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.
238 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
7-Night Windward & British Virgin Islands Cruise
Bridgetown (Barbados) to St. Maarten (Philipsburg) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
1/18/25
|
From
$4,599
|
|
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 Southern Caribbean: Barbados, Antigua & St. Lucia Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Viva
|
Departs
1/19/25
|
From
$1,418
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
1/19/25
|
From
$501
|
|
10-night Barefoot Reverie Cruise
Roundtrip San Juan |
Cruise Line
Regent Seven Seas Cruises
|
Cruise Ship
Seven Seas Navigator
|
Departs
1/20/25
|
From
$5,099
|
|
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 Southern Caribbean: Curacao & Aruba Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Viva
|
Departs
1/26/25
|
From
$1,548
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
1/26/25
|
Call For Pricing
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
1/26/25
|
From
$425
|
|
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 Southern Caribbean: Curacao & Aruba Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Viva
|
Departs
2/2/25
|
From
$1,569
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
2/2/25
|
From
$438
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/5/25
|
From
$11,499
|
|
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
|
|
7-night Southern Caribbean: Barbados, Antigua & St. Lucia Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Viva
|
Departs
2/9/25
|
From
$1,519
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
2/9/25
|
From
$520
|
|
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
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/15/25
|
From
$7,999
|
|
7-Night West Indies Explorer Cruise
Bridgetown (Barbados) to St. John's, Antigua |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream I
|
Departs
2/15/25
|
Call For Pricing
|
|
7-night Southern Caribbean: Curacao & Aruba Cruise
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Viva
|
Departs
2/16/25
|
From
$1,708
|
|
10-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Rhapsody of the Seas
|
Departs
2/16/25
|
Call For Pricing
|
|
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 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
2/22/25
|
From
$4,599
|