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.
236 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
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
10/12/24
|
From
$1,057
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
10/19/24
|
From
$971
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
10/26/24
|
From
$971
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
11/2/24
|
From
$971
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
11/9/24
|
From
$1,041
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
11/16/24
|
From
$1,016
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
11/23/24
|
From
$1,057
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
11/30/24
|
From
$1,053
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
12/7/24
|
From
$987
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
12/14/24
|
From
$1,057
|
|
7-night Southern Caribbean Holiday
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
12/21/24
|
From
$1,256
|
|
7-night Southern Caribbean Holiday
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
12/28/24
|
From
$1,230
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Crystal Cruises
|
Cruise Ship
Crystal Serenity
|
Departs
12/4/24
|
From
$3,100
|
|
7-night Eastern Caribbean Cruise
San Juan to Ft. Lauderdale |
Cruise Line
Crystal Cruises
|
Cruise Ship
Crystal Serenity
|
Departs
12/11/24
|
From
$3,100
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
11/8/24
|
From
$1,953
|
|
6-night Bahamian Cruise
San Juan to Galveston |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
11/15/24
|
From
$1,290
|
|
4-Night Bahamian Cruise Starting In San Juan Ending In Fort Lauderdale
San Juan to Ft. Lauderdale |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
3/31/25
|
From
$860
|
|
7-night A Journey to Yacht-filled Harbours and Scenic Sail-ins Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
11/29/24
|
From
$4,500
|
|
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
$8,500
|
|
9-night A Journey From San Juan To Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
12/27/24
|
From
$7,200
|
|
7-night A Journey from San Juan to Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
1/21/25
|
From
$4,350
|
|
7-night A Journey to Colourful Capitals in the Leeward Antilles Cruise
San Juan to Bridgetown |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
2/21/25
|
From
$4,500
|
|
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
$8,500
|
|
7-night A Journey from San Juan to Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
Explora I
|
Departs
2/28/25
|
From
$4,700
|