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.
237 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
7-Night Spanish & British Caribbean Delight Cruise
San Juan to St. Maarten (Philipsburg) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
12/13/25
|
From
$3,999
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
12/13/25
|
From
$678
|
|
7-Night Grand Island Adventure Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/14/25
|
From
$3,999
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
12/14/25
|
From
$697
|
|
7-night Southern Caribbean Cruise
|
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
12/14/25
|
From
$1,198
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
12/19/25
|
From
$3,599
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
12/20/25
|
From
$872
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
12/21/25
|
From
$1,129
|
|
7-night Southern Caribbean Holiday Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
12/21/25
|
From
$969
|
|
7-Night Tropical New Year's Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
12/27/25
|
Call For Pricing
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
12/27/25
|
From
$872
|
|
7-Night Tropical New Year's II Cruise
San Juan to Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/28/25
|
From
$6,399
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
12/28/25
|
From
$1,279
|
|
7-night Southern Caribbean Holiday Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
12/28/25
|
From
$921
|
|
7-night A Journey from San Juan to Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
12/29/25
|
From
$5,600
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
12/29/25
|
From
$3,599
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
1/3/26
|
From
$775
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
1/4/26
|
From
$798
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
1/4/26
|
From
$824
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
1/8/26
|
From
$3,799
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
1/10/26
|
From
$581
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
1/11/26
|
From
$778
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
1/11/26
|
From
$600
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
1/17/26
|
From
$678
|