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 |
|---|---|---|---|---|
|
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 Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
2/21/26
|
From
$667
|
|
7-night Caribbean Cruise: Barbados, Antigua & St. Lucia
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
2/22/26
|
From
$841
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
2/22/26
|
From
$2,020
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
2/22/26
|
From
$1,068
|
|
14-night Eastern and Southern Caribbean Cruise
San Juan to Ft. Lauderdale |
Cruise Line
Silversea Cruises
|
Cruise Ship
Silver Ray
|
Departs
2/24/26
|
Call For Pricing
|
|
7-night Windward Islands Surf & Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/27/26
|
From
$3,436
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
2/27/26
|
From
$14,799
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/27/26
|
From
$4,299
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
2/28/26
|
From
$689
|
|
7-night Caribbean Cruise: Barbados, Antigua & St. Lucia
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
3/1/26
|
From
$821
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
3/1/26
|
From
$689
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
3/1/26
|
From
$1,004
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
3/1/26
|
From
$1,990
|
|
7-night A Journey Into Tropical Utopia & Spanish Legacy With Art Deco Flair
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
3/2/26
|
From
$3,635
|
|
8-night A Journey of Cultural Immersions in the Caribbean
Roundtrip San Juan |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
3/3/26
|
From
$4,700
|
|
15-night An Extended Journey Through Spectacular Nature And Historic Wonders
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
3/3/26
|
From
$7,920
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
3/6/26
|
From
$7,562
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
3/6/26
|
From
$13,696
|
|
5-night Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Ilma
|
Departs
3/6/26
|
Call For Pricing
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
3/7/26
|
From
$642
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
3/8/26
|
From
$835
|
|
14-night Southern Caribbean Adventurer Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
3/8/26
|
From
$1,980
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
3/8/26
|
From
$1,044
|