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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 10 trips available for 2025 and 2026, 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 $2,020, 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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Dock going out into the crystal blue ocean
from $2,020
EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Explore Antigua’s vibrant dockyards
  • Discover Les Saintes’ beaches
  • Relax on Martinique’s white sands
  • Stroll Grenada’s aromatic markets
Starts / Ends
St. John's / Bridgetown
Activity Level
Variable
Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.
Cruise Details
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St Barts harbor view
from $7,990
2for1
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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
Urban Exploration, Local Market Visits
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
Cruise Details
0
Explore beautiful Jost van Dyke
from $7,740
2for1
EXPLORE

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
Kayaking, Adventure Options
Activity Level
Variable
Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz Bay’s scenic hikes, and Virgin Gorda’s famous Baths. Discover Philipsburg’s vibrant culture, Gustavia’s idyllic beaches, and Montserrat’s volcanic history.
Cruise Details
0
Sunset view by the cliff houses
from $3,237
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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
Wildlife Viewing, Ziplining, Rainforest Exploration
Activity Level
Easy Active
Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day adventure, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.
Tour Details
0
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 Cuba’s history may not have been made, but where it was lived every day. It reveals to you to Cuba’s true resource, its true legend: its people.
Tour Details
0
Relax on the shores of the Caribbean
from $6,800
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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 9 Day Itinerary aboard Le Bellot
  • Visit UNESCO World Heritage sites
  • Visit Portsmouth, Dominica
  • Explore Les Saintes, Guadeloupe
  • See Mayreau's fishes and corals
Starts / Ends
Les Saintes / Bridgetown
Activity Level
Variable
From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the Caribbean Sea. Before disembarking in Vieux Fort, explore long stretches of white-sand beaches, idyllic turquoise waters, and the laid-back island way of life.
Cruise Details
0
Ruins at the Fortress of Santiago
from $4,840
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Natural Sanctuaries & Heritage of the Caribbean

Willemstad - Colon - 8 Day Itinerary aboard Le Champlain
  • See sites in Cartagena & Willemstad
  • Explore Santa Marta & Sierra Nevada
  • Discover San Blas Islands' beaches
  • Visit and explore Fort San Lorenzo
  • Witness wildlife and ecosystems
Starts / Ends
Willemstad / Colon
Activities
Hiking, Snorkeling, Village Visits, Archaeological Site Visits
Activity Level
Variable
Explore the Caribbean on this 8-day Natural Sanctuaries & Heritage of the Caribbean cruise from Willemstad to Colon aboard the Le Champlain. Walk through UNESCO-listed cities, snorkel in the San Blas Islands, and meet the Kuna people. Visit Santa Marta’s mountains and the Fort San Lorenzo in Panama. Discover coral reefs, mangroves, and wildlife.
Cruise Details
0
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
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
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
0
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
0
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