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Road Bay

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Anguilla
Snorkeling in the Caribbean with a starfish
Antigua
Lush green forests and clear blue waters of the Caribbean
Aruba
Relax on the shores of the Caribbean
Barbados
Take a leisurely stroll through beautiful Bridgetown
British Virgin Islands
Relax on the beaches of the Caribbean
Grenada
Snorkel the clear, tropical waters
Greater Antilles
Picturesque Cuba
Lesser Antilles
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
Dominica
Encounter tropical wildlife while you sail on the Aranui
Netherlands Antilles
Enjoy a blissful snorkeling trip.
Puerto Rico
Discover incredible history and culture in Puerto Rico
St. Barth
Play on the famously beautiful beaches of St. Barth's
St. Kitts
Stroll along the beautiful beaches of the Caribbean
St. Martin
Pelicans hanging out in the ocean
St. Vincent des Grenadines
Visit beautiful St. Vincent
Union Island
Uwe Moser
Bright blue waters of the Caribbean
British Virgin Islands
Relax on the beaches of the Caribbean
Virgin Islands
Relax on the beaches of the Caribbean
U.S. Virigin Islands
View gorgeous sunsets over the Virgin Islands
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Select one of the below 5 best Road Bay trips for 2026 and 2027. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring . Our Road Bay trips for 2026 feature Small Ship Sailing, and Snorkeling, and start from $2,010 for trips of 8 days. Contact Adventure Life's Road Bay trip planning experts to start planning your next seamless trip.
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    • Road Bay
Relax on the white sandy beaches of the Caribbean
from $2,210
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
Explore beautiful Jost van Dyke
from $2,010
Air Credit
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
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
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
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
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, Small Ship Sailing
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
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