Have questions? We're here.
Relax on the sunny beaches of the Bahamas
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Filter (7 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Greater Antilles
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
0
Cayo Arena Island
from $3,125
EXPLORE

Dominican Republic: Culture and Cocktails

8 Day Itinerary
  • 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
Starts / Ends
Santo Domingo / Santo Domingo
Activities
Village 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.
Tour Details
0
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
Homestays
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
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
Areal view of Old city of Santo Domingo
from $2,612
EXPLORE

Best of Dominican Republic

8 Day Itinerary
  • 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
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.
Tour Details
0
Explore the famous rock formations of the baths
from $7,990
2-for-1
EXPLORE

Quintessential Caribbean

8 Day Itinerary aboard Emerald Sakara
  • Relax on Prickly Pear Cays' beaches
  • Visit Guadeloupe’s fishing village
  • Visit port of Falmouth Harbour
  • Wander through lively Cruz Bay
Starts / Ends
San Juan / St. Thomas
Activities
Archaeological Site Visits
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbour, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays. Enjoy unique experiences and stunning landscapes throughout your cruise.
Cruise Details
0
St Barts harbor view
from $7,990
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
Hiking, Urban Exploration, Local Market Visits
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
1-7 of 7 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