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Top Caribbean Trips & Tours in May 2024

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Discover Caribbean in May 2024 on one of these 8 tours hand-selected by the travel experts at Adventure Life. Explore the best of Havana, Trinidad, Cienfuegos, Playa Larga, and Viñales during May 2024 as you enjoy hiking, snorkeling, cultural, land tours, and homestays. Prices for trips in May 2024 range from $2,245 to $12,999 for a vacation of 5 to 24 days. Choose any of the below 8 itineraries in May 2024 and customize it when you contact one of Adventure Life's expert Caribbean trip planners.
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Kayaking in Cuba
$3,390
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
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Sunset over Philipsburg
$4,499
EXPLORE

Island Hopper

Bridgetown - Philipsburg - 8 Day Itinerary aboard World Voyager
  • Discover and Relax
  • Enjoy beaches and water sports
  • Dive shipwrecks and explore coasts
  • Sample famous and local rum
Starts / Ends:
Bridgetown / Philipsburg
Activities:
Hiking, Snorkeling
Activity Level:
Relaxed
Embark on a natural marvels journey at Rodney Bay's awe-inspiring Piton Mountains. Les Trois-Îlets, born from Le Diamant, les Anses-d'Arlet, and Sainte-Luce, offers lush forests beyond beaches. Discover Carambola Beach's tranquility near Brimstone Hill Fortress, a historic marvel. …
Cruise 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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Take a leisurely stroll through beautiful Bridgetown
$6,999
EXPLORE

Mystique of the Azores

Bridgetown - Lisbon - 14 Day Itinerary aboard World Voyager
  • Explore Azores Islands
  • Experience Ponta Delgada
  • Stroll Praia da Vitória
  • Hike Vigia da Queimada
Starts / Ends:
Bridgetown / Lisbon
Activities:
Archaeological Site Visits, Hiking, Small Ship Cruises, Village Visits
Activity Level:
Relaxed
Discover Europe's hidden gem – the Azores Islands on this 14-day Mystique of the Azores Cruise from Bridgetown to Lisbon aboard World Voyager. Explore rugged coastlines, volcanoes, crater lakes, and the UNESCO Global Geopark. Immerse in the pineapple cultivation culture in Ponta Delgada …
Cruise Details
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Explore the California coast
$11,850
EXPLORE

San Francisco, California to New York

24 Day Itinerary aboard Silver Shadow
  • Explore the West Coast
  • Experience Cabo San Lucas
  • Visit Acapulco's sandy beaches
  • Explore Aruba and St. Thomas
Starts / Ends:
San Francisco / New York City
Activities:
Hiking, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
This 24-day San Francisco to New York Cruise aboard Silver Shadow offers delightful sea days and breathtaking sights. Passengers set sail from the golden-gated shores of San Francisco, cruising past iconic West Coast scenery until they reach Los Angeles. During a full day in the star-studded city, …
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-Peopletour 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
$3,390
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
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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 andFábrica de Arte …
Tour Details
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