Have questions? We're here.
Relax on the sunny beaches of the Bahamas

Greater Antilles Urban Exploration Tours

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Explore the vibrant urban landscapes of the Greater Antilles on our 3 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.
Filter (3 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Greater Antilles
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, 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.
Tour Details
0
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, Snorkeling
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.
Tour Details
0
Explore the famous rock formations of the baths
from $9,190
2for1
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
Urban Exploration, 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.
Cruise Details
0
1-3 of 3 Results
  • 1

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By

Jeff Rottschafer Adventure Life employee profile
Jeff R
Plan My Trip
We love travel, talk with an expert 1.800.344.6118