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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
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
Boats Moored to the Quay at Bridgetown Harbour
from $15,980
Up to 40%
EXPLORE

Discover the Pearls of the Caribbean

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Soufriere’s volcanic peaks
  • Tour Falmouth’s colonial forts
  • Snorkel Anguilla’s coral reefs
  • Wander Marigot’s French markets
Starts / Ends
Marigot / Bridgetown
Activities
Village Visits, Wildlife Viewing, Local Market Visits, Archaeological Site Visits
Activity Level
Variable
Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.
Cruise Details
0
Explore the famous rock formations of the baths
from $21,780
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Discover the Pearls of the Caribbean

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Soufriere’s volcanic peaks
  • Tour Falmouth’s colonial forts
  • Snorkel Anguilla’s coral reefs
  • Wander Marigot’s French markets
Starts / Ends
Bridgetown / Marigot
Activities
Kayaking
Activity Level
Variable
Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.
Cruise Details
0
Pink beach huts in the Caribbean
from $2,080
SS 25%
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Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.
Cruise Details
0
Relax on the beaches of St. Maarten
from $2,010
Air Credit
EXPLORE

Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer
  • Explore Nevis sugar plantations
  • Visit Dominica boiling lakes
  • Snorkel Terre-de-Haut blue waters
  • Swim South Friars Bay clear waters
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.
Cruise Details
0
Learn about the history of the Caribbean
from $6,995
EXPLORE

Across A Sea Of Idyllic Islands

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore St. Maarten’s cultures
  • Visit Virgin Gorda’s Baths
  • Discover Jost van Dyke
  • Wander Gustavia, St. Barths
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Sail 8 days aboard Sea Cloud Spirit through the Caribbean’s Lesser Antilles & Grenadines. Discover St. Maarten, Virgin Gorda, Jost van Dyke, Norman Island, St John’s, and St. Barths while enjoying authentic tall-ship sailing and idyllic island scenery.
Cruise Details
0
Soufriere bay, St Lucia
from $6,495
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Relax The Caribbean Way

Roundtrip Bridgetown - 8 Day Itinerary aboard Sea Cloud II
  • Snorkel in the Tobago Cays
  • Discover Grenada’s spices
  • Explore Saint-Pierre, Martinique
  • View Gros and Petit Piton
Starts / Ends
Bridgetown / Bridgetown
Activities
Snorkeling, Small Ship Sailing, Stand Up Paddle Boarding
Activity Level
Variable
Experience an 8-day voyage aboard Sea Cloud II roundtrip from Bridgetown, Barbados, through the Lesser Antilles & Grenadines. You snorkel in the Tobago Cays, explore spice-rich Grenada, visit Saint-Pierre in Martinique, admire St. Lucia’s Pitons, and enjoy Caribbean sunsets at sea.
Cruise Details
0
St Barts harbor view
from $2,010
Air Credit
EXPLORE

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.
Cruise Details
0
Beach, harbor and village of Terre-de-Haut
from $2,010
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
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
Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
Up to 40%
EXPLORE

Island Odyssey: Bahamas to the Grenadine

Nassau - Bridgetown - 11 Day Itinerary aboard Scenic Eclipse
  • Explore Nassau’s vibrant capital
  • Visit Staniel Cay’s beaches
  • Discover San Salvador’s coral reefs
  • Stroll St. Barts iconic Shell Beach
Starts / Ends
Nassau / Bridgetown
Activities
Helicopter Tours
Activity Level
Variable
Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.
Cruise Details
0
White Sand Beach in Barbados
from $2,080
SS 25%
EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.
Cruise Details
0
Dock going out into the crystal blue ocean
from $2,080
EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Explore Antigua’s vibrant dockyards
  • Discover Les Saintes’ beaches
  • Relax on Martinique’s white sands
  • Stroll Grenada’s aromatic markets
Starts / Ends
St. John's / Bridgetown
Activity Level
Variable
Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.
Cruise Details
0
13-24 of 28 Results

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Hike through meadows and ruins on St. Johns
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