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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 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
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Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
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.
  • Explore Antigua’s vibrant dockyards
  • Discover Les Saintes’ beaches
  • Relax on Martinique’s white sands
  • Stroll Grenada’s aromatic markets
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $9,990
2for1
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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
Bridgetown / Marigot
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.
  • Soak in Soufriere’s volcanic spring
  • Explore Les Saintes’ French charm
  • Visit Antigua’s Nelson’s Dockyard
  • Stroll Nevis’ Georgian towns
Cruise Details
0
Gustavia Harbor in St. Barths
from $9,990
2for1
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Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
Marigot / Marigot
Activities
Wildlife Viewing, Small Ship Sailing
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.
  • Explore Anguilla’s coral coastlines
  • Visit Virgin Gorda granite boulders
  • Discover Norman Island's coves
  • Relax on Anegada’s remote sands
Cruise Details
0
Explore beautiful Jost van Dyke
from $8,390
2for1
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Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
San Juan / St. John's
Activities
Local Market Visits
Activity Level
Variable
Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.
  • Discover Culebra Island’s shores
  • Explore Vieques Island waterfront
  • Tour St. John’s Annaberg ruins
  • Relax on Jost Van Dyke’s White Bay
Cruise Details
0
Sunset view by the cliff houses
from $3,237
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Dominican Republic: North Coast Expedition

8 Day Itinerary
Starts / Ends
Puerto Plata / Puerto Plata
Activities
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.
  • 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
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
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.
  • Visit UNESCO World Heritage sites
  • Visit Portsmouth, Dominica
  • Explore Les Saintes, Guadeloupe
  • See Mayreau's fishes and corals
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
Starts / Ends
Willemstad / Colon
Activities
Snorkeling, Village Visits, Hiking, 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.
  • 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
Cruise Details
0
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