Caribbean

The Caribbean has been a haven for seafarers for centuries and is now considered heaven for modern-day travelers. With hundreds of unique islands and thousands of miles of unspoiled beaches dotted with secret bays, hidden coves and incredible ports of call, the Caribbean is widely considered among the world’s best vacation destinations.

Whether you enjoy the hustle and bustle of busy island ports, the sanctitude and solitude of hidden beaches, or fishing, diving and other aquatic adventures, there is something for every age and activity level in the breathtaking Caribbean islands of the Bahamas, Barbados, Virgin Islands, Cuba, Jamaica, Martinique, Puerto Rico, Trinidad and Tobago, Turks and Caicos, West Indies and more.

There are dozens of Caribbean cruise options to choose from, so speak to a Cruise Insider today at 1 (877) 734-6858 to start planning your island adventure or choose from one of the many Caribbean voyages offered below.

Caribbean Cruises Top
Cruises marked with are part of our Insider Advantage program which include free extras only available at CruiseInsider.
  Itinerary Cruise Line Ship Departing Extras Price
7-night Timeless Cuba Voyage Oceania Cruises
Sirena
Sirena 10/3/18
Roundtrip Miami
From $1,899
5-night Halloween on the High Seas – Bermuda Cruise Disney Cruise Line
Disney Magic
Disney Magic 10/4/18
Roundtrip New York City
  From $1,220
3-night Bahamas Cruise Norwegian Cruise Line
Norwegian Sky
Norwegian Sky 10/5/18
Roundtrip Miami
  From $279
3-night Halloween on the High Seas Bahamian Cruise Disney Cruise Line
Disney Dream
Disney Dream 10/5/18
Roundtrip Port Canaveral
  From $1,338
7-night Halloween on the High Seas – Eastern Caribbean Cruise Disney Cruise Line
Disney Fantasy
Disney Fantasy 10/6/18
Roundtrip Port Canaveral
  From $1,638
7-night Western Caribbean Cruise Norwegian Cruise Line
Norwegian Getaway
Norwegian Getaway 10/7/18
Roundtrip Miami
  From $319
7-night Cuba and Caribbean Cruise Norwegian Cruise Line
Norwegian Sun
Norwegian Sun 10/7/18
Roundtrip Miami
  From $259
18-night Pacific Treasures Voyage Oceania Cruises
Regatta
Regatta 10/8/18
San Francisco to Miami
  From $4,749
4-night Cuba and Bahamas Cruise Norwegian Cruise Line
Norwegian Sky
Norwegian Sky 10/8/18
Roundtrip Miami
  From $169
20-night Caribbean and Panama Canal Explorer Cruise Princess Cruises
Caribbean Princess
Caribbean Princess 10/8/18
Roundtrip Ft. Lauderdale
  Call For Pricing
10-night Iconic Lighthouses & Pink Sands Cruise Regent Seven Seas Cruises
Seven Seas Navigator
Seven Seas Navigator 10/8/18
Roundtrip New York City
From $5,349
10-night Iconic Lighthouses & Pink Sands Cruise Regent Seven Seas Cruises
Seven Seas Navigator
Seven Seas Navigator 10/8/18
Roundtrip New York City
Call For Pricing
4-night Halloween on the High Seas Bahamas Cruise Disney Cruise Line
Disney Dream
Disney Dream 10/8/18
Roundtrip Port Canaveral
  From $1,104
34-night Canada/New England, Bermuda, and Eastern Seaboard Cruise Regent Seven Seas Cruises
Seven Seas Navigator
Seven Seas Navigator 10/8/18
New York City to Miami
  Call For Pricing
9-night Breezes, Bays & Beaches Voyage Oceania Cruises
Sirena
Sirena 10/10/18
Roundtrip Miami
  From $1,999
22-night Panama to Paradise Cruise Regent Seven Seas Cruises
Seven Seas Mariner
Seven Seas Mariner 10/10/18
Miami to Oahu
  From $9,999
22-night Panama to Paradise Cruise Regent Seven Seas Cruises
Seven Seas Mariner
Seven Seas Mariner 10/10/18
Miami to Oahu
Call For Pricing
66-night Grand Pacific Paradise Cruise Regent Seven Seas Cruises
Seven Seas Mariner
Seven Seas Mariner 10/10/18
Miami to Sydney
  From $31,999
10-night Panama Canal with Costa Rica and Caribbean Cruise Princess Cruises
Island Princess
Island Princess 10/11/18
Roundtrip Ft. Lauderdale
  From $1,365
23-night Star Collector: Eastern Seaboard Grand Tour Cruise Windstar Cruises
Star Pride
Star Pride 10/11/18
Montreal to San Juan
Call For Pricing
3-night Bahamas Cruise Norwegian Cruise Line
Norwegian Sky
Norwegian Sky 10/12/18
Roundtrip Miami
  From $249
3-night Halloween on the High Seas Bahamian Cruise Disney Cruise Line
Disney Dream
Disney Dream 10/12/18
Roundtrip Port Canaveral
  From $969
14-night Transatlantic Cruise SeaDream Yacht Club
SeaDream II
SeaDream II 10/13/18
Malaga to San Juan
From $3,799
6-night Halloween on the High Seas – Bermuda Cruise Disney Cruise Line
Disney Magic
Disney Magic 10/13/18
Roundtrip New York City
  From $1,104

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