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.
240 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
20-night Holiday Caribbean Enchantment Cruise
San Juan to Bridgetown (Barbados) |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/14/25
|
From
$8,004
|
|
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
|
|
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
$7,600
|
|
20-night Southern Caribbean Discovery Cruise
San Juan to Barbados (Bridgetown) |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$7,174
|
|
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
$6,480
|
|
7-Night Tropical New Year's II Cruise
San Juan to Bridgetown (Barbados) |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
12/28/25
|
From
$6,399
|
|
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
|
|
17-night West Indies and Panama Canal Passage Cruise
San Juan to Los Angeles |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/31/25
|
From
$5,999
|
|
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
$5,500
|
|
15-night Caribbean & Panama Canal Cruise
San Juan to Los Angeles |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/29/26
|
From
$5,499
|
|
10-night Turquoise Shores, Hidden Isles Cruise
Roundtrip San Juan |
Cruise Line
Regent Seven Seas Cruises
|
Cruise Ship
Seven Seas Navigator
|
Departs
1/3/25
|
From
$5,099
|
|
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
|
|
12-night Amazon and Caribbean Adventure Cruise
San Juan to Manaus (Amazon River) |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
2/25/25
|
From
$5,099
|
|
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
$4,999
|
|
7-Night Turks & Caicos Cruise
San Juan to West Palm Beach |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
3/29/25
|
From
$4,999
|
|
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
$4,899
|
|
12-night Treasures Of Aruba, Bonaire & Curacao Cruise
Roundtrip San Juan |
Cruise Line
Seabourn
|
Cruise Ship
Seabourn Ovation
|
Departs
12/2/25
|
From
$4,804
|
|
12-night Amazon and Caribbean Adventure Cruise
San Juan to Manaus (Amazon River) |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
1/2/25
|
From
$4,799
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/21/25
|
From
$4,799
|
|
7-night A Journey from San Juan to Miami Cruise
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
12/29/25
|
From
$4,760
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
12/23/24
|
From
$4,699
|
|
21-night Caribbean and Riviera Revelry Voyage
San Juan to Rome (Civitavecchia) |
Cruise Line
Oceania Cruises
|
Cruise Ship
Sirena
|
Departs
4/22/25
|
From
$4,699
|
|
10-night West Indies Explorer Cruise
Roundtrip San Juan |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
10/30/24
|
From
$4,599
|
|
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
|