islands fun
Starts / Ends
Philipsburg / Philipsburg
Activities
Small Ship Sailing
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit on a Caribbean round-trip from Philipsburg, St. Maarten. Explore Gustavia, St. John’s, Virgin Gorda, Jost van Dyke, and Norman Island with beaches, sailing, and historic sights.
Cruise Details
0
Relax on the white sandy beaches of the Caribbean
from $2,010
Air Credit
EXPLORE

Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Visit Gustavia French boutiques
  • Hike Jost Van Dyke scenic trails
  • Tour Tortola to see Soper's Hole
  • Explore Basseterre landmarks
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.
Cruise Details
0
Visit beautiful Norman Island
from $2,010
EXPLORE

Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Visit Anguilla's white sand coves
  • Tour Tortola to see Soper's Hole
  • Swim South Friars Bay waters
  • Hike Jost Van Dyke trails
Starts / Ends
Philipsburg / Philipsburg
Activities
Snorkeling
Activity Level
Variable
Embark on an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, visiting beautiful locations like Anguilla, Tortola, and Virgin Gorda. Enjoy duty-free shopping in St. Barts and explore the colonial history of St. Kitts before returning to St. Maarten.
Cruise Details
0
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
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
Relax on the beaches of St. Maarten
from $2,010
EXPLORE

Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper
  • Hike St. Kitts rainforests
  • Tour Basseterre colonial history
  • Shop Philipsburg Dutch bargains
  • Explore Tortola to see Soper's Hole
Starts / Ends
St. John's / St. John's
Activity Level
Variable
Experience an 8-day round-trip cruise from St. John's, Antigua, aboard the Star Clipper, visiting destinations like St. Barts, the British Virgin Islands, and St. Maarten. Enjoy duty-free shopping, stunning beaches, and historic sites before concluding your journey in Antigua.
Cruise Details
0
Umbrellas and sunbeds lined up along the White Bay Beach of Jost Van Dyke, British Virgin Islands
from $2,010
EXPLORE

Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Visit Anguilla's white sand coves
  • Tour Tortola to see Soper's Hole
  • Swim South Friars Bay waters
  • Hike Jost Van Dyke trails
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Visit Anguilla's beaches, explore the British Virgin Islands, hike Jost Van Dyke, and enjoy shopping in St. Barts while uncovering historical sites and natural beauty.
Cruise Details
0
Sunset over Philipsburg
from $2,010
EXPLORE

Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Visit Anguilla's white sand coves
  • Tour Tortola to see Soper's Hole
  • Swim South Friars Bay waters
  • Hike Jost Van Dyke trails
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts.
Cruise Details
0
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