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Select one of the below 12 best Greater Antilles trips for 2022 and 2023. Your local English speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Havana, Cienfuegos, Nassau, Playa Larga, and Trinidad. Our amazing trips to Greater Antilles for 2022 feature snorkeling, small ship cruises, kayaking, wildlife viewing, and homestays, and start from $1,499 for trips of 5 to 80 days. Most of the trips and itineraries below can be customized to meet your precise needs. Just contact one of Adventure Life's Greater Antilles trip planning experts to start planning your next seamless trip.
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Relax in the sunny squares of historic Savannah
$5,599
EXPLORE

Boston, MA to Nassau, Bahamas

16 Day Itinerary aboard Ocean Voyager
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts/ Ends in:
Boston / Nassau
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Relaxed
Sail on this 16-day itinerary cruising the seaboard from bustling Boston to beachy Nassau aboard Ocean Voyager. With stops in Baltimore, Charleston, West Palm Beach, and more, this journey has been handcrafted to sample the Eastern cities of the United States as you head to your final destination …
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Enjoy a ride around the islands.
$1,499
EXPLORE

Bahamas Sailing Adventure

7 Day Itinerary aboard Liberty Clipper
  • Explore the Out Islands
  • Learn how to sail and steer
  • Encounter unique wildlife
  • Kayak, snorkel, or paddle board
Starts/ Ends in:
Nassau / Nassau
Activities:
Kayaking, Sailing Schooner, Snorkeling, Stand Up Paddle Board, Wildlife Viewing
Activity Level:
Relaxed
Set sail for new horizons on a barefoot 7-day cruise in the Bahamas. On the 125-foot schooner, the tall ship Liberty Clipper, explore the Out Islands of the Bahamas from this majestic windjammer. Be welcomed aboard by expert crew who are there for your safety and enjoyment. From qualified Captains …
Cruise Details
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Relax on the sunny beaches of the Bahamas
$5,590
EXPLORE

Exploring the Bahamas’ Out Islands: Natural Wonders & Hidden History

Great Exuma, Bahamas Roundtrip - 8 Day Itinerary aboard National Geographic Sea Lion
  • Explore remote islands
  • Visit Conception National Park
  • Learn Bahamian history and culture
  • Kayak between mangroves
Starts/ Ends in:
George Town,The Exumas / George Town,The Exumas
Activities:
Kayaking, Small Ship Cruises, Snorkeling, Stand Up Paddle Boarding, Wildlife Viewing
Activity Level:
Relaxed
Discover the wild side of the Bahamas on a cruise to some of the country's most remote islands and hear an intriguing history of pirates, pilgrims, lost civilizations, and the slave trade. Snorkel in bright turquoise waters with an abundance of sea life, kayak through waterways, and take guided …
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Kayaking in Cuba
$3,190
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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:
Homestay, Kayaking, Land, 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 …
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Cycling through the revolutionary landscape of Cuba
$3,490
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Cuba Multisport

7 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 in:
Havana / Havana
Activities:
Biking, Hiking, Homestay, Kayaking, Land, Snorkeling, Wildlife Viewing
Activity Level:
Moderate
Experience Cuba by bike, kayak, and on foot on this 7-day guided Cuba multisport tour. This People-to-Peopletour 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 …
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Hiker in the Holguin Province, Cuba
$3,190
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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, Homestay, Land, Local Market, 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, …
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Farmer harvests his crop in Cuba
$2,245
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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, Homestay, Land, Local Market, 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 andFábrica de Arte …
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Relax on the beaches of the Caribbean
$6,180
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Christmas and New Year in the Caribbean

Fort-de-France - Santo Domingo - 13 Day Itinerary aboard Le Dumont-d'Urville
  • Explore gardens and parks
  • See UNESCO World Heritage Sites
  • Swim in crystal clear waters
  • Learn the history of the region
Starts/ Ends in:
Fort de France / Santo Domingo
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Board the luxurious Le Dumont-d'Urville to celebrate Christmas and ring in the New Year with this 13-day cruise. Set sail from Fort-de-France and cruise to some of the finest islands in the Caribbean. From the lush rainforest and mountainous terrain of Dominica, to the warm, clear waters of …
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Caribbean
$4,920
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Philipsburg Round Trip

8 Day Itinerary aboard Sea Cloud Spirit
  • Visit the port town of Philipsburg
  • Visit the birthplace of Sanjuaneros
  • Explore the famous ‘Love City’ Cruz
  • Discover the stunning White Bay
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Kayaking, Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board the Sea Cloud Spirit and start your exciting adventure from the beautiful city of Philipsburg, St. Maarten. Voyage along the idyllic and warm waters of the Caribbean and explore the beauty of each destination. Visit San Juan, Isla Culberita, and Esperanza in Puerto Rico. Explore the beautiful …
Cruise Details
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Explore colorful Gustavia
$5,760
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Santo Domingo and Caribbean treasures

Santo Domingo - Fort-de-France - 13 Day Itinerary aboard Le Dumont-d'Urville
  • Enjoy crystal waters of Caribbean.
  • Explore Santo Domingo.
  • Discover 8 islands on the same time
  • Amaze with landscapes of Guadeloupe
Starts/ Ends in:
Santo Domingo / Fort de France
Activities:
Hiking, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Board in Santo Domingo, where you can take in the charms of the "New World's" oldest capital, a UNESCO World Heritage Site. The British Virgin Islands are comprised of approximately sixty islands, most of which are uninhabited. They are located between the Lesser and Greater Antilles. …
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Visit historic Baltimore
$5,599
Savings
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Boston, MA to Nassau, Bahamas

16 Day Itinerary aboard Ocean Navigator
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts/ Ends in:
Boston / Nassau
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Relaxed
This 16-day tour takes you from lively Boston to the beaches of Nassau aboard the Ocean Navigator. With stops in Baltimore, Charleston, West Palm Beach, and other towns, this itinerary allows you to experience the Eastern cities of the United States en route to The Bahamas.
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Colorful canoes await passengers on the river
$40,499
EXPLORE

Grand Americas, Amazon & Antarctica

80 Day Itinerary aboard Seabourn Quest
  • Kayak in Antarctica to see wildlife
  • See Shackleton's grave in Grytviken
  • Enjoy Buzios' tropical beaches
  • See Brazil's Pink river dolphins
  • Explore Carambola beach clubs
Starts/ Ends in:
Miami / Miami
Activity Level:
Relaxed
Embark on an 80-day Grand Voyage aboard the Seabourn Quest to take in the amazing sights and diverse culture of the Americas, Amazon, and Antarctica.Reflect on the engineering marvel that is the Panama Canal as your ship sails majestically out of the canal and into the Pacific Ocean for your first …
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