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Top Greater Antilles Trips & Tours in January 2026

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Discover Greater Antilles in January 2026 on one of these 4 tours hand-selected by the travel experts at Adventure Life. Explore the best of during January 2026 as you enjoy Local Market Visits, Snorkeling, Hiking, Homestays, and Kayaking. Prices for trips in January 2026 range from $3,090 to $31,640 for a vacation of 8 to 12 days. Choose any of the below 4 itineraries in January 2026 and customize it when you contact one of Adventure Life's expert Greater Antilles trip planners.
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Kayaking in Cuba
from $3,390
EXPLORE

Cuba Kayaking West Tour

8 Day Itinerary
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Activities
Kayaking, Homestays
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.
Tour Details
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The crystal blue water of Jost van Dyke
from $3,090
EXPLORE

Jamaica to Antigua

12 Day Itinerary aboard Star Clipper
  • Swim in Montego Bay's waters
  • Explore Santo Domingo
  • Visit the Treasure Island
  • Hike Virgin Gorda trails
Starts / Ends
Port Antonio / St. John's
Activities
Snorkeling, Spa Relaxation
Activity Level
Variable
Explore a paradise of vibrant coral reefs, powder-soft sand, and warm island hospitality on this 12-day cruise from Jamaica to Antigua aboard Star Clipper. Experience crystal-clear water, bright skies, and gentle breezes. Relish in the beauty of untouched beaches and become enchanted by seductive scents and rhythms.
Cruise 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
  • Explore Old San Juan's forts
  • Enjoy salsa music
  • Sail in the British Virgin Islands
  • Explore unique rock formations
Starts / Ends
San Juan / San Juan
Activities
Small Ship Sailing
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.
Cruise Details
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St Barts harbor view
from $8,390
2for1
EXPLORE

Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Barbuda's pink beaches
  • Discover Deshaies’ architecture
  • Visit Gustavia’s charming boutiques
  • Experience Virgin Gorda’s baths
Starts / Ends
St. John's / San Juan
Activities
Local Market Visits, Urban Exploration, Hiking
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.
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