Have questions? We're here.
The looming fort walls of San Juan

Greater Antilles Trips in 2022

Travel made your way
Talk with an expert
Customize any aspect of your Caribbean trip. 1.406.541.2677
Help Me Plan My Trip
Filter (10 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Itineraries
  • Destinations
    • Greater Antilles
Sailing in Boston
$5,599
EXPLORE

Boston, MA to Nassau, Bahamas

16 Day Itinerary aboard M/V Victory I
  • Admire Boston's innovation
  • Discover Provincetown
  • Visit Newport
  • Explore Montauk
Starts/ Ends in:
Boston / Nassau
Activities:
Small Ship Cruise, Spa & Relaxing
Activity Level:
Relaxed
Sail on this 16-day itinerary cruising the seaboard from bustling Boston to beachy Nassau aboard M/V Victory I. With stops in Baltimore, Charleston, West Palm Beach, and more, this journey has been handcrafted to sample the Eastern cities of the United States as you head to your final destination …
Cruise Details
0
Cuba homes in Havana
$6,940
EXPLORE

Havana to Cienfuegos

11 Day Itinerary aboard Sea Cloud II
  • Stroll the Malecon in Havana
  • Snorkel and swim at Maria la Gorda
  • Explore beautiful Cienfuegos
Starts/ Ends in:
Havana / Cienfuegos
Activities:
Small Ship Cruise
Activity Level:
Relaxed
Get a glimpse into the history, culture, and lifestyle of modern Cuba with this 11-day cruise from Havana to Cienfuegos aboard Sea Cloud II. Stroll down the famed Malecon promenade in Havana and soak in the distinctive spirit of the city. Snorkel and swim the crystal clear waters of Maria la Gorda, …
Cruise Details
0
Parque Marti in Cienfuegos, Cuba
$6,985
EXPLORE

Havana to Santo Domingo

13 Day Itinerary aboard Sea Cloud II
  • Stroll down the Malecon
  • Snorkel and swim at Maria La Gorda
  • Visit banana farms in Jamaica
  • Marvel at historic Santo Domingo
Starts/ Ends in:
Havana / Santo Domingo
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Board Sea Cloud II for this 13-day cruise from Havana to Santo Domingo. Visit highlights of Cuba, including Cienfuegos, with its colonial architecture; Maria La Gorda, with its clear waters and colorful coral reefs; and, of course, historic Havana, with the famous Malecon promenade. Visit Port …
Cruise Details
0
Kayaking in Cuba
$3,190
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:
Homestay, Kayaking, Land, Snorkeling
Activity Level:
Easy Active
The world’s fascination with Cuba has lasted for many generations, and for good reason. Cuba is a cultural hub, with a mix of descendants of indigenous people, European immigrants, and slaves. The country's music and art draw from these diverse influences. Cuba has also exerted an …
Tour Details
0
Cycling through the revolutionary landscape of Cuba
$3,490
EXPLORE

Cuba Multisport

7 Day Itinerary
  • Bike, kayak, snorkel, and hike Cuba
  • Appreciate Cuba's colonial past
  • Be immersed in Cuba's culture
  • Enjoy excellent wildlife viewing
  • Experience Cuban hospitality
Starts/ Ends in:
Havana / Havana
Activities:
Biking, Hiking, Homestay, Kayaking, Land, Snorkeling, Wildlife Viewing
Activity Level:
Moderate
Experience Cuba by bike, kayak, and on foot on this 7-day guided Cuba multisport tour. This People-to-Peopletour offers myriad opportunities to delve into Cuba's rich traditions, from architecture to lively music and authentic cuisine, and enjoy meaningful exchanges with Cubans. Learn about …
Tour Details
0
Hiker in the Holguin Province, Cuba
$3,490
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
Activities:
Hiking, Homestay, Land, Local Market, Snorkeling, Urban Exploration, Wildlife Viewing
Activity Level:
Moderate
Experience the diversity of Cuba on an 8-day guided Cuba tour. This People-to-People tour explores the diverse urban cities of Cienfuegos, Trinidad, and Havana and provides visitors incredible opportunities to delve into the rich traditions and heritage of Cuban culture. Hike pristine landscapes, …
Tour Details
0
Farmer harvests his crop in Cuba
$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, Homestay, Land, Local Market, Urban Exploration
Activity Level:
Relaxed
Experience Classic Cuba on this 5-day Cars, Rum, and Cigars highlights tour. Encounter Hemingway's Havana as you visit his favorite bars and his former estate. Get a taste of Cuba's revolutionary spirit and contemporary culture with visits to Havana's Tropicana andFábrica de Arte …
Tour Details
0
$4,699
EXPLORE

Southern Coastal Charm

Roundtrip Amelia Island - 12 Day Itinerary aboard M/V Victory I
  • Experience Jacksonville hospitality
  • Visit Amelia Island
  • Explore Brunswick
  • See Beaufort
Starts/ Ends in:
Jacksonville / Amelia Island
Activities:
Small Ship Cruise, Spa & Relaxing
Activity Level:
Relaxed
From the historic South to pristine beaches, a voyage from the Southeast coast to The Bahamas delivers just the right balance of excitement and relaxation. Charleston and Savannah offer a glimpse into coastal Southern living and architecture, while the islands of The Bahamas feature a tropical …
Cruise Details
0
Explore colorful Gustavia
$6,070
EXPLORE

Santo Domingo and Caribbean treasures : Santo Domingo - Fort-de-France

Santo Domingo - Fort-de-France - 13 Day Itinerary aboard Le Champlain
  • Enjoy crystal waters of Caribbean.
  • Explore Santo Domingo.
  • Discover 8 islands on the same time
  • Amaze with landscapes of Guadeloupe
Starts/ Ends in:
Santo Domingo / Fort de France
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
You will board in Santo Domingo, where you will be able to appreciate the charms of the oldest capital of the “New World”, which is a UNESCO World Heritage Site. Located between the Lesser Antilles and the Greater Antilles, the British Virgin Islands are composed of some sixty islands, most …
Cruise Details
0
Enjoy a ride around the islands.
$1,399
EXPLORE

Bahamas Sailing Adventure

7 Day Itinerary aboard Liberty Clipper
  • Explore the Out Islands
  • Learn how to sail and steer
  • Encounter unique wildlife
  • Kayak, snorkel, or paddle board
Activities:
Kayaking, Sailing Schooner, Snorkeling, Stand Up Paddle Board, Wildlife Viewing
Activity Level:
Relaxed
Set sail for new horizons on a barefoot 7-day cruise in the Bahamas. On the 125-foot schooner, the tall ship Liberty Clipper, explore the Out Islands of the Bahamas from this majestic windjammer. Be welcomed aboard by expert crew who are there for your safety and enjoyment. From qualified Captains …
Cruise Details
0
1-10 of 10 Results

Caribbean Travel Guide

Favorite Caribbean Tours & Cruises

Top Greater Antilles Travel Destinations

Greater Antilles Trips by Departure Date

Greater Antilles Trips by Duration

Why Travel With Adventure Life

More Reasons

Recognized By

All News