Have questions? We're here.
Bright blue waters of the Caribbean sea

Trips to Local Caribbean Markets

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Filter (29 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Caribbean
Relax on the pristine beaches of the Virgin Islands
from $11,600
EXPLORE

Bridgetown to Bridgetown

22 Day Itinerary aboard Silver Spirit
  • Explore top Caribbean islands
  • Visit Bequia and Iles des Saintes
  • Explore Gustavia’s historic harbor
  • Experience the Caribbean culture
Starts / Ends
Bridgetown / Bridgetown
Activities
Wildlife Viewing, Spa Relaxation
Activity Level
Variable
Sail round-trip from Bridgetown aboard Silver Spirit on a 22-day Caribbean cruise. Explore top islands like St. Lucia, Martinique, and Barbados, plus hidden gems like Bequia and Iles des Saintes. Enjoy beach days, island tours, and cultural stops with long port calls.
Cruise Details
0
St. George's, Grenada's charming capital city known for having the most beautiful harbor in the Caribbean.
from $3,090
EXPLORE

Grenada to Grenada

Roundtrip St George - 12 Day Itinerary aboard Star Clipper
  • Explore St. George’s Fort George
  • Discover Charlotteville’s Tobago
  • Unwind on Carriacou beach
  • Visit Martinique ruins
Starts / Ends
St. Georges / St. Georges
Activity Level
Variable
Set sail on a 12-day cruise aboard the Star Clipper, exploring stunning islands like Tobago and Martinique, with highlights including the Tobago Cays and St. Lucia's waterfalls. Experience the Caribbean's serene beauty and rich culture while enjoying activities like snorkeling and history.
Cruise Details
0
Cayo Arena Island
from $3,793
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
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
Sunset view by the cliff houses
from $3,400
EXPLORE

Dominican Republic: North Coast Expedition

8 Day Itinerary
  • Enjoy canyoning in Puerto Plata
  • See the landscape using 4x4 buggy
  • Visit the Los Pepines murals.
  • Learn about tobacco production
  • See the lovely bay of Rio San Juan
  • Zip line over the Laguna Dudu
Starts / Ends
Puerto Plata / Puerto Plata
Activities
Ziplining, Hiking
Activity Level
Easy Active
Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day Dominican Republic trip, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.
Tour Details
0
Enjoy the beautiful blue Caribbean
from $8,050
EXPLORE

Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper
  • Explore St. George’s panoramic view
  • Discover Charlotteville coastline
  • Unwind at Englishman’s Bay
  • Visit Martinique ruins
Starts / Ends
St. Georges / St. Georges
Activities
Village Visits
Activity Level
Variable
Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.
Cruise Details
0
The vivid colors of the San Blas Islands
from $4,330
EXPLORE

Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper
  • Explore Bridgetown’s heritage
  • Discover St. George’s coastal views
  • Admire Kralendijk’s marine life
  • Wander Willemstad’s streets
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.
Cruise Details
0
Stroll along the beautiful beaches of the Caribbean
from $3,420
EXPLORE

Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - 21 Day Itinerary aboard Star Flyer
  • Explore Philipsburg’s Dutch side
  • Experience Marigot’s markets
  • Unwind while crossing the Atlantic
  • Visit Ponta Delgada’s churches
Starts / Ends
Philipsburg / Malaga
Activity Level
Variable
Set sail on a 21-day cruise aboard the Star Flyer, starting in Philipsburg and visiting Ponta Delgada in the Azores. End your journey in Malaga, Spain, exploring its Moorish heritage while enjoying 18 days at sea.
Cruise Details
0
Panama's turquoise waters
from $4,450
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Explore Balboa’s colonial charm
  • Transit Panama’s iconic canal
  • Discover San Blas culture
  • Enjoy Aruba’s clear waters
Starts / Ends
Balboa / St. John's
Activity Level
Variable
Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.
Cruise Details
0
Deans Blue Hole
from $5,175
EXPLORE

West Caribbean Cruise

Belize - Fort Lauderdale - 10 Day Itinerary aboard SH Vega
  • Explore Belize City
  • Sail toward Grand Cayman
  • Swim with stingrays
  • Discover Montego Bay
Starts / Ends
Belize City / Fort Lauderdale
Activities
Rainforest Exploration, Helicopter Tours
Activity Level
Variable
Embark on an 10-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
Take a leisurely stroll through beautiful Bridgetown
from $5,610
EXPLORE

Eastbound Atlantic Ocean Crossing

Barbados to France - 29 Day Itinerary aboard Royal Clipper
  • See Ponta Delgada, Azores scenery
  • See Malaga, Spain's architecture
  • Visit Mallorca’s Gothic cathedral
  • Visit Calvi’s coastal citadel
Starts / Ends
Bridgetown / Nice
Activity Level
Variable
Set sail on a 29-day Eastbound Atlantic Ocean cruise aboard Royal Clipper. Enjoy sailing, historic ports, and scenic coastal landscapes.
Cruise Details
0
Balboa
from $3,150
EXPLORE

Panama to Aruba

12 Day Itinerary aboard Star Clipper
  • Transit the Panama Canal locks
  • Walk colonial Balboa streets
  • Explore forts in Portobelo
  • Visit San Blas and Guna villages
  • See Cartagena and Santa Marta
Starts / Ends
Balboa / Oranjestad
Activities
Archaeological Site Visits, Small Ship Sailing, Local Market Visits, Snorkeling
Activity Level
Variable
Sail the Panama Canal on a 10-day Star Clippers cruise through Central America. Begin in Balboa, then transit the Panama Canal and see the locks in action. Explore Spanish forts in Portobelo, meet the Guna people in the San Blas Islands, and discover Colombia’s coastal cities of Cartagena and Santa Marta. Enjoy scenic days under sail.
Cruise Details
0
19-29 of 29 Results

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