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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 Iles des Saintes to hidden gems off the beaten path, our 10 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 $3,150 to $84,290. You’ll find options that suit your travel style. Whether you’re passionate about Small Ship Sailing, Snorkeling, Archaeological Site Visits, Village Visits, and Local Market Visits 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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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
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
Wildlife Viewing, Helicopter Tours, Kayaking, Village Visits, Stand Up Paddle Boarding
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
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
Explore the famous rock formations of the baths
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
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
Snorkeling, Small Ship Sailing, Archaeological Site Visits, Local Market Visits
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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