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.
247 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
21-night Caribbean and Riviera Revelry Voyage
San Juan to Rome (Civitavecchia) |
Cruise Line
Oceania Cruises
|
Cruise Ship
Sirena
|
Departs
4/22/25
|
From
$4,699
|
|
20-night Southern Caribbean Discovery Cruise
San Juan to Barbados (Bridgetown) |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$7,174
|
|
20-night Holiday Caribbean Enchantment Cruise
San Juan to Bridgetown (Barbados) |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/14/25
|
From
$8,004
|
|
18-night Eastern Caribbean Voyage
San Juan to Miami |
Cruise Line
Azamara
|
Cruise Ship
Azamara Quest
|
Departs
12/19/25
|
From
$3,120
|
|
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
|
|
15-night Caribbean & Panama Canal Cruise
San Juan to Los Angeles |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/29/26
|
From
$5,499
|
|
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
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/9/24
|
From
$4,299
|
|
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
|
|
14-night Exotic Atlantic Crossing Voyage
San Juan to Barcelona |
Cruise Line
Oceania Cruises
|
Cruise Ship
Sirena
|
Departs
4/22/25
|
From
$3,099
|
|
14-night Eastern Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Azamara
|
Cruise Ship
Azamara Quest
|
Departs
11/8/25
|
From
$2,320
|
|
14-night Eastern Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Azamara
|
Cruise Ship
Azamara Quest
|
Departs
11/22/25
|
From
$2,320
|
|
14-night An Extended Journey To Tropical Splendor Cruise
San Juan to Bridgetown |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
11/29/24
|
From
$7,600
|
|
14-night An Extended Journey Of Caribbean Culture And Tropical Trails Cruise
Roundtrip San Juan |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
2/21/25
|
From
$5,500
|
|
13-night Transatlantic: Dominican Republic & Spain Cruise
San Juan to Lisbon |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Viva
|
Departs
4/13/25
|
From
$1,398
|
|
13-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/3/24
|
From
$4,299
|
|
13-night Eastern Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Azamara
|
Cruise Ship
Azamara Quest
|
Departs
12/6/25
|
From
$2,320
|
|
12-night Treasures Of Aruba, Bonaire & Curacao Cruise
Roundtrip San Juan |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$4,804
|
|
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
$4,899
|
|
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
|
|
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
|
|
11-night Caribbean Warmth Cruise
San Juan to Miami, Florida |
Cruise Line
Regent Seven Seas Cruises
|
Cruise Ship
Seven Seas Navigator
|
Departs
2/6/25
|
From
$6,149
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
10/30/24
|
From
$4,099
|