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.
241 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
4-Night Bahamian Cruise Starting In San Juan Ending In Fort Lauderdale
San Juan to Ft. Lauderdale |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
3/31/25
|
From
$860
|
|
6-night Bahamian Cruise
San Juan to Galveston |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
11/15/24
|
From
$1,212
|
|
6-night San Juan and the Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/3/24
|
From
$2,499
|
|
6-night Western Caribbean Cruise
San Juan to Tampa |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
11/2/25
|
Call For Pricing
|
|
7-night A Journey from San Juan to Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
1/21/25
|
From
$4,350
|
|
7-night A Journey from San Juan to Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
2/28/25
|
From
$4,700
|
|
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
|
|
7-night A Journey from San Juan to Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
3/3/26
|
From
$4,100
|
|
7-night A Journey to Colourful Capitals in the Leeward Antilles Cruise
San Juan to Bridgetown |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
2/21/25
|
From
$4,500
|
|
7-night A Journey to Yacht-filled Harbours and Scenic Sail-ins Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
11/29/24
|
From
$4,500
|
|
7-night A Journey to Yacht-filled Harbours and Scenic Sail-ins Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
3/7/25
|
From
$4,500
|
|
7-Night Best Of British Virgin Islands & St. Barths Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/30/24
|
From
$3,999
|
|
7-Night Best Of British Virgin Islands & St. Barths Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
1/18/25
|
From
$3,999
|
|
7-Night Best Of British Virgin Islands & St.Barths Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
2/22/25
|
From
$4,999
|
|
7-Night British & French Islands Discovery Cruise
Bridgetown (Barbados) to St. Maarten (Philipsburg) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
4/12/25
|
Call For Pricing
|
|
7-night Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
11/23/25
|
From
$798
|
|
7-night Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
11/30/25
|
From
$698
|
|
7-night Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
12/7/25
|
From
$698
|
|
7-Night Caribbean Dream Cruise
San Juan to St. John's, Antigua |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/9/24
|
From
$3,999
|
|
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 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 Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
1/4/26
|
From
$798
|
|
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 Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
1/18/26
|
From
$728
|