Currency (USD)
|
Log In
Email
Password Forgot Password
Sign in with GoogleSign in with Google
|
Favorites
Have questions? We're here.
Bright blue waters of the Caribbean sea

Caribbean Hiking Trips

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
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 11 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.
Filter (11 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Caribbean
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
Activities:
Hiking, Local Market Visits, Small Ship Cruises, Snorkeling, Village Visits, Wildlife Viewing
Activity Level:
Variable
Embark on an 8-day cruise aboard the Royal Clipper, starting in Antigua, the vibrant hub of yachting culture. Explore the pristine beaches and underwater wonders of Les Saintes, followed by Dominica’s lush rainforests, Trafalgar Falls, and a bubbling lake. Bask on Martinique’s idyllic …
Cruise Details
0
St Barts harbor view
from$7,990
2-for-1
EXPLORE

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 …
Cruise Details
0
A dish created by Chef Ben Robinson
from$6,966
2-for-1
EXPLORE

Caribbean Yachting Discovery with Chef Ben Robinson

8 Day Itinerary aboard Emerald Azzurra
  • Visit Botanical Garden in Deshaies
  • Relax on Barbuda’s pink-sand beach
  • Discover vibrant town of Gustavia
  • Explore St. Barts’ vibrant streets
Starts / Ends:
St. John's / San Juan
Activities:
Adventure Options, Hiking, Local Market Visits, Snorkeling, Urban Exploration
Activity Level:
Variable
Embark on this 8-day Caribbean cruise with Chef Ben Robinson aboard the Emerald Azzurra. Start with a welcome reception, join an interactive cooking demo to recreate one of Chef Ben’s dishes, and enjoy his signature multi-course dinner and other special dishes throughout the week. Experience …
Cruise Details
0
Explore colorful Gustavia
from$6,340
2-for-1
EXPLORE

Caribbean Enchantment

7 Day Itinerary aboard Emerald Azzurra
  • Visit Botanical Garden in Deshaies
  • Visit Fort Napoleon on Les Saintes
  • Visit The Baths on Virgin Gorda
  • Explore St. Barts’ vibrant streets
Starts / Ends:
St. John's / Marigot
Activities:
Adventure Options, Hiking, Local Market Visits, Snorkeling, Urban Exploration
Activity Level:
Variable
Embark on a 7-day Caribbean cruise aboard Emerald Azzurra. Start in Antigua and sail to Les Saintes, a French-Caribbean archipelago with picturesque towns and the historic Fort Napoleon. Discover Deshaies in Guadeloupe, known for its colorful Creole architecture and beautiful beaches. Visit Virgin …
Cruise Details
0
Sunset view by the cliff houses
from$3,237
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:
Hiking, Local Market Visits, Rainforest Exploration, Snorkeling, Village Visits, Wildlife Viewing, Ziplining
Activity Level:
Easy Active
Experience the wild, rugged beauty of the north coast of the Dominican Republic on this 8-day adventure expedition. Indulge in canyoning, buggy riding, and ziplining for an adrenaline rush. Immerse yourself in nature with trips through mangroves to Paradise Island, swims in lagoons, and cave …
Tour Details
0
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
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 …
Tour Details
0
Relax on the shores of the Caribbean
from$6,400
EXPLORE

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
Activities:
Hiking, Small Ship Cruises, Snorkeling, Village Visits, Wildlife Viewing
Activity Level:
Variable
Embark on a 9-day cruise aboard Le Bellot, exploring the Caribbean's most enchanting islands. This itinerary blends pristine white-sand beaches, turquoise waters, and the relaxed rhythm of island life. Begin in Vieux Fort, St. Lucia, where the iconic Gros and Petit Pitons rise dramatically as …
Cruise Details
0
Enjoy the beautiful blue Caribbean
from$6,830
EXPLORE

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 9 Day Itinerary aboard Le Champlain
  • Explore Portsmouth’s mountains
  • Visit Les Saintes’ beaches
  • Snorkel Port Elizabeth’s waters
  • Discover Grenada’s spice island
Starts / Ends:
Les Saintes / Bridgetown
Activities:
Hiking, Small Ship Cruises, Snorkeling, Village Visits
Activity Level:
Variable
Embark on a 9-day cruise aboard Le Champlain, exploring the enchanting islands of the Caribbean. This itinerary combines pristine white-sand beaches, crystal-clear turquoise waters, and the relaxed charm of island life. Begin in Vieux Fort, St. Lucia, where the iconic volcanic peaks, Gros and Petit …
Cruise Details
0
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:
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 …
Tour Details
0
Havana Musicians
from$2,245
EXPLORE

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 …
Tour Details
0
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:
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, …
Tour Details
0
1-11 of 11 Results

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By