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 |
---|---|---|---|---|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
10/19/25
|
From
$560
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
10/19/25
|
From
$3,599
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
10/26/25
|
From
$550
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
10/29/25
|
From
$3,599
|
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 Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
11/8/25
|
From
$678
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
11/9/25
|
From
$872
|
7-Night Grand Island Adventure Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
11/15/25
|
Call For Pricing
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
11/15/25
|
From
$678
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
11/16/25
|
From
$697
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
11/22/25
|
From
$872
|
7-Night The Glorious Grenadines Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/23/25
|
From
$3,999
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
11/23/25
|
From
$969
|
7-night Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
11/23/25
|
From
$798
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
11/29/25
|
From
$3,399
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
11/29/25
|
From
$775
|
7-Night Windward & British Virgin Islands Cruise
Bridgetown (Barbados) to San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/30/25
|
From
$3,999
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
11/30/25
|
From
$794
|
7-night Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
11/30/25
|
From
$698
|
20-night Southern Caribbean Discovery Cruise
San Juan to Barbados (Bridgetown) |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$7,174
|
12-night Treasures Of Aruba, Bonaire & Curacao Cruise
Roundtrip San Juan |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$4,804
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
12/6/25
|
From
$678
|
7-Night Leeward Islands Adventure Cruise
Roundtrip San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/7/25
|
From
$3,999
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
12/7/25
|
From
$727
|