Caribbean & Puerto Rico

Destinations / Ports Near You / Caribbean & Puerto Rico

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.

Caribbean & Puerto Rico Cruises

188 cruises cruises

Includes free extras and bonus savings available only from CruiseInsider.

7-night Southern Caribbean Cruise

Roundtrip San Juan

Cruise Line
Celebrity Cruises
Cruise Ship
Summit
Departs
4/6/19
From
$1,129
13-night Eastbound Transatlantic Cruise

San Juan to Malaga

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
4/14/19
From
$2,399
7-night Southern Caribbean Cruise

Roundtrip San Juan

Cruise Line
Celebrity Cruises
Cruise Ship
Summit
Departs
4/20/19
10-night West Indies Explorer Cruise

Roundtrip San Juan

Cruise Line
Viking Cruises
Cruise Ship
Viking Sea (Ocean)
Departs
10/22/19
From
$3,349
25-night Caribbean & South American Shores Cruise

San Juan to Buenos Aires

Cruise Line
Viking Cruises
Cruise Ship
Viking Sun (Ocean)
Departs
10/24/19
 
Call For Pricing
46-night West Indies, Amazon, & South America Cruise

San Juan to Santiago (Valparaiso)

Cruise Line
Viking Cruises
Cruise Ship
Viking Sun (Ocean)
Departs
10/24/19
 
Call For Pricing
7-night Southern Caribbean Cruise

Roundtrip San Juan

Cruise Line
Celebrity Cruises
Cruise Ship
Summit
Departs
10/26/19
10-night West Indies Explorer Cruise

Roundtrip San Juan

Cruise Line
Viking Cruises
Cruise Ship
Viking Sea (Ocean)
Departs
11/1/19
From
$3,349
7-night Southern Caribbean Cruise

Roundtrip San Juan

Cruise Line
Celebrity Cruises
Cruise Ship
Summit
Departs
11/2/19
7-night San Juan and the Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/2/19
From
$1,799
14-night Star Collector – Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/2/19
From
$2,899
7-night Winter Antilles Escape Cruise

San Juan to Bridgetown (Barbados)

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/6/19
From
$1,799
14-night Star Collector: Comprehensive Lesser Antilles Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
11/6/19
From
$3,299
7-night Southern Caribbean Cruise

Roundtrip San Juan

Cruise Line
Celebrity Cruises
Cruise Ship
Summit
Departs
11/9/19
7-night Eastern Caribbean Cruise

San Juan to Marigot

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
11/9/19
From
$2,999
7-night Windward Islands Surf and Sunsets Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/9/19
From
$1,799
14-night Star Collector – Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/9/19
From
$2,899
10-night West Indies Explorer Cruise

Roundtrip San Juan

Cruise Line
Viking Cruises
Cruise Ship
Viking Sea (Ocean)
Departs
11/11/19
From
$3,299
Early Booking Bonus 11-night Caribbean & Central America Cruise

San Juan to Ft. Lauderdale

Cruise Line
Silversea Cruises
Cruise Ship
Silver Whisper
Departs
11/11/19
From
$3,483
Early Booking Bonus 8-night Eastern & Southern Caribbean Cruise

San Juan to Bridgetown (Barbados)

Cruise Line
Silversea Cruises
Cruise Ship
Silver Wind
Departs
11/13/19
From
$2,827
5-night Very Merrytime Eastern Caribbean Cruise

San Juan to Miami

Cruise Line
Disney Cruise Line
Cruise Ship
Disney Magic
Departs
11/15/19
From
$1,150
7-night Southern Caribbean Cruise

Roundtrip San Juan

Cruise Line
Celebrity Cruises
Cruise Ship
Summit
Departs
11/16/19
7-night San Juan and the Virgin Islands Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/16/19
From
$1,799
14-night Star Collector – Lovely Leewards Cruise

Roundtrip San Juan

Cruise Line
Windstar Cruises
Cruise Ship
Star Legend
Departs
11/16/19
From
$2,899
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