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Top Caribbean Tours & Cruises in 2027

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Tropical waterfall and turquoise pool in lush forest of Dominica
from $2,010
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
Activities
Small Ship Sailing
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!
Cruise Details
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Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
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
Stand Up Paddle Boarding, Kayaking, 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
Experience laid-back Marigot
from $15,980
EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Anguilla, serene landscapes
  • Savor Barbados’s cultural delights
  • Visit Antigua’s historic dockyard
  • Stroll Nevis’s serene beaches
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.
Cruise Details
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Boats Moored to the Quay at Bridgetown Harbour
from $15,980
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
Snorkeling, Local Market Visits, Wildlife Viewing
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
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City of Basseterre and Frigate Bay from the Timothy Hill viewpoint in St. Kitts.
from $12,690
EXPLORE

Discover the Pearls of the Caribbean

Bridgetown - Sint Maarten - 15 Day Itinerary aboard Emerald Sakara
  • Visit Soufriere mud baths
  • Tour Iles des Saintes Fort Napoleon
  • See St. John's Nelson’s Dockyard
  • Observe Anguilla beaches
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Set sail on a 15-day Caribbean cruise from Barbados aboard the Emerald Sakara, visiting Saint Lucia for its mud baths, Antigua's historic dockyard, and Anguilla's vibrant coral reefs. Conclude your journey in Philipsburg, Sint Maarten, enjoying the region's rich culture and cuisine.
Cruise Details
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Enjoy the beautiful blue Caribbean
from $12,690
EXPLORE

Discover the Pearls of the Caribbean

Sint Maarten - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Experience Soufriere mud baths
  • See St. John's Nelson’s Dockyard
  • Discover Charlestown beaches
  • Visit Gustavia painted houses
Starts / Ends
Philipsburg / Bridgetown
Activities
Archaeological Site Visits, Village Visits
Activity Level
Variable
Set sail on a 15-day Caribbean cruise aboard the Emerald Sakara, visiting islands like Anguilla for snorkeling and Virgin Gorda for stunning rock formations. Explore vibrant Gustavia in Saint Barthelemy, enjoy the charm of the Iles des Saintes, relax in Saint Lucia's hot springs, and experience the colonial beauty of Barbados.
Cruise Details
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Explore colorful Bridgetown, Barbados
from $9,990
EXPLORE

Grenadines & Windwards Yachting

Bridgetown, Barbados Roundtrip - 8 Day Itinerary aboard Emerald Azzurra
  • Explore historic Kingstown
  • Swim Tobago Cays reefs
  • Discover Mayreau views
  • Relax on Bequia Island
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Embark on an 8-day Caribbean cruise from Bridgetown, Barbados aboard Emerald Azzurra. Visit Kingstown, Bequia, Mayreau, Union Island, and Tobago Cays. Discover small island communities, historical landmarks, coral reefs, and quiet beaches. Enjoy daily opportunities for swimming, snorkeling, and local exploration in Saint Vincent and the Grenadines.
Cruise Details
0
Gustavia Harbor in St. Barths
from $9,990
EXPLORE

Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Anguilla’s coral coastlines
  • Visit Virgin Gorda granite boulders
  • Discover Norman Island's coves
  • Relax on Anegada’s remote sands
Starts / Ends
Marigot / Marigot
Activities
Hiking
Activity Level
Variable
Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
Cruise Details
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The Southeast Peninsula of Saint Kitts with Nevis in the Background
from $9,990
EXPLORE

Quintessential Caribbean

St Thomas - San Juan - 8 Day Itinerary aboard Emerald Sakara
  • Explore Cruz Bay town
  • Visit Nevis plantations
  • Discover Nelson’s Dockyard
  • Swim Prickly Pear Cays
Starts / Ends
St. Thomas / San Juan
Activity Level
Variable
Explore the Caribbean on an 8-day cruise from Saint Thomas to San Juan aboard Emerald Sakara. Visit Saint John, Nevis, Guadeloupe, Antigua, Saint Barthélemy, and the British Virgin Islands. Discover UNESCO-listed landmarks, swim in clear waters, and experience regional architecture, food, and history throughout the journey.
Cruise Details
0
Islands of the Caribbean
from $7,990
EXPLORE

Quintessential Caribbean

San Juan - St Thomas - 8 Day Itinerary aboard Emerald Sakara
  • Relax on Prickly Pear Cays' beaches
  • Visit Guadeloupe’s fishing village
  • Visit port of Falmouth Harbor
  • Wander through lively Cruz Bay
Starts / Ends
San Juan / St. Thomas
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays.
Cruise Details
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Caribbean landscapes and harbors
from $11,990
EXPLORE

Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra
  • Visit UNESCO-listed Nelson's dock
  • Discover Iles des Saintes town
  • Stroll Gustavia’s colorful street
  • Dip into a therapeutic mud bath
Starts / Ends
Bridgetown / Marigot
Activity Level
Variable
Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
Cruise Details
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Explore the famous rock formations of the baths
from $9,190
EXPLORE

Splendours of the Caribbean

San Juan - St. Thomas - 7 Day Itinerary aboard Emerald Sakara
  • Tour Nelson’s Dockyard
  • Explore Nevis Island plantations
  • Walk through Gustavia
  • Swim Prickly Pear Cays
Starts / Ends
San Juan / St. Thomas
Activity Level
Variable
Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.
Cruise Details
0
13-24 of 56 Results

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Franny F.
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