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Top Caribbean Tours & Cruises in 2024

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Discover Caribbean in 2024 on one of these amazing trips hand selected by the travel experts at Adventure Life. Select any of the below 15 top-rated trips where you will explore Bridgetown, Gustavia, Soufriere, Fort de France, and Havana with an exceptional bilingual guide on a small group or customizable private tour. The most popular things to do in Caribbean in are cruises, snorkeling, small ship cruises, urban exploration, and wildlife viewing. Our Caribbean trips in 2024 range in price from $1,660 to $108,399 for trips of 5 to 80 days. Contact one of Adventure Life's expert Caribbean trip planners for help planning a seamless experience.
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White Sand Beach in Barbados
$1,660
EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Join the Royal Clipper on this 8-day cruise through theGrenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts,Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day.From the horseshoe-shaped Carenage at St. …
Cruise Details
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Relax in the sunny squares of historic Savannah
$8,389
EXPLORE

Boston, MA to Nassau, Bahamas

Boston - Nassau - 16 Day Itinerary aboard Ocean Voyager
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts / Ends:
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 …
Cruise Details
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Pelicans hanging out in the ocean
$11,590
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Stand on deck as Sea Cloud’s 30 white sails fill with wind, and measure the passage of time by a distant island’s approach on the horizon.Join thisextraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the …
Cruise Details
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Pink beach huts in the Caribbean
$1,660
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
Cruise Details
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Tropical waterfall and turquoise pool in lush forest
$2,400
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
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Beautiful beach in Dominica
$2,400
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this amazing region, there’s a lot of paradise to see. Best of all, …
Cruise Details
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Relax on the sunny beaches of the Caribbean
$4,480
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Explore the azure waters of Tobago
  • Observe the calm waters
  • Discover Eastern Caribbean
Starts / Ends:
Bridgetown / Marigot
Activities:
Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Cruise Eastern Caribbean with St. Barths on this 8-day adventure aboard Emerald Azzurra. Nature and culture aboundinn this mesmerizing tropical exploration of the eastern Caribbean. The azure waters of Tobago Cay National Park teem with wildlife just waiting to be discovered, while …
Cruise Details
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Explore colorful Gustavia
$4,510
EXPLORE

Hidden Charms of the Caribbean

San Juan - St John's - 8 Day Itinerary aboard Emerald Sakara
  • Discover active reefs in Culebra
  • Experience Vieques Island's charm
  • Indulge in Gustavia's French flair
  • Explore the serene Friars Beach
Starts / Ends:
San Juan / St. John's
Activities:
Urban Exploration, Village Visits
Activity Level:
Relaxed
Set sail on the Emerald Sakara, a contemporary luxury vessel, from San Juan and embark on an exciting Caribbean journey. Explore the diverse marine life and tranquil beaches of Culebra, the bustling waterfront of Esperanza Bay on Vieques Island, and the charming streets of Cruz Bay on St. John …
Cruise Details
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Enjoy Savannah's beautiful Forsyth Park
$5,909
EXPLORE

Roundtrip Jacksonville

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:
Jacksonville / Jacksonville
Activities:
Archaeological Site Visits, Small Ship Cruises, 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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Visit historic Baltimore
$8,389
EXPLORE

Boston, MA to Nassau, Bahamas

Boston - Nassau - 16 Day Itinerary aboard Ocean Navigator
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts / Ends:
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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Soufriere bay, St Lucia
$4,790
EXPLORE

Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Bellot
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts / Ends:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Bellot on this 9-day cruise combining long, white-sand beaches and the laid-back Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its garrison. Visit …
Cruise Details
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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:
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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Farmer harvests his crop in 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 …
Tour Details
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Colorful canoes await passengers on the river
$43,399
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:
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 …
Cruise Details
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