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Top St. Barth Trips & Tours

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Select one of the below 7 best St. Barth trips for 2026 and 2027. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Gustavia. Our St. Barth trips for 2026 feature Small Ship Sailing, and Snorkeling, and start from $1,970 for trips of 8 days. Contact Adventure Life's St. Barth trip planning experts to start planning your next seamless trip.
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Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,970
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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!
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St Barts harbor view
from $2,010
Air Credit
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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.
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Tropical Caribbean Beach in Martinique
from $2,010
Air Credit
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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.
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Explore beautiful Jost van Dyke
from $2,010
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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.
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Relax on the beaches of St. Maarten
from $2,010
Air Credit
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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.
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Sunset over Philipsburg
from $2,010
Air Credit
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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.
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Beach, harbor and village of Terre-de-Haut
from $2,010
Air Credit
EXPLORE

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
Activities
Small Ship Sailing, Snorkeling
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
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