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Greater Antilles Hiking Trips

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Explore the Caribbean's Greater Antilles with Adventure Life on one of these 6 extraordinary hiking trips for 2025 and 2026. From the lush rainforests of Puerto Rico to the paradisiacal beaches of Cuba, this region offers a stunningly diverse landscape. Hike through verdant mountains, meandering rivers, and hidden waterfalls while immersing yourself in centuries-old cultures. Visit destinations like Havana, Viñales, Topes de Collantes, Gustavia, and Pinar del Río, where history comes alive in colonial cities and vibrant local markets. On each trail, you'll be rewarded with spectacular views and a deeper understanding of nature's beauty. Our Greater Antilles hiking trips start at $2,245 for adventures lasting up to 5 to 8 days days. Adventure Life ensures your safety, comfort, and enjoyment while revealing this unique part of the world in a responsible and sustainable way. Contact one of our tour specialists today to help plan your next seamless trip!
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Bicycle on Cuban street
from$4,390
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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
Activities:
Biking, Hiking
Activity Level:
Moderate
Cuba creates legends and imbues folklore. Everyday items such as a rolled cigar, a glass of rum spiked with sugarcane juice, a colorful classic car become more—gain a near-mythical status and a story that endured in the American consciousness even when Cuba’s doors were closed. Join …
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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:
Biking, Hiking, Homestays, Kayaking, Snorkeling, Wildlife Viewing
Activity Level:
Moderate
Experience Cuba by bike, kayak, and on foot on this 8-day guided Cuba multisport tour. This People-to-People tour 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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Havana Musicians
from$2,245
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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, Homestays, Local Market Visits, 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 and Fábrica de …
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Farmer harvests his crop in Cuba
from$3,590
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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:
Hiking, Homestays, Local Market Visits, 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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Explore beautiful Jost van Dyke
from$7,740
2-for-1
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Caribbean Yachting Hideaways

St Thomas - St John's - 8 Day Itinerary aboard Emerald Azzurra
  • Visit The Baths’ granite formation
  • Explore Culebra's white-sand beach
  • Experience swimming off the yacht
  • Discover the history of St. John
Starts / Ends:
St. Thomas / Antigua
Activities:
Adventure Options, Hiking, Kayaking, Snorkeling
Activity Level:
Variable
Experience an 8-day Caribbean journey aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches and vibrant reefs, then sail to Vieques for its beautiful waterfront and Sun Bay. Discover Cruz Bay on St. John with its charming town and scenic hikes. Experience the natural …
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St Barts harbor view
from$7,990
2-for-1
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Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Barbuda's pink beaches
  • Discover Deshaies’ architecture
  • Visit Gustavia’s charming boutiques
  • Experience Virgin Gorda’s baths
Starts / Ends:
St. John's / San Juan
Activities:
Hiking, Local Market Visits, Urban Exploration
Activity Level:
Variable
Embark on an 8-day cruise aboard the Emerald Azzurra, beginning in Antigua, an island celebrated for its rich history and stunning beaches. Sail to Barbuda, where tranquil pink-sand beaches and crystal-clear waters await. Explore Iles des Saintes, a picturesque archipelago renowned for its …
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