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

Greater Antilles Tours & Cruises in 2026

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
Experience the stunning beauty and rich culture of the Greater Antilles on our 6 diverse tours & cruises for 2026. Explore the vibrant destinations of the Caribbean, from the lush landscapes of Cuba to the historical sites of the Dominican Republic and the picturesque beaches of Puerto Rico. Immerse yourself in the local flavors and rhythms of the region, with opportunities for cultural experiences, wildlife viewing, and beach relaxation over 8 to 12 days. Discover the colorful streets of Havana, taste the flavorsome cuisine of the islands, and soak up the warm hospitality of the Caribbean people. With tours starting at $3,090 to $31,640, there's no better time to embark on a journey that will leave you with unforgettable memories of the Greater Antilles. To start planning your dream Caribbean adventure, contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (6 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Greater Antilles
Nassau Lighthouse
from $7,590
2-for-1
EXPLORE

Caribbean Escapade

8 Day Itinerary aboard Emerald Sakara
  • Explore the pristine beaches
  • Snorkel in crystal-clear waters
  • Relax on secluded Gordon’s Beach
  • Explore Grand Turk’s beaches
Starts / Ends
San Juan / Miami
Activities
Kayaking
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites. Enjoy the white sands of Emerald Bay in The Bahamas and visit Nassau's vibrant cityscape and historic sites.
Cruise Details
0
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
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
0
Deans Blue Hole
from $4,380
EXPLORE

West Caribbean Cruise

Belize - Fort Lauderdale - 11 Day Itinerary aboard SH Vega
  • Witness Bahama's pinkest flamingo
  • Swim with nurse sharks in Exuma
  • Snorkel vibrant coral reefs
  • Visit Cockscomb wildlife sanctuary
Starts / Ends
Belize City / Fort Lauderdale
Activities
Snorkeling, Wildlife Viewing, Rainforest Exploration
Activity Level
Variable
Embark on an 11-day SH Vega cruise through the Western Caribbean. Explore Mayan ruins in Belize, relax on Grand Cayman's beaches, snorkel Montego Bay’s reefs, and visit Jamaica’s mountains. Enjoy birdwatching at Great Inagua, swim with sharks in the Exumas, and marvel at Nassau’s beauty.
Cruise Details
0
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
0
Explore beautiful Jost van Dyke
from $7,740
2-for-1
EXPLORE

Caribbean Yachting Hideaways

St Thomas - St John's - 8 Day Itinerary aboard Emerald Azzurra
  • Visit The Baths’ granite formation
  • Explore Culebra's white-sand beach
  • Experience swimming off the yacht
  • Discover the history of St. John
Starts / Ends
St. Thomas / Antigua
Activities
Adventure Options
Activity Level
Variable
Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz Bay’s scenic hikes, and Virgin Gorda’s famous Baths. Discover Philipsburg’s vibrant culture, Gustavia’s idyllic beaches, and Montserrat’s volcanic history.
Cruise Details
0
St Barts harbor view
from $8,390
2-for-1
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, Hiking, Urban Exploration
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.
Cruise Details
0
1-6 of 6 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

Tilly Pearson employee headshot
Tilly P
Plan My Trip
We love travel, talk with an expert 1.800.344.6118