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Top Caribbean Trips & Tours in October 2022

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Discover Caribbean in October 2022 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of Havana, Cienfuegos, Trinidad, Playa Larga, and Bridgetown during October 2022 as you enjoy homestays, snorkeling, small ship cruises, hiking, and urban exploration. Prices for trips in October 2022 range from $2,245 to $13,380 for a vacation of 5 to 29 days. Choose any of the below 7 amazing itineraries in October 2022 and customize it to make it your own with the help of one of Adventure Life's expert Caribbean trip planners.
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Relax in the sunny squares of historic Savannah
$5,599
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 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 …
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 …
Tour Details
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Cala d'Hort, Ibiza
$5,960
EXPLORE

Westbound Atlantic Ocean Crossing

Cannes to Barbados - 29 Day Itinerary aboard Royal Clipper
  • Marvel at Bonifacio's views
  • Explore charming Mahon, Menorca
  • See Malaga's Moorish architecture
  • Enjoy Marbella's natural beauty
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Experience the uninhibited thrill of traversing a boundless ocean under sail, without any skills or effort required on your part. Imagine long lazy days at sea chasing the horizon, relaxing under a blanket of stars and taking in the ocean's salty fragance. Embarking in the city of Cannes, this …
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 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 …
Tour Details
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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 …
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Immerse yourself in the spectacular charm of the Atlantic Ocean
$2,690
EXPLORE

Westbound Atlantic Ocean Crossing

Lisbon to Barbados - 17 Day Itinerary aboard Royal Clipper
  • Discover Lisbon and its history
  • Visit Safi, Morocco
  • View Tenerife's mountains
  • Enjoy the beaches of Barbados
Starts/ Ends in:
Lisbon / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
The 439-foot Royal Clipper is the ultimate sea-going experience for sail cruising enthusiasts, combining the grandeur, adventure, and tradition of sailing with the superior service, amenities, and accommodations of the finest modern yacht. Swim and snorkel in the Caribbean Sea's pristine …
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