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 Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
8/29/26
|
From
$803
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
9/5/26
|
From
$800
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
9/12/26
|
From
$777
|
|
11-night Southern & Eastern Caribbean Cruise
San Juan to New York City |
Cruise Line
Crystal Cruises
|
Cruise Ship
Crystal Symphony
|
Departs
9/14/26
|
From
$5,500
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
9/19/26
|
From
$770
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
9/26/26
|
From
$747
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
10/3/26
|
From
$747
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
10/10/26
|
From
$724
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
10/17/26
|
From
$727
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
10/24/26
|
From
$705
|
|
11-night Gems Of The Leeward Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
10/28/26
|
From
$3,657
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
10/31/26
|
From
$737
|
|
7-night A Journey Into Caribbean Exploration & Island Delights
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA III
|
Departs
11/1/26
|
From
$3,845
|
|
7-night Eastern Caribbean Cruise
San Juan to Ft. Lauderdale |
Cruise Line
Crystal Cruises
|
Cruise Ship
Crystal Symphony
|
Departs
11/4/26
|
From
$3,600
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
11/5/26
|
From
$3,799
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
11/7/26
|
From
$735
|
|
14-night Caribbean Voyage: San Juan, St. Lucia & St. Kitts
Roundtrip San Juan |
Cruise Line
Azamara Cruises
|
Cruise Ship
Azamara Journey
|
Departs
11/7/26
|
From
$2,549
|
|
7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados
San Juan to Bridgetown (Barbados) |
Cruise Line
Azamara Cruises
|
Cruise Ship
Azamara Journey
|
Departs
11/7/26
|
From
$1,299
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/8/26
|
From
$4,093
|
|
7-night Windward Islands Surf & Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/8/26
|
From
$2,530
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Radiance of the Seas
|
Departs
11/14/26
|
From
$743
|
|
7-night Caribbean Cruise: Curacao & Aruba
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Breakaway
|
Departs
11/15/26
|
From
$1,240
|
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/15/26
|
From
$4,093
|
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/15/26
|
From
$2,562
|