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Caribbean Trips with Homestays

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On a homestay, you'll get to know Caribbean like someone who lives there instead of just being a tourist. Choose from one of these 4 trips below that feature homestays visiting highlights such as Havana, Cienfuegos, Trinidad, Playa Larga, and Pinar del Río. Combine your homestay with activities like homestays, cultural, land tours, snorkeling, and hiking. Homestay trips to Caribbean start at $2,245 for a 5 to 8 days trip. Please contact one of our Caribbean homestay experts to get started planning your trip!
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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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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
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 and Fábrica de …
Tour Details
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1-4 of 4 Results
TrustScore 4.8 | 375 reviews
TrustScore 4.8 of 5
total score
Based on 375 reviews on
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3 hours ago
Jason has gone above and beyond. We have so much appreciation for him!
Jackie Smedley
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5 hours ago
My travel planner, Jeff, who is on top of his field (based on travel industry awards), is a highly professional, very effective and, at the same time, personally nice individual. What was also critical to me is that he has a first hand experience traveling in the region that I am going to. On top of that, the customer relations director, Sarah, has personally followed up to make sure I'm happy.
alex shaykis
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1 day ago
Very well organiced. Great communication Easy to handle website for required docs to file . Pleasant Experience
Nancy Kaierle
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2 days ago
Very well ececuted. Hily recomended. Great experiance
Nancy Kaierle
review score
4 days ago
Belize adventures I've worked with Adventure Life before in planning trips and appreciate the quality of trips they put together. They use knowledgeable local guides, comfortable lodgings, and assist with transportation. I find trip planning stressful, so am happy to turn it over to them. They work within our parameters of time, budget, activity level, and types of activities to give us great experiences!
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