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Cruises from San Juan

Choose from 234 unique cruises starting in San Juan, and traveling to Barcelona, Bridgetown, Colon, Fort Lauderdale, Lisbon and more. December is the most popular month to join a cruise from San Juan and you can select from 395 departures available from twelve leading cruise lines.
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234 Cruises (395 Cruise Departures)
11 Day West Indies Explorer with Viking Cruises
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Ships: Viking Sea, Viking Sky
Departures: Nov 2026 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Viking $799 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
Save 450
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Dec 2026 to Apr 2027
Visit: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$973
Oceanview
$1,183
Balcony
$1,393
Suite
$3,703
From
US$973
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 04 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Saint Martin
Inside
$1,139
Oceanview
$1,329
Balcony
$1,549
Suite
$2,349
From
US$1,139
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, Antigua & Barbados with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 21 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+9 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Saint Barthelemy
Azamara Always Included
Inside
-
Oceanview
$3,999
Balcony
$5,179
Suite
$8,059
From
US$3,999
Per Person
View Trip
21 Day Mediterranean & Atlantic Crossing with Viking Cruises
Cruise
 (5)

21 Days (20 Nights) San Juan to Rome
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 06 March 2027
Visit: Puerto Rico, Saint Martin, Portugal, Spain, France, Monaco, Italy
Viking $1,299 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,398
Suite
$11,798
From
US$7,398
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Tortola with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 20 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique, Grenada, Barbados
Princess Standard
Inside
$914
Oceanview
$1,014
Balcony
$1,369
Suite
$1,649
From
US$914
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 14 March 2027
Visit: Puerto Rico, Virgin Islands, Curacao, Aruba
Inside
$1,389
Oceanview
$1,389
Balcony
$1,549
Suite
$2,139
From
US$1,389
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 09 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,543
Oceanview
$1,873
Balcony
$2,168
Suite
$2,958
From
US$1,543
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (10)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 07 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+4 more), Dominica, Barbados, Saint Kitts and Nevis, Grenada
Princess Standard
Inside
$1,516
Oceanview
$1,686
Balcony
$2,516
Suite
$3,146
From
US$1,516
Per Person
View Trip
9 Day Southern Caribbean Cruise: Martinique, Grenada & U.S. Virgin Islands with Azamara Cruises
Cruise
 (5)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,269
Oceanview
$2,829
Balcony
$3,429
Suite
$5,199
From
US$2,269
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 11 March 2028
Visit: Puerto Rico, Virgin Islands, Barbados, Martinique, Dominica, Saint Martin
Inside
$903
Oceanview
$1,043
Balcony
$1,253
Suite
$3,850
From
US$903
Per Person
View Trip
22 Day From the Caribbean to the Amazon with Viking Cruises
Cruise
 (5)

22 Days (21 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 06 January 2028
Visit: Puerto Rico, Barbados, French Guiana, Brazil (+4 more), Trinidad and Tobago, Saint Lucia, Antigua and Barbuda, Virgin Islands
Viking $799 Air Deal
Inside
-
Oceanview
-
Balcony
$12,899
Suite
$32,999
From
US$12,899
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 13 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Lucia, Barbados, Saint Kitts and Nevis, Saint Martin
Inside
$1,259
Oceanview
$1,439
Balcony
$1,649
Suite
$2,439
From
US$1,259
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (10)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Princess Standard
Inside
$689
Oceanview
$639
Balcony
$1,099
Suite
$1,299
From
US$639
Per Person
View Trip
6 Day Southern Caribbean with St. Lucia Holiday with Princess
Cruise
 (1)

6 Days (5 Nights) San Juan to Bridgetown
Cruise Line: Princess
Ship: Emerald Princess
Departure: 21 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Princess Standard
Inside
$653
Oceanview
$724
Balcony
$859
Suite
$1,391
From
US$653
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 06 December 2026
Visit: Puerto Rico, Saint Martin, Saint Lucia, Barbados, Saint Kitts and Nevis, Virgin Islands
Inside
$1,409
Oceanview
$1,459
Balcony
$1,859
Suite
$1,879
From
US$1,409
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Viva
Departure: 16 January 2028
Visit: Puerto Rico, Aruba, Barbados, Saint Martin, Saint Kitts and Nevis
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Tortola Holiday with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$1,034
Oceanview
$1,044
Balcony
$1,389
Suite
$2,149
From
US$1,034
Per Person
View Trip
8 Day Southern Caribbean New Year's Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 26 December 2026
Visit: Puerto Rico, Saint Martin, Martinique, Barbados, Saint Lucia, Antigua and Barbuda
Inside
$1,836
Oceanview
$1,953
Balcony
$2,233
Suite
$4,823
From
US$1,836
Per Person
View Trip
8 Day A Journey Through Beguiling Tropical Elegance To Vibrant Island Delights with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 27 February 2028
Visit: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,020
From
US$4,020
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 06 February 2027
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Inside
$833
Oceanview
$1,113
Balcony
$1,308
Suite
$3,563
From
US$833
Per Person
View Trip
8 Day Sisters at Sea: Valiant Lady with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 13 February 2027
Visit: Puerto Rico, Dominican Republic, Turks and Caicos Islands
Inside
-
Oceanview
$1,533
Balcony
$1,736
Suite
$5,110
From
US$1,533
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Dominica, Antigua and Barbuda, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$756
Oceanview
$826
Balcony
$1,598
Suite
$1,681
From
US$756
Save 422
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 30 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$653
Oceanview
$683
Balcony
$1,293
Suite
$1,421
From
US$653
Save 378
Per Person
View Trip
6 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (10)

6 Days (5 Nights) San Juan to Bridgetown
Cruise Line: Princess
Ship: Crown Princess
Departure: 03 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$772
Oceanview
$879
Balcony
$1,021
Suite
$1,447
From
US$772
Per Person
View Trip
8 Day Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Viva
Departures: Dec 2027 to Dec 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Martin, Curacao, Aruba
Inside
$1,139
Oceanview
$1,329
Balcony
$1,559
Suite
$2,369
From
US$1,139
Per Person
View Trip
15 Day Southern Caribbean Adventurer Holiday with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,853
Oceanview
$1,883
Balcony
$2,448
Suite
$3,568
From
US$1,853
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 05 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Martinique, Dominica
Princess Standard
Inside
$1,338
Oceanview
$1,588
Balcony
$1,978
Suite
$2,518
From
US$1,338
Per Person
View Trip
18 Day Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba with Azamara Cruises
Cruise
 (5)

18 Days (17 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+10 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Bonaire, Curacao, Aruba, Dominican Republic, Bahamas, USA
Azamara Always Included
Inside
$4,729
Oceanview
$5,809
Balcony
$7,139
Suite
$10,859
From
US$4,729
Per Person
View Trip
9 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 March 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Dominica, Saint Martin
Inside
$1,272
Oceanview
$1,512
Balcony
$1,752
Suite
$4,552
From
US$1,272
Per Person
View Trip
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