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Our Greater Antilles Trips & Vacation Packages

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Discover the vibrant and diverse Greater Antilles with our 17 unique trips for 2025. Join us on one of these top-rated vacation packages, carefully curated to showcase the rich cultural tapestry and stunning landscapes of this Caribbean region. From the historic streets of Havana to the lush jungles of the Dominican Republic, each adventure offers a mix of cultural immersion, wildlife viewing, and beach relaxation. Engage in local market visits, archaeological site explorations, and snorkeling excursions, all while surrounded by the natural beauty that defines the Greater Antilles. Whether you're interested in food & wine experiences, urban exploration, or active adventures like hiking and kayaking, there's something for every type of traveler on these trips. With trips ranging from 5 to 13 days in length, there's no better time to start planning your next Caribbean getaway. Contact one of our Caribbean specialists for help planning your next seamless trip.
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    • Greater Antilles
Kayaking in Cuba
$3,590
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
0
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
0
Bicycle on Cuban street
$4,190
EXPLORE

Cuba Cycling Tour

Quintessential Cuba - 8 Day Itinerary
  • Cycle through western Cuba
  • Visit Hemingway's former home
  • Ride through Cuba's tobacco fields
  • Explore Havana on foot
Activities:
Biking, Hiking
Activity Level:
Moderate
Cuba creates legends and imbues folklore. Everyday items such as a rolled cigar, a glass of rum spiked with sugarcane juice, a colorful classic car become more—gain a near-mythical status and a story that endured in the American consciousness even when Cuba’s doors were closed. Join …
Tour Details
0
Big brown pelicans at the Florida Keys
$9,635
EXPLORE

Insider Tip for Sailing Enthusiast

10 Day Itinerary aboard Sea Cloud Spirit
  • Experience culture and museum visit
  • Explore beaches and marine life
  • Experience Key West culture
  • Enjoy exclusive ship amenities
Starts / Ends:
Miami / Miami
Activities:
Adventure Options, Snorkeling
Activity Level:
Variable
Embark on a 10-day Caribbean adventure from Miami to the Bahamas' most exclusive islands, where you'll explore vibrant Miami's cosmopolitan atmosphere before setting sail to serene Eleuthera, with its dreamy pink beaches and lush nature reserves. Then, discover the exclusive paradise of …
Cruise Details
0
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
0
Cayo Arena Island
$3,125
EXPLORE

Dominican Republic: Culture and Cocktails

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Visit coffee factory in Jarabacoa
  • Visit Los Pepines murals
  • Swim in azure waters of Cayo Arena
  • Visit cocoa & chocolate plantation
Starts / Ends:
Santo Domingo / Santo Domingo
Activities:
Archaeological Site Visits, Local Market Visits, Village Visits
Activity Level:
Easy Active
A mix of natural treasures, colonial history, rum, tobacco, cocoa, and coffee combine to craft a cocktail of unforgettable experiences. Explore UNESCO World Heritage Sites, vibrant neighborhoods bursting with street art and cuisine, and local producers showcasing the best of the Dominican Republic. …
Tour Details
0
Cycling through the revolutionary landscape of Cuba
$3,690
EXPLORE

Cuba Multisport

8 Day Itinerary
  • Bike, kayak, snorkel, and hike Cuba
  • Appreciate Cuba's colonial past
  • Be immersed in Cuba's culture
  • Enjoy excellent wildlife viewing
  • Experience Cuban hospitality
Starts / Ends:
Havana / Havana
Activities:
Biking, Hiking, Homestays, Kayaking, Snorkeling, Wildlife Viewing
Activity Level:
Moderate
Experience Cuba by bike, kayak, and on foot on this 8-day guided Cuba multisport tour. This People-to-People tour offers myriad opportunities to delve into Cuba's rich traditions, from architecture to lively music and authentic cuisine, and enjoy meaningful exchanges with Cubans. Learn about …
Tour Details
0
Deans Blue Hole
$4,380
EXPLORE

West Caribbean Cruise

Belize - Fort Lauderdale - 11 Day Itinerary aboard SH Vega
  • Witness Bahama's pinkest flamingo
  • Swim with nurse sharks in Exuma
  • Snorkel vibrant coral reefs
  • Visit Cockscomb wildlife sanctuary
Starts / Ends:
Belize City / Fort Lauderdale
Activities:
Rainforest Exploration, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Set sail aboard the SH Vega for an 11-day Western Caribbean adventure. Explore Belize City’s Mayan ruins at Lamanai and the jaguar sanctuary in Cockscomb Basin. Snorkel in Grand Cayman at Stingray City and unwind on the award-winning Seven Mile Beach. Experience Montego Bay’s vibrant …
Cruise Details
0
Farmer harvests his crop in Cuba
$3,590
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
0
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
0
Explore the famous rock formations of the baths
$7,500
EXPLORE

A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore Old San Juan's forts
  • Enjoy salsa music
  • Sail in the British Virgin Islands
  • Explore unique rock formations
Starts / Ends:
San Juan / San Juan
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Join an 8-day Caribbean journey starting in San Juan, where the city's enduring strength against historic invasions shines through its monumental forts—La Fortaleza, Fort San Felipe del Morro, Fort San Juan de la Cruz, and Fort San Cristóbal—guarding UNESCO World …
Cruise Details
0
Nassau Lighthouse
$23,390
EXPLORE

