Have questions? We're here.
Bright blue waters of the Caribbean sea

Caribbean Itineraries

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Join us on a trip to the Caribbean with our 8 diverse itineraries in 2025. Experience the enchanting blend of pristine beaches, vibrant cultures, and lush landscapes that define the Caribbean. Immerse yourself in the rhythmic beats of local music, savor the flavors of Caribbean cuisine, and explore the historical sites that tell tales of the region's rich past. Our itineraries offer opportunities for wildlife viewing, hiking through tropical forests, snorkeling in crystal-clear waters, and discovering hidden gems in charming villages. From the turquoise waters of the Bahamas to the lush rainforests of Costa Rica, our Caribbean tours provide a perfect mix of relaxation and adventure. Start your journey into the heart of the Caribbean with prices starting at $2,245 to $5,090 and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (8 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Caribbean
Kayaking in Cuba
$3,590
EXPLORE

Cuba Kayaking West Tour

8 Day Itinerary
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Activities:
Homestays, Kayaking, Snorkeling
Activity Level:
Easy Active
The world’s fascination with Cuba has lasted for many generations, and for good reason. Cuba is a cultural hub, with a mix of descendants of indigenous people, European immigrants, and slaves. The country's music and art draw from these diverse influences. Cuba has also exerted an …
Tour Details
0
Sunset view by the cliff houses
$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
Cayo Arena Island
$3,125
EXPLORE

Dominican Republic: Culture and Cocktails

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Visit coffee factory in Jarabacoa
  • Visit Los Pepines murals
  • Swim in azure waters of Cayo Arena
  • Visit cocoa & chocolate plantation
Starts / Ends:
Santo Domingo / Santo Domingo
Activities:
Archaeological Site Visits, Local Market Visits, Village Visits
Activity Level:
Easy Active
A mix of natural treasures, colonial history, rum, tobacco, cocoa, and coffee combine to craft a cocktail of unforgettable experiences. Explore UNESCO World Heritage Sites, vibrant neighborhoods bursting with street art and cuisine, and local producers showcasing the best of the Dominican Republic. …
Tour Details
0
Areal view of Old city of Santo Domingo
$2,612
EXPLORE

Best of Dominican Republic

8 Day Itinerary
  • Visit UNESCO site in Santo Domingo
  • Taste the culture and local food
  • Visit coffee factory in Jarabacoa
  • Learn about tobacco production
  • Visit cocoa & chocolate plantation
  • See the beaches of Las Terrenas
Starts / Ends:
Punta Cana / Punta Cana
Activities:
Hacienda Visits, Local Market Visits, Village Visits, Volunteering
Activity Level:
Relaxed
Explore the rich culture and breathtaking scenery of the Dominican Republic during this 8-day highlights journey. From Punta Cana, your trip starts on the vibrant streets of Santo Domingo, the capital city and the oldest European settlement in the Americas. Explore its UNESCO-listed Colonial Zone, …
Tour Details
0
Bicycle on Cuban street
$4,190
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
Cycling through the revolutionary landscape of Cuba
$3,690
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
Farmer harvests his crop in Cuba
$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
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
Havana Musicians
$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
1-8 of 8 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