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Top Caribbean Trips & Tours in May 2026

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Discover Caribbean in May 2026 on one of these 4 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2026 as you enjoy Local Market Visits, Village Visits, Archaeological Site Visits, Rainforest Exploration, and Snorkeling. Prices for trips in May 2026 range from $2,444 to $10,875 for a vacation of 8 to 10 days. Choose any of the below 4 itineraries in May 2026 and customize it when you contact one of Adventure Life's expert Caribbean trip planners.
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Areal view of Old city of Santo Domingo
from $2,443
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, Volunteering
Activity Level
Relaxed
Visit Dominican Republic and uncover hidden gems, from Jarabacoa coffee farms and cigar factories to coastal escapes in Punta Cana. Our tours include top-rated attractions, immersive cultural visits, and unforgettable nature experiences. Discover the best things to do in the Dominican Republic, from the capital to the coast.
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Cayo Arena Island
from $3,793
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
Activity Level
Easy Active
This 8-day journey will give you a genuine taste of the Dominican Republic. From UNESCO World Heritage Sites to street art and local delicacies, immerse yourself in the diverse landscapes and cultures of this Caribbean gem. With optional beach extensions, savor every moment of your unforgettable journey.
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Sunset view by the cliff houses
from $3,400
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
Village Visits, Ziplining, Hiking
Activity Level
Easy Active
Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day Dominican Republic trip, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.
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Deans Blue Hole
from $5,175
EXPLORE

West Caribbean Cruise

Belize - Fort Lauderdale - 10 Day Itinerary aboard SH Vega
  • Explore Belize City
  • Sail toward Grand Cayman
  • Swim with stingrays
  • Discover Montego Bay
Starts / Ends
Belize City / Fort Lauderdale
Activities
Local Market Visits, Archaeological Site Visits, Rainforest Exploration, Snorkeling, Wildlife Viewing, Helicopter Tours
Activity Level
Variable
Embark on an 10-day SH Vega cruise through the Western Caribbean. Explore Mayan ruins in Belize, relax on Grand Cayman's beaches, snorkel Montego Bay’s reefs, and visit Jamaica’s mountains. Enjoy birdwatching at Great Inagua, swim with sharks in the Exumas, and marvel at Nassau’s beauty.
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