Island Odyssey: Bahamas to the Grenadines

Nassau - Bridgetown - 13 Day Itinerary aboard Scenic Eclipse
  • Explore beaches on Compass Cay
  • See swimming pigs on Exuma Island
  • Discover Long Island on foot
  • Enjoy the view from Gorda Point
Starts / Ends:
Nassau / Bridgetown
Activities:
Hiking, Small Ship Cruises, Snorkeling
Activity Level:
Variable
Embark on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Sail to Compass Cay and explore its pristine beaches, snorkel in crystal-clear waters, or spot marine life from the marina. Discover the hidden gem of Great Exuma Island, with its …
Cruise Details
0
Areal view of Old city of Santo Domingo
$2,612
EXPLORE

Best of Dominican Republic

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Taste the culture and local food
  • Visit coffee factory in Jarabacoa
  • Learn about tobacco production
  • Visit cocoa & chocolate plantation
  • See the beaches of Las Terrenas
Starts / Ends:
Punta Cana / Punta Cana
Activities:
Hacienda Visits, Local Market Visits, Village Visits, Volunteering
Activity Level:
Relaxed
Explore the rich culture and breathtaking scenery of the Dominican Republic during this 8-day highlights journey. From Punta Cana, your trip starts on the vibrant streets of Santo Domingo, the capital city and the oldest European settlement in the Americas. Explore its UNESCO-listed Colonial Zone, …
Tour Details
0
Explore the famous rock formations of the baths
$7,990
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
Explore beautiful Jost van Dyke
$7,190
EXPLORE

Caribbean Yachting Hideaways

St Thomas - St John's - 8 Day Itinerary aboard Emerald Azzurra
  • Visit The Baths’ granite formation
  • Explore Culebra's white-sand beach
  • Experience swimming off the yacht
  • Discover the history of St. John
Starts / Ends:
St. Thomas / Antigua
Activities:
Adventure Options, Hiking, Kayaking, Snorkeling
Activity Level:
Variable
Experience an 8-day Caribbean journey aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches and vibrant reefs, then sail to Vieques for its beautiful waterfront and Sun Bay. Discover Cruz Bay on St. John with its charming town and scenic hikes. Experience the natural …
Cruise Details
0
St Barts harbor view
$10,490
EXPLORE

Caribbean Yachting Discovery

8 Day Itinerary aboard Emerald Azzurra
  • Visit Botanical Garden in Deshaies
  • Relax on Barbuda’s pink-sand beach
  • Discover vibrant town of Gustavia
  • Explore St. Barts’ vibrant streets
Starts / Ends:
St. John's / San Juan
Activities:
Adventure Options, Hiking, Local Market Visits, Snorkeling, Urban Exploration
Activity Level:
Variable
Cruise the Caribbean for 8 days aboard Emerald Azzurra. Discover Barbuda’s pink-sand beaches and the renowned Frigate Bird Sanctuary. Explore Îles des Saintes with its historic Fort Napoleon and vibrant culture. Visit Deshaies, known for its Creole architecture and lush botanical …
Cruise Details
0
A dish created by Chef Ben Robinson
$6,966
EXPLORE

Caribbean Yachting Discovery with Chef Ben Robinson

8 Day Itinerary aboard Emerald Azzurra
  • Visit Botanical Garden in Deshaies
  • Relax on Barbuda’s pink-sand beach
  • Discover vibrant town of Gustavia
  • Explore St. Barts’ vibrant streets
Starts / Ends:
St. John's / San Juan
Activities:
Adventure Options, Hiking, Local Market Visits, Snorkeling, Urban Exploration
Activity Level:
Variable
Embark on this 8-day Caribbean cruise with Chef Ben Robinson aboard the Emerald Azzurra. Start with a welcome reception, join an interactive cooking demo to recreate one of Chef Ben’s dishes, and enjoy his signature multi-course dinner and other special dishes throughout the week. Experience …
Cruise Details
0
1-17 of 17 Results
TrustScore 4.8 | 393 reviews
TrustScore 4.8 of 5
total score
Based on 393 reviews on
review score
4 days ago
The Adventure Life staff, for me it's Franny, always listens to what I say about what kind of travel my wife and I want and expect. It never goes wrong. The motto at AL seems to be I will get back to you right away if not sooner. Requested changes and special requests are encouraged and acted on ASAP.
Dick Philpot
review score
6 days ago
The trip planners at Adventure Life were very helpful and always replied to my inquiries right away. The excursions, accomodations, and local guides were excellent
Avi Argaman
review score
1 week ago
Be sure to sign up for all the tours, otherwise you will be sitting on the boat since not all stops are moored at a dock. Some are anchored.
Gail Puryear
review score
1 week ago
There were two best aspects to our trip: 1. The Adventure Life folks and the folks in Athens and Crete who supported our itinerary, guided us, and ran the cooking program were all superb. 2. Everything they all planned for us went without a hitch. When we needed a bit of help, they came through with really good answers. We became aware of AL from a friend who had an excellent experience in a different location. So did we. We can recommend AL without reservation.
Tom Campbell
review score
1 week ago
My agent Jeff did not push the sale while providing thorough information and replying quickly to my many questions.
Mary Lou Carlson

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