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 Windward Islands Surf & Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/20/26
|
From
$2,730
|
|
12-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Silversea Cruises
|
Cruise Ship
Silver Shadow
|
Departs
12/22/26
|
From
$6,750
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
12/26/26
|
From
$1,022
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Constellation
|
Departs
12/26/26
|
From
$1,499
|
|
7-night Tropical New Year's II Explorer Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/27/26
|
From
$10,419
|
|
7-night Southern Caribbean Holiday Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
12/27/26
|
From
$1,035
|
|
7-night Southern Caribbean Cruise With Barbados
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Crown Princess
|
Departs
12/27/26
|
From
$1,518
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Crown Princess
|
Departs
12/27/26
|
From
$2,710
|
|
7-night Caribbean Cruise: Barbados, St. Lucia & St. Thomas
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Breakaway
|
Departs
12/27/26
|
From
$1,466
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/27/26
|
From
$4,193
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/27/26
|
From
$2,762
|
|
8-night A Journey Of Spectacular Festivities & Caribbean Wonders
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA III
|
Departs
12/28/26
|
From
$6,000
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
1/2/27
|
From
$885
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Constellation
|
Departs
1/2/27
|
From
$1,044
|
|
6-night St. Barths Getaway Cruise
Roundtrip San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
1/3/27
|
From
$3,959
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
1/3/27
|
From
$861
|
|
7-night Southern Caribbean Cruise With Barbados
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Crown Princess
|
Departs
1/3/27
|
From
$1,218
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Crown Princess
|
Departs
1/3/27
|
From
$2,410
|
|
7-night Eastern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Silversea Cruises
|
Cruise Ship
Silver Shadow
|
Departs
1/3/27
|
From
$3,950
|
|
7-night Caribbean Cruise: Curacao & Aruba
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Breakaway
|
Departs
1/3/27
|
From
$1,210
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
1/3/27
|
From
$4,093
|
|
7-night Windward Islands Surf & Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
1/3/27
|
From
$2,530
|
|
7-night A Journey Of Caribbean Delicacies & Idyllic Islands
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
1/4/27
|
From
$3,845
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
1/5/27
|
From
$3,799
|