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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, Playa Larga, Topes de Collantes, and Trinidad. Combine your homestay with activities like Hiking, Snorkeling, Kayaking, Local Market Visits, and Urban Exploration. 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
from $3,590
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Cuba Kayaking West Tour

8 Day Itinerary
Activity Level
Easy Active
Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Tour Details
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Cycling through the revolutionary landscape of Cuba
from $3,890
EXPLORE

Cuba Multisport

8 Day Itinerary
Starts / Ends
Havana / Havana
Activities
Kayaking, Biking
Activity Level
Moderate
Explore the intriguing island of Cuba on this active 8-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil countryside. Experience great colonial cities including Havana, Cienfuegos, Trinidad, and Sancti Spiritus. Discover Cuba's history, rich traditions, and dynamic present on this Cuba multisport trip.
  • Bike, kayak, snorkel, and hike Cuba
  • Appreciate Cuba's colonial past
  • Be immersed in Cuba's culture
  • Enjoy excellent wildlife viewing
  • Experience Cuban hospitality
Tour Details
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Havana Musicians
from $2,245
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Classic Cuba

Cars, Rum, and Cigars - 5 Day Itinerary
Activities
Homestays, Hiking, Urban Exploration, Local Market Visits
Activity Level
Relaxed
Rolled cigars, rum spiked with sugarcane juice, and colorful vintage cars - these are the icons of Cuba that await you on this 5-day People-to-People classic Cuba tour. Find yourself immersed in legendary Cuban culture as you explore legendary Havana, the tobacco mecca Vuelta Abajo, and breathtaking Valle de Viñales.
  • 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
Tour Details
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Farmer harvests his crop in Cuba
from $3,590
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Cuba Walking Tour

8 Day Itinerary
Starts / Ends
Havana / Havana
Activities
Snorkeling, Wildlife Viewing
Activity Level
Moderate
Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, Vinales, Havana, and five parks & reserves. Explore by foot and encounter local experts, farmers, and artists as you gain insight into their history, traditions & vibrant culture on this highlights Cuba trip.
  • 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
Tour Details
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TrustScore 4.8 | 545 reviews
TrustScore 4.8 of 5
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Based on 545 reviews on
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1 month ago
Jess is funtastic! She listens and fines the adventure I want to share with my granddaughter
carolynn basque

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