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 |
|---|---|---|---|---|
|
10-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
2/1/26
|
From
$1,249
|
|
4-night Eastern Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Ilma
|
Departs
2/4/26
|
Call For Pricing
|
|
7-night A Journey into the Caribbean’s Most Desirable Shores
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
2/5/26
|
From
$3,915
|
|
15-night A Grand Journey Through Caribbean Serenity And Tropical Treasures
Roundtrip San Juan |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
2/5/26
|
From
$7,720
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/6/26
|
From
$3,962
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/6/26
|
From
$6,590
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
2/7/26
|
From
$689
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/7/26
|
From
$4,599
|
|
7-night Caribbean Cruise: Barbados, Antigua & St. Lucia
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
2/8/26
|
From
$891
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
2/8/26
|
From
$2,324
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
2/8/26
|
From
$1,068
|
|
7-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Ilma
|
Departs
2/8/26
|
Call For Pricing
|
|
7-night Windward Islands Surf & Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/13/26
|
From
$3,427
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/13/26
|
From
$5,890
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
2/14/26
|
From
$744
|
|
7-night Grand Island Adventure Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
2/14/26
|
From
$5,019
|
|
7-night Caribbean Cruise: Barbados, Antigua & St. Lucia
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
2/15/26
|
From
$861
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
2/15/26
|
From
$2,074
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
2/15/26
|
From
$1,228
|
|
7-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Ilma
|
Departs
2/15/26
|
Call For Pricing
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/17/26
|
From
$4,599
|
|
9-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
2/20/26
|
From
$905
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/20/26
|
From
$3,462
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/20/26
|
From
$5,799
|