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.
498 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
49-night Star Collector: Grand Caribbean & Americas Explorer Cruise
San Juan to Juneau |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
3/27/26
|
From
$20,903
|
|
10-night Gems Of The Leeward Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
3/27/26
|
From
$4,157
|
|
17-night Star Collector: Seeking The Antilles Cruise
San Juan to Colon (Panama) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
3/27/26
|
From
$5,884
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
3/28/26
|
From
$821
|
|
7-night Eastern & Southern Caribbean Voyage
Roundtrip San Juan |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Evrima
|
Departs
3/28/26
|
Call For Pricing
|
|
7-night Caribbean Cruise: Barbados, Antigua & St. Lucia
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
3/29/26
|
From
$951
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
3/29/26
|
From
$904
|
|
7-night Southern Caribbean with Barbados Cruise
Roundtrip San Juan |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
3/29/26
|
From
$1,088
|
|
18-night Southern Caribbean Adventurer Cruise
San Juan to Ft. Lauderdale |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
3/29/26
|
From
$2,704
|
|
14-night West Indies To Iberia Cruise
San Juan to Barcelona |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/29/26
|
From
$3,599
|
|
21-night Mediterranean To Caribbean Sojourn Cruise
San Juan to Rome (Civitavecchia) |
Cruise Line
Viking Cruises
|
Cruise Ship
Viking Sea (Ocean)
|
Departs
3/29/26
|
From
$8,148
|
|
7-night Turks & Caicos Cruise
San Juan to Palm Beach |
Cruise Line
SeaDream Yacht Club
|
Cruise Ship
SeaDream II
|
Departs
3/29/26
|
From
$6,119
|
|
7-night A Journey of Coconut Days and Daiquiri Nights
San Juan to Miami |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
4/2/26
|
From
$3,310
|
|
23-night A Grand Journey From Caribbean Delights To Iberian Spectacle
San Juan to Barcelona |
Cruise Line
Explora Journeys
|
Cruise Ship
EXPLORA II
|
Departs
4/2/26
|
From
$9,540
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
4/4/26
|
From
$923
|
|
7-night Caribbean Cruise: Barbados, Antigua & St. Lucia
Roundtrip San Juan |
Cruise Line
Norwegian Cruise Line
|
Cruise Ship
Norwegian Epic
|
Departs
4/5/26
|
From
$1,011
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Brilliance of the Seas
|
Departs
4/5/26
|
From
$962
|
|
11-night Southern Caribbean Islander Cruise
San Juan to Ft. Lauderdale |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
4/5/26
|
From
$1,538
|
|
27-night Panama Canal and Caribbean Adventurer Cruise
San Juan to Los Angeles |
Cruise Line
Princess Cruises
|
Cruise Ship
Grand Princess
|
Departs
4/5/26
|
From
$4,308
|
|
7-night New World Caribbean Trio Cruise
San Juan to Colon (Panama) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
4/6/26
|
From
$3,226
|
|
14-night Star Collector: Rainforest Refuges Of Panama & Costa Rica Via The Panama Canal Cruise
San Juan to Puntarenas |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
4/6/26
|
From
$6,080
|
|
22-night Star Collector Cruise: Central American Explorations Via The Panama Canal
San Juan to Puerto Vallarta |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Seeker
|
Departs
4/6/26
|
From
$8,905
|
|
7-night Southern Caribbean Cruise
Roundtrip San Juan |
Cruise Line
Royal Caribbean International
|
Cruise Ship
Jewel of the Seas
|
Departs
4/11/26
|
From
$826
|
|
12-night Transatlantic Voyage
San Juan to Lisbon |
Cruise Line
Ritz-Carlton Yacht Collection
|
Cruise Ship
Evrima
|
Departs
4/11/26
|
Call For Pricing
|