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Top Greater Antilles Tours & Trips in 2022

Travel made your way
Greater Antilles
  • 14 Cruises + Land Tours
Picturesque Cuba
Caribbean
  • 37 Cruises + Land Tours
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Clear waters of the Caribbean sea
Antigua
  • 6 Cruises
Lush green forests and clear blue waters of the Caribbean
Barbados
  • 10 Cruises
Take a leisurely stroll through beautiful Bridgetown
Dominica
  • 8 Cruises
Encounter tropical wildlife while you sail on the Aranui
Grenada
  • 11 Cruises
Snorkel the clear, tropical waters
Lesser Antilles
  • 28 Cruises
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
Puerto Rico
  • 2 Cruises
Discover incredible history and culture in Puerto Rico
Lesser Antilles
  • 28 Cruises
Wander the white-sand beaches of St. Johns on your Virgin Islands cruise
St. Barth
  • 9 Cruises
Play on the famously beautiful beaches of St. Barth's
St. Kitts
  • 4 Cruises
Stroll along the beautiful beaches of the Caribbean
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    • Greater Antilles
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 Sites, Small Ship Cruise, Urban Exploration, Village Visit
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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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 Cruise, Snorkeling, Stand Up Paddle Board, Wildlife Viewing
Activity Level:
Relaxed
Discover the Bahamas’ wild side on a voyage to some of its most far-flung islands and hearan intriguing history of pirates, pilgrims,lost civilizations,and the slave trade.Snorkel with abundant sea life inwarm turquoise waters, explore waterways by kayak, and get introduced to the …
Cruise Details
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Enjoy a ride around the islands.
$1,399
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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Kayaking in Cuba
$3,190
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:
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
EXPLORE

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
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, 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
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, 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
EXPLORE

Christmas and New Year in the Caribbean

Fort-de-France - Santo Domingo - 14 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 Cruise, Snorkeling
Activity Level:
Relaxed
Board the luxurious Le Dumont-d'Urville to celebrate Christmas and ring in the New Year with this 14-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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Enjoy Savannah's beautiful Forsyth Park
$4,699
EXPLORE

Southern Coastal Charm

Roundtrip Amelia Island - 12 Day Itinerary aboard Ocean Voyager
  • Experience Jacksonville hospitality
  • Explore beautiful Savannah, Georgia
  • Admire Charleston's architecture
  • Sunbathe on beaches in the Bahamas
Starts/ Ends in:
Jacksonville / Amelia Island
Activities:
Archaeological Sites, Small Ship Cruise, Urban Exploration
Activity Level:
Relaxed
From the historic South to pristine beaches, a voyage from the Southeast coast to The Bahamas delivers just the right balance of excitement and relaxation. Charleston, South Carolina, and Savannah, Georgia offer a glimpse into coastal Southern living and stunning historic architecture, while the …
Cruise Details
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Caribbean
$5,350
EXPLORE

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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Relax on the sunny beaches of the Bahamas
$4,140
EXPLORE

Bridgetown to Fort Lauderdale

9 Day Itinerary aboard Silver Wind
  • See Conception Island's wildlife
  • Visit Devil’s Bay National Park
  • Marvel at Barbuda's frigatebirds
  • Dip in the hot springs of Roseau
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Experience the Caribbean as never before during this 9-day cruise from Bridgetown to Fort Lauderdale. Spend time relaxing on white sandy beaches and enjoying coral reefs and the warm, clear waters of islands such as Dominica, St. Vincent and Antigua. But the Caribbean is so much more: tiny, off the …
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Explore colorful Gustavia
$5,440
EXPLORE

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 Cruise, 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. …
Cruise Details
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Visit historic Baltimore
$5,599
EXPLORE

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 Sites, Small Ship Cruise, Urban Exploration, Village Visit
Activity Level:
Relaxed
Sail on this 16-day itinerary cruising the seaboard from bustling Boston to beachy Nassau aboard Ocean Navigator. 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 …
Cruise Details
0
1-13 of 13 Results

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