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.
235 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
6-night Bahamian Cruise
San Juan to Galveston |
Cruise Line
Disney Cruise Line
|
Cruise Ship
Disney Magic
|
Departs
11/15/24
|
From
$1,290
|
|
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 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
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
11/17/24
|
From
$501
|
|
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
|
|
7-Night The Glorious Grenadines Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
11/23/24
|
From
$3,999
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
11/23/24
|
From
$1,057
|
|
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 Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
11/24/24
|
Call For Pricing
|
|
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
|
|
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
|
|
7-Night Windward Islands Explorer Cruise
Bridgetown (Barbados) to Marigot, St. Martin |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
11/30/24
|
From
$3,999
|
|
7-Night Best Of British Virgin Islands & St. Barths Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/30/24
|
From
$3,999
|
|
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 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 Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
12/1/24
|
From
$514
|
|
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 Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Celebrity Cruises
|
Cruise Ship
Celebrity Summit
|
Departs
12/7/24
|
From
$987
|
|
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
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
12/8/24
|
From
$587
|