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Top Caribbean Trips & Tours in May 2025

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Discover Caribbean in May 2025 on one of these 8 tours hand-selected by the travel experts at Adventure Life. Explore the best of Havana, Santiago de los Caballeros, Pinar del Río, Viñales, and Punta Rucia during May 2025 as you enjoy land tours, cultural, hiking, local market visits, and wildlife viewing. Prices for trips in May 2025 range from $2,238 to $7,280 for a vacation of 5 to 11 days. Choose any of the below 8 itineraries in May 2025 and customize it when you contact one of Adventure Life's expert Caribbean trip planners.
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Sunset view by the cliff houses
$2,287
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
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Cayo Arena Island
$2,850
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
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Areal view of Old city of Santo Domingo
$2,237
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
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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:
Relaxed
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
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Deans Blue Hole
$3,580
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West Caribbean Cruise

Belize - Fort Lauderdale - 11 Day Itinerary aboard SH Vega
  • Witness Bahama's pinkest flamingo
  • Swim with nurse sharks in Exuma
  • Snorkel vibrant coral reefs
  • Visit Cockscomb wildlife sanctuary
Starts / Ends:
Belize City / Fort Lauderdale
Activities:
Rainforest Exploration, Snorkeling, Wildlife Viewing
Activity Level:
Variable
Set sail aboard the SH Vega for an 11-day Western Caribbean adventure. Explore Belize City’s Mayan ruins at Lamanai and the jaguar sanctuary in Cockscomb Basin. Snorkel in Grand Cayman at Stingray City and unwind on the award-winning Seven Mile Beach. Experience Montego Bay’s vibrant …
Cruise Details
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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
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Farmer harvests his crop in Cuba
$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
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
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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
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