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Greater Antilles Bicycling Tours & Trips

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On these top 5 Greater Antilles bicycling tours, you'll stroll down meandering roads, trails, and bike paths as you take in the Greater Antilles scenery.  A guided small group or private guided cycling tour of Greater Antilles may include bike rides near popular cycling destinations like Santo Domingo, Havana, Cienfuegos, Las Terrazas, and Pinar del Río. Our Greater Antilles bicycling trips start at $2,660 for a 8 days tour and may include leisure cruising, mountain biking, or road biking. Tell us about your ideal Greater Antilles cycling adventure and one of our Greater Antilles travel experts will help you build the ideal bicycling vacation.
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Cycling through the revolutionary landscape of Cuba
from $3,890
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
Kayaking, Homestays, Wildlife Viewing
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.
Tour Details
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Bicycle on Cuban street
from $4,390
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
Activity Level
Moderate
A cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where the island's rich history isn't just remembered—it is lived every day. It reveals Cuba’s greatest resource and truest legend: its people.
Tour Details
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Rocky banks and flowing waters of the Jimenoa River
from $7,134
EXPLORE

Dominican Republic Explorer in Depth

15 Day Itinerary
  • Cayo Arena snorkeling
  • Santo Domingo city tour
  • Explore Los Haitises National Park
  • Relax at Las Galeras beaches
  • Choose your adventure in Jarabacoa
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Snorkeling, Village Visits
Activity Level
Relaxed
Travel with a private driver-guide across the Dominican Republic for 15 days of nature, history, and coastal relaxation. Explore the colonial center of Santo Domingo before heading inland to the mountains of Jarabacoa. Discover hidden beaches, snorkel vibrant coral reefs, and rest each night in comfortable eco-lodges and boutique hotels.
Tour Details
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Tropical Dominican Republic beach with palm trees
from $2,660
EXPLORE

Dominican Republic North Coast Beaches

Self Drive Tour - 15 Day Itinerary
  • Cayo Arena snorkeling
  • Santo Domingo history tour
  • 27 Waterfalls canyoning
  • Cabarete beach kayaking and surfing
  • Samana Peninsula beaches
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Ziplining
Activity Level
Easy Active
Spend 15 days driving the Dominican Republic's north coast, from the colonial streets of Santo Domingo to the fishing village of Punta Rucia, the surfer town of Cabarete, and the beaches of Las Terrenas on the Samana Peninsula. This self-drive tour combines a guided city tour, snorkeling, and open coastal roads with free time at each stop.
Tour Details
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Ziplining through the mountains
from $3,564
EXPLORE

Dominican Republic Active Island Experience

Self Drive Tour - 15 Day Itinerary
  • Tour the historical Colonial Zone
  • Drive through the mountainous
  • Hike to a towering waterfall
  • Choose your adventure
  • Hike to seven secluded beaches and
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Hiking, Biking, Archaeological Site Visits
Activity Level
Moderate
This 15-day self-drive tour crosses the Dominican Republic from Santo Domingo's Colonial Zone to the cool highlands of Jarabacoa, the surf town of Cabarete, and the beaches of the Samaná Peninsula. Along the way, you raft rivers, hike to waterfalls, bike through history, and explore secluded coves reachable only by boat.
Tour Details
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Kassandra Magruder Adventure Life employee profile
Kassandra M.
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