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Greater Antilles Urban Exploration Tours

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Explore the vibrant urban landscapes of the Greater Antilles on our 4 captivating city tours for 2026. Embrace the lively Caribbean spirit as you uncover hidden gems in San Juan, St. John's, and beyond. From the active reefs of Culebra to the charming streets of Cruz Bay, each stop offers a unique blend of urban exploration and cultural immersion. Delight in the French flair of Gustavia, the tranquility of Friars Beach, and the charm of Vieques Island. With activities like village visits, wildlife viewing, and snorkeling, these tours cater to every adventurer. Join us on a journey that promises relaxation, discovery, and unforgettable memories. To start planning your Caribbean city adventure, contact one of Adventure Life's tour specialists for help crafting your dream itinerary.
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Havana Musicians
from $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
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.
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Stroll along the beaches of Puerto Rico
from $9,295
EXPLORE

Paradise Beaches from the U.S. Virgin Islands to The Bahamas

San Juan - Miami - 10 Day Itinerary aboard Emerald Kaia
  • Tour Grand Turk lighthouse
  • Wander Gordon's Beach
  • Walk Nassau bustling Straw Market
  • Dive San Salvador Island
Starts / Ends
San Juan / Miami
Activities
Urban Exploration, Local Market Visits, Snorkeling, Archaeological Site Visits
Activity Level
Variable
Set sail on a 10-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring the beautiful Turks and Caicos Islands and vibrant marine life in The Bahamas. Enjoy fresh local seafood and conclude your journey in the lively metropolis of Miami, blending cultural discovery with natural beauty.
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Farmer harvests his crop in Cuba
from $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
Starts / Ends
Havana / Havana
Activities
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.
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Explore the famous rock formations of the baths
from $9,190
EXPLORE

Splendours of the Caribbean

San Juan - St. Thomas - 7 Day Itinerary aboard Emerald Sakara
  • Tour Nelson’s Dockyard
  • Explore Nevis Island plantations
  • Walk through Gustavia
  • Swim Prickly Pear Cays
Starts / Ends
San Juan / St. Thomas
Activities
Village Visits
Activity Level
Variable
Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.
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TrustScore 4.9 | 998 reviews
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8 months ago
Mary is always a pleasure to work with. She is knowledgeable, prompt and gives good pros and cons for any choices we had to make.
MTPhil
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1 year ago
Jess is funtastic! She listens and fines the adventure I want to share with my granddaughter
carolynn basque
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1 year ago
Angie was great! Always kept us informed of our trip. Great personality and easy to work with! Jean Hershey
jean hershey
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2 years ago
I love working with Adventure Life. They have come through with every trip. Activities, excursions, stays, food are all top notch. Agents are knowledgeable, efficient and helpful.
Deb Jewell
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2 years ago
I received a quick and friendly response from my contact, Christina Mayo, both in email and phone calls. My request for information was provided in less than a day. She took a few minutes to chat about family and events. Dealing with her has always been a pleasure!
Mary Ann

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