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Top Caribbean Trips & Tours

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Sunset over Philipsburg
from $2,010
SS 25%
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
Beach, harbor and village of Terre-de-Haut
from $2,010
SS 25%
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
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
0
View of Mount Pelée overlooking Saint-Pierre, northwest Martinique, French Caribbean island
from $6,995
EBD 30%
EXPLORE

Sun-Drenched Sailing Days

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Philipsburg beaches
  • Visit Saint-Pierre ruins
  • Uncover St. Lucia’s Pitons
  • Discover Dominica’s jungle
Starts / Ends
Philipsburg / Philipsburg
Activities
Rainforest Exploration
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit through the Caribbean, Lesser Antilles & Grenadines. You explore St. Maarten, Martinique, St. Lucia, Dominica, Nevis, and Anguilla, combining colonial towns, volcanic peaks, rainforests, and white-sand beaches with authentic sailing experiences at sea.
Cruise Details
0
Visit Las Palmas’ Santa Ana Cathedral, a central landmark in the city
from $13,695
EBD 30%
EXPLORE

Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Philipsburg - 17 Day Itinerary aboard Sea Cloud Spirit
  • Experience Transatlantic Crossing
  • See the Gran Canaria landscapes
  • Explore Las Palmas old town
  • Climb rigging and set sails
Starts / Ends
Las Palmas / Philipsburg
Activity Level
Variable
Experience 17 days aboard Sea Cloud Spirit on a transatlantic crossing from Las Palmas to Philipsburg. Relax on deck, enjoy wellness programs, and explore Gran Canaria’s landscapes before arriving in the Caribbean.
Cruise Details
0
Take a leisurely stroll through beautiful Bridgetown
from $13,655
EBD 30%
EXPLORE

Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Bridgetown - 18 Day Itinerary aboard Sea Cloud II
  • Experience Transatlantic Crossing
  • Sail under full sails
  • Visit Santa Ana Cathedral
  • Explore Bridgetown, Barbados
Starts / Ends
Las Palmas / Bridgetown
Activities
Small Ship Sailing, Village Visits
Activity Level
Variable
Take part in an 18-day transatlantic cruise aboard Sea Cloud II from Las Palmas, Gran Canaria to Bridgetown, Barbados. Relax under full sails, explore Gran Canaria’s landscapes, and discover Bridgetown’s UNESCO World Heritage colonial architecture and beaches.
Cruise Details
0
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