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Greater Antilles Tours & Cruises in 2026

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Experience the stunning beauty and rich culture of the Greater Antilles on our 5 diverse tours & cruises for 2026. Explore the vibrant destinations of the Caribbean, from the lush landscapes of Cuba to the historical sites of the Dominican Republic and the picturesque beaches of Puerto Rico. Immerse yourself in the local flavors and rhythms of the region, with opportunities for cultural experiences, wildlife viewing, and beach relaxation over 5 to 12 days. Discover the colorful streets of Havana, taste the flavorsome cuisine of the islands, and soak up the warm hospitality of the Caribbean people. With tours starting at $2,245 to $30,490, there's no better time to embark on a journey that will leave you with unforgettable memories of the Greater Antilles. To start planning your dream Caribbean adventure, contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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Kayaking in Cuba
$2,245
EXPLORE

Cuba Kayaking West Tour

8 Day Itinerary
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Activities:
Homestays, Kayaking, Snorkeling
Activity Level:
Easy Active
The world’s fascination with Cuba has lasted for many generations, and for good reason. Cuba is a cultural hub, with a mix of descendants of indigenous people, European immigrants, and slaves. The country's music and art draw from these diverse influences. Cuba has also exerted an …
Tour Details
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Nassau Lighthouse
$7,590
EXPLORE

Caribbean Escapade

8 Day Itinerary aboard Emerald Sakara
  • Explore the pristine beaches
  • Snorkel in crystal-clear waters
  • Relax on secluded Gordon’s Beach
  • Explore Grand Turk’s beaches
Starts / Ends:
San Juan / Miami
Activities:
Kayaking, Snorkeling
Activity Level:
Variable
Experience an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's sandy shores and historical attractions, discover Long Island’s serene Gordon's Beach, and dive into San Salvador’s vibrant coral reefs and historical sites. Enjoy the breathtaking beauty of …
Cruise Details
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The crystal blue water of Jost van Dyke
$2,720
EXPLORE

Jamaica to Antigua

12 Day Itinerary aboard Star Clipper
  • Swim in Montego Bay's waters
  • Explore Santo Domingo
  • Visit the Treasure Island
  • Hike Virgin Gorda trails
Starts / Ends:
Port Antonio / St. John's
Activities:
Local Market Visits, Small Ship Cruises, Snorkeling, Spa Relaxation
Activity Level:
Variable
Embark on a 12-day Caribbean cruise adventure from Jamaica to Antigua aboard Star Clipper. Explore historical sites like Rose Hall Great House or enjoy activities like snorkeling and zip-lining. Visit Port Antonio, a charming town with lush landscapes, secluded beaches, and attractions like Blue …
Cruise Details
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Farmer harvests his crop in Cuba
$3,390
EXPLORE

Cuba Walking Tour

8 Day Itinerary
  • Explore Cuba on foot
  • Snorkel in Zapata National Park
  • Learn about the tobacco industry
  • Hike to waterfalls and caves
  • Be immersed in Cuba's culture
  • Experience Cuban hospitality
Activities:
Hiking, Homestays, Local Market Visits, Snorkeling, Urban Exploration, Wildlife Viewing
Activity Level:
Moderate
Experience the diversity of Cuba on an 8-day guided Cuba tour. This People-to-People tour explores the diverse urban cities of Cienfuegos, Trinidad, and Havana and provides visitors incredible opportunities to delve into the rich traditions and heritage of Cuban culture. Hike pristine landscapes, …
Tour Details
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Havana Musicians
$2,245
EXPLORE

Classic Cuba

Cars, Rum, and Cigars - 5 Day Itinerary
  • Walk the vibrant streets of Havana
  • Sample rum and local delicacies
  • Tour cigar-rolling factories
  • Explore stunning Valley de Vinales
  • View Hemingway's former estate
Activities:
Hiking, Homestays, Local Market Visits, Urban Exploration
Activity Level:
Relaxed
Experience Classic Cuba on this 5-day Cars, Rum, and Cigars highlights tour. Encounter Hemingway's Havana as you visit his favorite bars and his former estate. Get a taste of Cuba's revolutionary spirit and contemporary culture with visits to Havana's Tropicana and Fábrica de …
Tour Details
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1-5 of 5 Results
TrustScore 4.9 | 313 reviews
TrustScore 4.9 of 5
total score
Based on 313 reviews on
review score
22 minutes ago
Excellent, friendly, and knowledgeable service and assistance.
Vaughna Cochenour
review score
5 hours ago
Was very easy to come up with an itinerary that included everything I wanted in a trip to Nepal with good communication, prompt service and really felt my needs were considered.
Robert
review score
7 hours ago
Jess was terrific and patiently guided us to make what we feel will be a wonderful family adventure.
David Herr
review score
14 hours ago
My family and I had been dreaming of going to Africa for two decades and our dream finally came true! I cannot begin to explain what an incredible experience we had working with Adventure Life, and specifically with Jason Maynard and his assistant Kriska Buison. From the deep knowledge of just about every activity, location and venue, to the patience and perseverance he had in working with us until we crafted the absolute perfect trip. We made a video that captures our experience, two of the most amazing weeks of our life... enjoy! To view it, you can go to YouTube and find my profile xdeanda and find my video "East Africa, summer 2024"
Xavier
review score
1 day ago
From the initial booking all the way through the trip, this was by far our favorite trip. Small boat travel is the only way to see a location. The excursions were so much more than I could explain. The locations were remote and awesome.
Lori I

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