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Top Caribbean Trips & Tours in October 2023

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Discover Caribbean in October 2023 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of Bridgetown, Havana, Cienfuegos, Trinidad, and Pinar del Río during October 2023 as you enjoy wildlife viewing, snorkeling, small ship cruises, homestays, and hiking. Prices for trips in October 2023 range from $2,245 to $16,186 for a vacation of 5 to 29 days. Choose any of the below 7 amazing itineraries in October 2023 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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Enjoy the clear blue waters of the Canary Islands
$4,060
EXPLORE

Ocean Crossing

Malaga-Barbados - 25 Day Itinerary aboard Star Clipper
  • Visit Malaga
  • Explore Casablanca
  • Discover Canary Islands
  • Enjoy Santa Cruz
Starts / Ends:
Malaga / Bridgetown
Activities:
Small Ship Cruises
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 fragrance. Embarking in the city of Malaga, …
Cruise Details
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Beautiful red bird, Scarlet Ibis, Eudocimus ruber in its typical environment
$9,151
EXPLORE

Caribbean and Brazilian Coasts

Philipsburg to Fortaleza - 13 Day Itinerary aboard SH Vega
  • Walk up to Fort Napoléon
  • Watch colorful exotic birds
  • Visit the Iles du Salut
  • See the spectacular sand dune
Starts / Ends:
Philipsburg / Fortaleza
Activities:
Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Set sail on an adventure that will introduce you to a superlative-defying part of the world. This 12-night Caribbean & Brazilian Coasts takes you from volcanic islands in the Caribbean Sea, along the northeastern coast of Brazil. Starting from Sint Maarten in the Lesser Antilles, you travel to …
Cruise Details
0
Cala d'Hort, Ibiza
$6,100
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
0
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 …
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, …
Tour Details
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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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Immerse yourself in the spectacular charm of the Atlantic Ocean
$2,770
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:
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 …
Cruise Details
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