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.
246 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
7-night Grand Island Adventure Cruise
St. Thomas (Charlotte Amalie) to San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
1/31/26
|
From
$4,399
|
|
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
|
|
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
|
|
7-Night The Glorious Grenadines Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
1/11/25
|
From
$4,299
|
|
7-Night Spanish & British Caribbean Delight Cruise
Roundtrip San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
1/11/25
|
From
$4,299
|
|
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
|
|
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
$4,050
|
|
7-Night Caribbean Dream Cruise
San Juan to St. John's, Antigua |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/9/24
|
From
$3,999
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
11/9/24
|
From
$3,999
|
|
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
|
|
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
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/23/24
|
From
$3,999
|
|
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
|
|
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 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
1/18/25
|
From
$3,999
|
|
7-Night French West Indies & The Grenadines Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
3/1/25
|
From
$3,999
|
|
7-Night Windward & British Virgin Islands Cruise
Bridgetown (Barbados) to St. Maarten (Philipsburg) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
3/8/25
|
From
$3,999
|
|
7-Night French West Indies & The Grenadines Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
3/22/25
|
From
$3,999
|
|
7-Night The Glorious Grenadines Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/23/25
|
From
$3,999
|
|
7-Night Windward & British Virgin Islands Cruise
Bridgetown (Barbados) to San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
11/30/25
|
From
$3,999
|
|
7-Night Leeward Islands Adventure Cruise
Roundtrip San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/7/25
|
From
$3,999
|
|
7-Night Spanish & British Caribbean Delight Cruise
San Juan to St. Maarten (Philipsburg) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
12/13/25
|
From
$3,999
|