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
Brilliance of the Seas
|
Departs
11/30/25
|
From
$683
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
11/30/25
|
From
$2,024
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/30/25
|
From
$2,662
|
|
13-night Star Collector: Beaches & Bastions Of The BVI And Spanish Caribbean Cruise
San Juan to Colon (Panama) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/30/25
|
From
$4,098
|
|
20-night Star Collector: Central America & The Caribbean: Cloudforest Coastlines, Canal Locks & Calypso Concerts Cruise
San Juan to Puerto Caldera (Puntarenas) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/30/25
|
Call For Pricing
|
|
20-night Southern Caribbean Discovery Cruise
San Juan to Barbados (Bridgetown) |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$9,459
|
|
12-night Treasures Of Aruba, Bonaire & Curacao Cruise
Roundtrip San Juan |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$6,114
|
|
7-night A Journey into the Caribbean’s Most Desirable Shores
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
12/5/25
|
From
$3,280
|
|
16-night An Extended Journey Of Bewitching Caribbean Gems
San Juan to Bridgetown (Barbados) |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
12/5/25
|
From
$6,550
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
12/6/25
|
From
$752
|
|
7-night Southern Caribbean Voyage
San Juan to Bridgetown (Barbados) |
Cruise Line
Azamara Cruises
|
Cruise Ship
Azamara Quest
|
Departs
12/6/25
|
From
$1,419
|
|
13-night Eastern Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Azamara Cruises
|
Cruise Ship
Azamara Quest
|
Departs
12/6/25
|
From
$2,609
|
|
4-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Evrima
|
Departs
12/6/25
|
Call For Pricing
|
|
7-night Leeward Islands Adventure Cruise
Roundtrip San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/7/25
|
From
$5,419
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
12/7/25
|
From
$841
|
|
7-night Caribbean Cruise: Barbados, Antigua & St. Lucia
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
12/7/25
|
From
$1,081
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
12/7/25
|
From
$2,124
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
12/7/25
|
From
$1,158
|
|
6-night The Spanish Main: Rise Of The New World Cruise
San Juan to Colon (Panama) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/7/25
|
From
$2,535
|
|
13-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise
San Juan to Puerto Caldera (Puntarenas) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/7/25
|
From
$4,293
|
|
3-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Ilma
|
Departs
12/9/25
|
Call For Pricing
|
|
5-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Evrima
|
Departs
12/10/25
|
Call For Pricing
|
|
6-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Ilma
|
Departs
12/12/25
|
Call For Pricing
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
12/13/25
|
From
$748
|