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Caribbean Bicycling Tours & Trips

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Venture off the beaten path with Adventure Life and explore the Caribbean on two wheels! From its lush tropical forests to its pristine white sand beaches, this region is a paradise for cyclists. 2 cycling trips in 2026 and 2027 give you the chance to experience some of the islands' most incredible sights without compromising your safety, comfort, or sense of adventure. Ride past secluded waterfalls in Jamaica, discover historical sites and vibrant coral reefs in The Bahamas, or take a journey through colonial cities like Cartagena de Indias. With Adventure Life's comprehensive knowledge and expertise, our cycling trips are designed to be seamless experiences that let you immerse yourself in local culture while exploring breathtaking scenery. Our Caribbean biking trips start at $3,890, for expeditions ranging from 8 days days. Discover what lies beyond the horizon with Adventure Life - contact one of our tour specialists today for help planning your next seamless trip!
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Bicycle on Cuban street
from $4,390
EXPLORE

Cuba Cycling Tour

Quintessential Cuba - 8 Day Itinerary
  • Cycle through western Cuba
  • Visit Hemingway's former home
  • Ride through Cuba's tobacco fields
  • Explore Havana on foot
Activity Level
Moderate
A cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where the island's rich history isn't just remembered—it is lived every day. It reveals Cuba’s greatest resource and truest legend: its people.
Tour Details
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Cycling through the revolutionary landscape of Cuba
from $3,890
EXPLORE

Cuba Multisport

8 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
Hiking, Biking, Wildlife Viewing, Kayaking, Homestays, Snorkeling
Activity Level
Moderate
Explore the intriguing island of Cuba on this active 8-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil countryside. Experience great colonial cities including Havana, Cienfuegos, Trinidad, and Sancti Spiritus. Discover Cuba's history, rich traditions, and dynamic present on this Cuba multisport trip.
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