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 |
|---|---|---|---|---|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
1/25/26
|
From
$728
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
2/1/26
|
From
$748
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
2/8/26
|
From
$778
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
2/15/26
|
From
$848
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
2/22/26
|
From
$828
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
3/1/26
|
From
$878
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
3/8/26
|
From
$848
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
3/15/26
|
From
$878
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
3/22/26
|
From
$878
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
3/29/26
|
From
$878
|
|
7-night Eastern & Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
4/5/26
|
From
$878
|
|
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 Eternal Sunshine Cruise
Roundtrip San Juan |
Cruise Line
Regent Seven Seas Cruises
|
Cruise Ship
Seven Seas Navigator
|
Departs
1/30/25
|
From
$3,599
|
|
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 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 Grand Island Adventure Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
11/15/25
|
Call For Pricing
|
|
7-Night Grand Island Adventure Cruise
San Juan to St. Thomas (Charlotte Amalie) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/14/25
|
From
$3,999
|
|
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
|
|
7-night Joy of the Islands Cruise
Roundtrip San Juan |
Cruise Line
Regent Seven Seas Cruises
|
Cruise Ship
Seven Seas Navigator
|
Departs
1/13/25
|
From
$3,599
|
|
7-night Leeward Islands Adventure Cruise
Roundtrip San Juan |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
2/15/25
|
Call For Pricing
|
|
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 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
|
|
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
$2,699
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
9/15/24
|
From
$495
|