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.
498 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
10/19/25
|
From
$674
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
10/19/25
|
From
$2,064
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
10/19/25
|
From
$1,118
|
|
7-night Halloween On The High Seas Southern Caribbean Cruise From San Juan
Roundtrip San Juan |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
10/24/25
|
From
$1,547
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
10/26/25
|
From
$698
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
10/26/25
|
From
$2,030
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
10/26/25
|
From
$1,134
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
10/26/25
|
From
$2,662
|
|
7-night Halloween On The High Seas Southern Caribbean Cruise From San Juan
Roundtrip San Juan |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
10/31/25
|
From
$1,673
|
|
6-night Western Caribbean Cruise
San Juan to Tampa |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
11/2/25
|
From
$723
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
11/2/25
|
From
$1,094
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
11/2/25
|
From
$2,000
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/2/25
|
From
$2,862
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/2/25
|
From
$4,693
|
|
7-night Southern Caribbean Cruise From San Juan
Roundtrip San Juan |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
11/7/25
|
From
$1,638
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
11/8/25
|
From
$823
|
|
7-night Southern Caribbean Voyage
San Juan to Bridgetown (Barbados) |
Cruise Line
Azamara Cruises
|
Cruise Ship
Azamara Quest
|
Departs
11/8/25
|
From
$1,799
|
|
14-night Eastern Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Azamara Cruises
|
Cruise Ship
Azamara Quest
|
Departs
11/8/25
|
From
$3,299
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
11/9/25
|
From
$976
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
11/9/25
|
From
$1,084
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
11/9/25
|
From
$1,984
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/9/25
|
From
$2,630
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/9/25
|
From
$4,193
|
|
5-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Evrima
|
Departs
11/13/25
|
Call For Pricing
|