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All Anguilla Small Ship Cruise & Tour Deals

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Select one of the below 3 best Anguilla trips for 2026 and 2027. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Road Bay. Our Anguilla trips for 2026 feature Small Ship Sailing, and Snorkeling, and start from $1,970 for trips of 8 days. Contact Adventure Life's Anguilla trip planning experts to start planning your next seamless trip.
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    • Anguilla
Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,970
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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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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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Sunset over Philipsburg
from $2,010
Air Credit
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
Small Ship Sailing, Snorkeling
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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