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Caribbean Hiking Trips

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Experience the Caribbean's unique beauty and culture on a hiking trip with Adventure Life. From the rolling hills of Jamaica to the lush rainforests of Puerto Rico, this region is a paradise for trekkers. With 7 trips available for 2026 and 2027, you can explore vibrant cities, unspoiled beaches, and some of the world's most spectacular mountain peaks. No matter where you go, every journey promises unparalleled views, fascinating wildlife encounters, and unforgettable memories. Our Caribbean hiking trips start at $2,245, ensuring your safety and comfort while preserving the natural environment in a responsible way. From rugged coastlines to misty mountain trails, let Adventure Life show you why this incredible region is one of our favorite destinations! Start planning your next seamless trip today with one of our Caribbean hiking specialists. Contact us to learn more.
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Gustavia Harbor in St. Barths
from $9,990
EXPLORE

Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Anguilla’s coral coastlines
  • Visit Virgin Gorda granite boulders
  • Discover Norman Island's coves
  • Relax on Anegada’s remote sands
Starts / Ends
Marigot / Marigot
Activities
Hiking, Wildlife Viewing, Snorkeling
Activity Level
Variable
Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
Cruise Details
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Sunset view by the cliff houses
from $3,400
EXPLORE

Dominican Republic: North Coast Expedition

8 Day Itinerary
  • Enjoy canyoning in Puerto Plata
  • See the landscape using 4x4 buggy
  • Visit the Los Pepines murals.
  • Learn about tobacco production
  • See the lovely bay of Rio San Juan
  • Zip line over the Laguna Dudu
Starts / Ends
Puerto Plata / Puerto Plata
Activities
Local Market Visits, Village Visits, Ziplining, Rainforest Exploration
Activity Level
Easy Active
Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day Dominican Republic trip, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.
Tour Details
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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
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
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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, Kayaking
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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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
Homestays, Urban Exploration
Activity Level
Relaxed
Rolled cigars, rum spiked with sugarcane juice, and colorful vintage cars - these are the icons of Cuba that await you on this 5-day People-to-People classic Cuba tour. Find yourself immersed in legendary Cuban culture as you explore legendary Havana, the tobacco mecca Vuelta Abajo, and breathtaking Valle de Viñales.
Tour Details
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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
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.
Tour Details
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Relax on the sunny beaches of the Caribbean
from $9,990
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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
  • Soak in Soufriere’s volcanic spring
  • Explore Les Saintes’ French charm
  • Visit Antigua’s Nelson’s Dockyard
  • Stroll Nevis’ Georgian towns
Starts / Ends
Bridgetown / Marigot
Activities
Archaeological Site Visits
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
Cruise Details
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