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Top Caribbean Tours & Cruises in 2027

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Discover the best the world has to offer with Adventure Life’s expert-curated Caribbean tours 2027. From Gustavia, Bridgetown, Falmouth, Marigot, and Soufriere to hidden gems off the beaten path, our 18 top-rated itineraries take you deep into Caribbean’s breathtaking landscapes. Guided by bilingual experts, these immersive experiences cater to adventurers seeking unique journeys in small groups or customizable private tours.

Choose from a variety of 7 to 15 days itineraries starting at $2,010 to $84,290. You’ll find options that suit your travel style. Whether you’re passionate about Snorkeling, Village Visits, Archaeological Site Visits, Small Ship Sailing, and Wildlife Viewing or eager to explore Caribbean’s rich culture and natural beauty, our Caribbean tours 2027 deliver unforgettable moments. Each itinerary blends awe-inspiring exploration with a commitment to sustainability to ensure your adventure supports the preservation of our planet.

Adventure Life’s dedication to personalized travel promises your Caribbean tour 2027 is seamless from start to finish. From arranging transportation to selecting accommodations tailored to your preferences, we’ll take care of every detail. Our expert recommendations and insider tips make your journey even more enriching.

Contact our specialists today to start planning your Caribbean tour 2027. Whether you’re a solo traveler, a couple, or part of a group, Adventure Life will create a transformative experience you’ll treasure forever.
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    • Caribbean
Pink beach huts in the Caribbean
from $2,080
EXPLORE

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 sunny beaches of the Caribbean
from $9,990
2for1
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Soak in Soufriere’s volcanic spring
  • Explore Les Saintes’ French charm
  • Visit Antigua’s Nelson’s Dockyard
  • Stroll Nevis’ Georgian towns
Starts / Ends
Bridgetown / Marigot
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
Cruise Details
0
White Sand Beach in Barbados
from $2,080
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
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
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
0
Pig Beach in Exuma, Bahamas where wild pigs swim in the clear turquoise waters
from $19,990
2for1
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
2for1
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
0
Boats Moored to the Quay at Bridgetown Harbour
from $15,980
2for1
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, Village Visits, Archaeological Site Visits, 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
0
Explore colorful Bridgetown, Barbados
from $9,990
2for1
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
Visit beautiful Norman Island
from $9,990
2for1
EXPLORE

Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara
  • Explore Saint John's pristine beach
  • Stroll Philipsburg's lively markets
  • Snorkel Norman Island's caves
  • Visit 'The Baths' in Virgin Gorda
Starts / Ends
St. Thomas / St. Thomas
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty.
Cruise Details
0
Gustavia Harbor in St. Barths
from $9,990
2for1
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
0
Learn about the history of the Caribbean
from $9,990
2for1
EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Prickly Pear Cays waters
  • Admire Nevis’ Georgian buildings
  • Visit Soufriere’s volcanic springs
  • Wander Bridgetown’s streets
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.
Cruise Details
0
The Southeast Peninsula of Saint Kitts with Nevis in the Background
from $9,990
2for1
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
2for1
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
0
Caribbean landscapes and harbors
from $11,990
2for1
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
0
Explore the famous rock formations of the baths
from $9,190
2for1
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
Activities
Urban Exploration
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
Beautiful beach in Dominica
from $8,220
EXPLORE

Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
  • Enjoy iconic pitons of Saint Lucia
  • Learn about Kalinago culture
  • Explore Tobago Cays' coral reefs
  • Relax on Marie-Galante's beaches
Starts / Ends
Dominica / Anses d'Arlet
Activities
Scuba Diving
Activity Level
Variable
Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint Vincent and the Grenadines, snorkeling in Tobago Cays' clear waters. Experience sunsets, local culture, and beaches in Marie-Galante. This cruise combines relaxation and adventure in the Caribbean.
Cruise Details
0
Relax on the sunny beaches of the Bahamas
from $24,990
2for1
EXPLORE

Sounds of Discovery: New York to the Bahamas

New York - Nassau - 13 Day Itinerary aboard Scenic Eclipse
  • Explore Buenos Aires’ districts
  • Admire Ushuaia’s landscapes
  • Navigate Beagle Channel
  • Witness Antarctic wildlife
Starts / Ends
New York City / Nassau
Activities
Whale Watching
Activity Level
Variable
Experience a 13-day cruise from New York City to Nassau aboard the Scenic Eclipse, featuring stops in Bermuda, Turks and Caicos, San Salvador, Bimini, and Miami. This journey blends culture, history, and relaxation.
Cruise Details
0
Balboa
from $3,150
EXPLORE

Panama to Aruba

12 Day Itinerary aboard Star Clipper
  • Transit the Panama Canal locks
  • Walk colonial Balboa streets
  • Explore forts in Portobelo
  • Visit San Blas and Guna villages
  • See Cartagena and Santa Marta
Starts / Ends
Balboa / Oranjestad
Activities
Small Ship Sailing
Activity Level
Variable
Sail the Panama Canal on a 10-day Star Clippers cruise through Central America. Begin in Balboa, then transit the Panama Canal and see the locks in action. Explore Spanish forts in Portobelo, meet the Guna people in the San Blas Islands, and discover Colombia’s coastal cities of Cartagena and Santa Marta. Enjoy scenic days under sail.
Cruise Details
0
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