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.
240 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
6-night San Juan and the Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/3/24
|
From
$2,499
|
|
13-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/3/24
|
From
$4,399
|
|
7-night Windward Islands Surf and Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/9/24
|
From
$2,899
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/9/24
|
From
$4,399
|
|
7-night San Juan and the Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/16/24
|
From
$2,499
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/16/24
|
From
$3,999
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/23/24
|
From
$4,199
|
|
7-night Windward Islands Surf and Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/23/24
|
From
$2,499
|
|
7-night San Juan and the Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/30/24
|
From
$2,599
|
|
7-night Winter Antilles Escape Cruise
San Juan to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/7/24
|
From
$2,499
|
|
14-night Star Collector – White Sands of the Windward Islands Cruise
San Juan to Oranjestad, Aruba |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/7/24
|
From
$3,999
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
10/30/24
|
From
$4,499
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
11/9/24
|
From
$4,299
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
11/19/24
|
From
$3,999
|
|
12-night Amazon and Caribbean Adventure Cruise
San Juan to Manaus (Amazon River) |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
11/29/24
|
From
$4,799
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
12/23/24
|
From
$4,599
|
|
12-night Amazon and Caribbean Adventure Cruise
San Juan to Manaus (Amazon River) |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
1/2/25
|
From
$4,799
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
1/26/25
|
From
$5,699
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/5/25
|
From
$4,799
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/15/25
|
From
$4,999
|
|
12-night Amazon and Caribbean Adventure Cruise
San Juan to Manaus (Amazon River) |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/25/25
|
From
$5,099
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/21/25
|
From
$4,799
|
|
17-night West Indies and Panama Canal Passage Cruise
San Juan to Los Angeles |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/31/25
|
From
$5,999
|
|
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
|