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Top Greater Antilles Tours & Cruises in 2025

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Discover the best the world has to offer with Adventure Life’s expert-curated Greater Antilles tours 2025. From San Juan, Santo Domingo, Culebra, and Vieques to hidden gems off the beaten path, our 5 top-rated itineraries take you deep into Greater Antilles’s breathtaking landscapes. Guided by bilingual experts, these immersive experiences cater to adventurers seeking unique journeys in small groups or customizable private tours.

Choose from a variety of 8 days itineraries starting at $2,613 to $31,240. You’ll find options that suit your travel style. Whether you’re passionate about Village Visits, Local Market Visits, Small Ship Sailing, Archaeological Site Visits, and Hacienda Visits or eager to explore Greater Antilles’s rich culture and natural beauty, our Greater Antilles tours 2025 deliver unforgettable moments. Each itinerary blends awe-inspiring exploration with a commitment to sustainability to ensure your adventure supports the preservation of our planet.

Adventure Life’s dedication to personalized travel promises your Greater Antilles tour 2025 is seamless from start to finish. From arranging transportation to selecting accommodations tailored to your preferences, we’ll take care of every detail. Our expert recommendations and insider tips make your journey even more enriching.

Contact our specialists today to start planning your Greater Antilles tour 2025. Whether you’re a solo traveler, a couple, or part of a group, Adventure Life will create a transformative experience you’ll treasure forever.
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    • Greater Antilles
Cayo Arena Island
from $3,125
EXPLORE

Dominican Republic: Culture and Cocktails

8 Day Itinerary
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Archaeological Site Visits
Activity Level
Easy Active
This 8-day journey will give you a genuine taste of the Dominican Republic. From UNESCO World Heritage Sites to street art and local delicacies, immerse yourself in the diverse landscapes and cultures of this Caribbean gem. With optional beach extensions, savor every moment of your unforgettable journey.
  • Visit UNESCO site in Santo Domingo
  • Visit coffee factory in Jarabacoa
  • Visit Los Pepines murals
  • Swim in azure waters of Cayo Arena
  • Visit cocoa & chocolate plantation
Tour Details
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Explore the famous rock formations of the baths
from $5,245
EXPLORE

A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
Starts / Ends
San Juan / San Juan
Activity Level
Variable
Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and salsa-filled cafes. Discover UNESCO-listed sites like La Fortaleza and Fort San Felipe del Morro, resonating with centuries of history and cultural vibrancy.
  • Explore Old San Juan's forts
  • Enjoy salsa music
  • Sail in the British Virgin Islands
  • Explore unique rock formations
Cruise Details
0
Explore beautiful Jost van Dyke
from $10,590
2for1
EXPLORE

Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
San Juan / St. John's
Activities
Local Market Visits, Hiking
Activity Level
Variable
Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.
  • Discover Culebra Island’s shores
  • Explore Vieques Island waterfront
  • Tour St. John’s Annaberg ruins
  • Relax on Jost Van Dyke’s White Bay
Cruise Details
0
Areal view of Old city of Santo Domingo
from $2,612
EXPLORE

Best of Dominican Republic

8 Day Itinerary
Starts / Ends
Punta Cana / Punta Cana
Activities
Hacienda Visits, Volunteering
Activity Level
Relaxed
Discover the best of the Dominican Republic's highlights on this 8-day adventure, from the idyllic beaches of Punta Cana to the historic charm of Santo Domingo, the lush landscapes of Jarabacoa, the cultural richness of Santiago de los Caballeros, the bustling streets of San Francisco de Macoris, and the coastal allure of Las Terrenas.
  • Visit UNESCO site in Santo Domingo
  • Taste the culture and local food
  • Visit coffee factory in Jarabacoa
  • Learn about tobacco production
  • Visit cocoa & chocolate plantation
  • See the beaches of Las Terrenas
Tour Details
0
St Barts harbor view
from $7,990
2for1
EXPLORE

Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
St. John's / San Juan
Activities
Village Visits, Small Ship Sailing, Wildlife Viewing
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
  • Explore Barbuda's pink beaches
  • Discover Deshaies’ architecture
  • Visit Gustavia’s charming boutiques
  • Experience Virgin Gorda’s baths
Cruise Details
0
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