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Active Adventures in Caribbean

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Join us on one of these 5 Caribbean active adventure tours in 2026. Customize your Caribbean adventure with visits to Cienfuegos, Havana, Playa Larga, Topes de Collantes, and Trinidad and combine the perfect mix of Snorkeling, Hiking, Homestays, Kayaking, and Local Market Visits to accommodate any fitness and skill level. Contact one of our Caribbean adventure travel planners for help planning your next trip.
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Panoramic views on the climb to Pico Duarte
from $2,299
EXPLORE

Mountain Adventure in the Caribbean Highlands

Self Drive Tour - 8 Day Itinerary
  • Trek to the Pico Duarte summit
  • Hike to towering waterfalls
  • Explore the historic Zona Colonial
  • Rappel down into lush canyons
  • Drive steep mountain roads
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Hiking, Ziplining, Camping
Activity Level
Challenging
Pick up your 4x4 and set off into the Dominican Republic's central mountains for an active 8-day adventure. You drive over high mountain passes, explore coffee plantations, and rappel down canyons. The trip culminates in a challenging 2-day trek to the summit of Pico Duarte, the highest peak in the Caribbean.
Tour Details
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Kayaking in Cuba
from $3,590
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
Activity Level
Easy Active
Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.
Tour Details
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Beautiful beach in Dominica
from $8,370
EXPLORE

Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
  • Relax on Grande Anse Beach
  • Snorkel Tobago Cays Reefs
  • Visit Port Elizabeth waterfront
  • Discover Portsmouth landscapes
Starts / Ends
Anses d'Arlet / Marie Galante
Activities
Snorkeling, Local Market Visits, Village Visits, Scuba Diving
Activity Level
Variable
Explore Guadeloupe and the Southern Caribbean aboard Le Ponant on an 8-day cruise. Swim in Tobago Cays, snorkel at Sandy Island, discover Grande Anse d’Arlet, visit Portsmouth, sail past The Pitons, and experience Creole culture, beaches, reefs, and island towns across multiple Caribbean destinations.
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Cycling through the revolutionary landscape of Cuba
from $3,890
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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
Kayaking, Biking
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.
Tour Details
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Farmer harvests his crop in Cuba
from $3,590
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
Starts / Ends
Havana / Havana
Activities
Homestays, Wildlife Viewing, Urban Exploration
Activity Level
Moderate
Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, Vinales, Havana, and five parks & reserves. Explore by foot and encounter local experts, farmers, and artists as you gain insight into their history, traditions & vibrant culture on this highlights Cuba trip.
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Jeff Rottschafer Adventure Life employee profile
Jeff R.
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