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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, Marigot, Falmouth, Soufriere, and Iles des Saintes to hidden gems off the beaten path, our 7 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 $7,190 to $61,780. You’ll find options that suit your travel style. Whether you’re passionate about cruises, snorkeling, archaeological site visits, beaches, and wildlife viewing or eager to explore Caribbean’s rich culture and natural beauty, our 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
$7,590
2-for-1
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Bridgetown's culture
  • Stroll Gustavia's colorful streets
  • Admire Marigot’s scenic coastline
  • Savor Soufriere's delicious cuisine
Starts / Ends:
Bridgetown / Marigot
Activities:
Small Ship Sailing
Activity Level:
Variable
Embark on this 8-day Caribbean cruise aboard the Emerald Azzurra, beginning in Barbados. Relax with a rejuvenating mud bath or soak in the therapeutic hot springs of Soufriere. Explore the UNESCO-listed Nelson’s Dockyard in Falmouth Harbor and unwind on the serene beaches of Iles des Saintes. …
Cruise Details
0
Experience laid-back Marigot
$15,980
2-for-1
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
Activities:
Small Ship Cruises, Snorkeling, Village Visits
Activity Level:
Variable
Embark on a 15-day cruise from Marigot aboard an Emerald Azzurra. Discover the serene beauty of Anguilla, which is celebrated for its pristine white-sand beaches and vibrant coral reefs. Explore the historic charm of UNESCO-listed Nelson’s Dockyard in Falmouth Harbor and uncover the tranquil …
Cruise Details
0
Visit beautiful Norman Island
$7,590
2-for-1
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
Activities:
Archaeological Site Visits, Local Market Visits, Snorkeling
Activity Level:
Variable
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Saint Thomas. Discover Virgin Gorda, home to The Baths, a mesmerizing collection of natural pools and grottoes formed by massive granite boulders. Sail to Norman Island, renowned for its crystal-clear waters and vibrant …
Cruise Details
0
Explore the famous rock formations of the baths
$7,990
2-for-1
EXPLORE

Quintessential Caribbean

8 Day Itinerary aboard Emerald Sakara
  • Relax on Prickly Pear Cays' beaches
  • Visit Guadeloupe’s fishing village
  • Visit port of Falmouth Harbour
  • Wander through lively Cruz Bay
Starts / Ends:
San Juan / St. Thomas
Activities:
Archaeological Site Visits, Local Market Visits, Urban Exploration
Activity Level:
Variable
Set sail on an 8-day Caribbean adventure aboard the Emerald Sakara. Discover the vibrant culture and historic charm of San Juan, Puerto Rico, and the lively atmosphere of Saint John in the US Virgin Islands. Enjoy the serene beaches and historic sites of Nevis, and immerse yourself in the …
Cruise Details
0
Gustavia Harbor in St. Barths
$7,590
2-for-1
EXPLORE

Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Azzurra
  • Dive in Anguilla
  • Explore Virgin Gorda
  • Discover Anegada
  • Experience Jost van Dyke
Starts / Ends:
Marigot / Marigot
Activities:
Small Ship Cruises, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Embark on an 8-day Caribbean cruise aboard Emerald Azzurra. Start in Marigot, Saint Martin, and board your luxury yacht. Cruise to Anguilla, known for its coral beaches and clear waters, and snorkel over vivid coral reefs. Visit Virgin Gorda to see the Baths, impressive granite grottoes formed by …
Cruise Details
0
Gustavia Harbor in St. Barths
$7,590
2-for-1
EXPLORE

Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Bridgetown's culture
  • Stroll Gustavia's colorful streets
  • Admire Marigot’s scenic coastline
  • Savor Soufriere's delicious cuisine
Starts / Ends:
Marigot / Bridgetown
Activities:
Small Ship Sailing, Village Visits, Wildlife Viewing
Activity Level:
Variable
Embark on an 8-day cruise departing from Marigot aboard the Emerald Azzura. This journey includes visiting Anguilla, which is celebrated for its unspoiled white-sand beaches and vibrant coral reefs. Next, explore Gustavia, known for its charming, colorful houses and distinctive architecture. The …
Cruise Details
0
Panorama of Les Saintes
$7,190
2-for-1
EXPLORE

Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra
  • Visit UNESCO-listed Nelson's dock
  • Discover quaint island towns
  • Stroll Gustavia’s colorful street
  • Dip into a therapeutic mud bath
Starts / Ends:
Bridgetown / Marigot
Activities:
Archaeological Site Visits
Activity Level:
Variable
Set sail on a 7-day Caribbean cruise aboard the luxurious Emerald Azzurra. Begin in Barbados, soaking in vibrant culture and stunning beaches. In Soufrière, indulge in volcanic mud baths and explore scenic volcanic landscapes. At Falmouth Harbour, visit Nelson’s Dockyard, a UNESCO …
Cruise Details
0
1-7 of 7 Results
TrustScore 4.8 | 417 reviews
TrustScore 4.8 of 5
total score
Based on 417 reviews on
review score
4 hours ago
Adventure Life has been great throughout my planning process for our up and coming Galapagos cruise. Kevin Moore, in particular, was very helpful in assisting me in making choices and providing me with options. He was also very patient, as I worked through figuring out what I really wanted in this vacation.
Lucy Greenway
review score
4 hours ago
Adventure Life was a pleasure to work with. They helped us find different options for our charter and answered a lot of questions with patience and clarity.
Brooke Hopper
review score
1 day ago
Excellent service, great hotels and well organized excursions with expert guides! Highly recommended!
Shadi Dalili
review score
2 days ago
Clara Tort has been our Travel Advisor for Buenos Aires, then for Iguazu, then for Mendoza and Aconcagua Trekking, and then for Patagonia and Fitz Roy trekking. She has navigated with us through our travels, and now we are coming back for more- onto Machu Pichu and Peru.
Gus ORDONEZ
review score
2 days ago
Mary Curry made the experience wonderful for the second time. She is the reason we returned to Adventure Life to book our second cruise on WindStar. She is tireless, well informed, pleasant to work with and totally reliable. If you offer employees bonuses, give her one! there who answered to phone to help us book shore excursions were also very good and easy to work with - and we demand rather an lot of help.
Laura Flanagan

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