Caribbean & Puerto Rico

Caribbean & Puerto Rico Cruises

Every island in the Caribbean is incredibly unique, but all are indescribably beautiful. This collection of 700 islands truly has it all; movie-set beauty, coconut-tree-clad mountains, verdant valleys of sugar-cane and bananas, blazingly blue waters and seashores galore. From the the gourmet dining, glitzy nightlife and glorious culture of Puerto Rico to the pristine beaches, exotic natural wonders and unique, enchanting people you’ll meet on every Caribbean island, any cruise leaving from the West Indies means you’ll already be in a vacation state-of-mind before you ever step onboard.

Departure ports include: San Juan (Puerto Rico), Barbados, U.S. Virgin Islands
Caribbean & Puerto Rico 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
10-night Southern Caribbean Cruise Norwegian Cruise Line
Norwegian Dawn
Norwegian Dawn 2/7/19
Roundtrip San Juan
  From $2,449
10-night South America and the Caribbean Cruise Viking Cruises
Viking Sea (Ocean)
Viking Sea (Ocean) 2/7/19
Roundtrip San Juan
  Call For Pricing
7-night Caribbean & Central America Cruise Silversea Cruises
Silver Spirit
Silver Spirit 2/8/19
Roundtrip San Juan
From $3,500
7-night Cuba Cruise Silversea Cruises
Silver Wind
Silver Wind 2/14/19
San Juan to Ft. Lauderdale
Call For Pricing
7-night Caribbean & Central America Cruise Silversea Cruises
Silver Spirit
Silver Spirit 2/15/19
Roundtrip San Juan
From $3,500
7-night Caribbean Cruise SeaDream Yacht Club
SeaDream I
SeaDream I 2/16/19
San Juan St. Thomas
From $3,499
7-night Winter Antilles Escape Cruise Windstar Cruises
Star Pride
Star Pride 2/16/19
San Juan to Bridgetown
  From $1,799
14-night Star Collector: Comprehensive Lesser Antilles Cruise Windstar Cruises
Star Pride
Star Pride 2/16/19
Roundtrip San Juan
  Call For Pricing
7-night Southern Caribbean Cruise Norwegian Cruise Line
Norwegian Dawn
Norwegian Dawn 2/17/19
Roundtrip San Juan
  From $549
10-night West Indies Explorer Cruise Viking Cruises
Viking Sea (Ocean)
Viking Sea (Ocean) 2/17/19
Roundtrip San Juan
  Call For Pricing
10-night Caribbean Cruise Silversea Cruises
Silver Spirit
Silver Spirit 2/22/19
San Juan to Ft. Lauderdale
From $4,900
7-night Southern Caribbean B Cruise Norwegian Cruise Line
Norwegian Dawn
Norwegian Dawn 2/24/19
Roundtrip San Juan
From $579
10-night West Indies Explorer Cruise Viking Cruises
Viking Sea (Ocean)
Viking Sea (Ocean) 2/27/19
Roundtrip San Juan
  Call For Pricing
7-night San Juan & the Virgin Islands Cruise Windstar Cruises
Star Pride
Star Pride 3/2/19
Roundtrip San Juan
  From $1,699
7-night Southern Caribbean Cruise Norwegian Cruise Line
Norwegian Dawn
Norwegian Dawn 3/3/19
Roundtrip San Juan
  From $499
7-night Eastern & Southern Caribbean Cruise Silversea Cruises
Silver Wind
Silver Wind 3/3/19
San Juan to Bridgetown
From $3,900
10-night West Indies Explorer Cruise Viking Cruises
Viking Sea (Ocean)
Viking Sea (Ocean) 3/9/19
Roundtrip San Juan
  Call For Pricing
7-night Caribbean Cruise SeaDream Yacht Club
SeaDream I
SeaDream I 3/9/19
Roundtrip San Juan
From $3,399
10-night Gems of the Leeward Islands Cruise Windstar Cruises
Star Pride
Star Pride 3/9/19
Roundtrip San Juan
  From $1,799
23-night Star Collector: Caribbean Sands & Portuguese Castles Cruise Windstar Cruises
Star Pride
Star Pride 3/9/19
San Juan to Lisbon
  From $2,799
7-night Southern Caribbean B Cruise Norwegian Cruise Line
Norwegian Dawn
Norwegian Dawn 3/10/19
Roundtrip San Juan
  From $499
7-night Caribbean & Central America Cruise Silversea Cruises
Silver Spirit
Silver Spirit 3/15/19
San Juan to Bridgetown (Barbados)
From $3,300
7-night Caribbean Cruise SeaDream Yacht Club
SeaDream I
SeaDream I 3/16/19
Roundtrip San Juan
From $3,599
7-night Southern Caribbean Cruise Norwegian Cruise Line
Norwegian Dawn
Norwegian Dawn 3/17/19
Roundtrip San Juan
  From $529

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