Select one of the below 3 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 $2,010 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 $2,010

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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!

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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.

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Relax on the white sandy beaches of the Caribbean

from $2,010

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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
Activities: Small Ship Sailing, Snorkeling
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.

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