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Round-trip Cruises from San Juan

Are you looking for a cruise starting and ending in San Juan? December is the most popular month to join a roundtrip cruise from San Juan and we have 319 departures available from ten of the world's leading cruise lines.
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162 Cruises (319 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
$3,799
Suite
$5,999
From
US$3,799
Save 450
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: 27 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Saint Lucia, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$710
Oceanview
$770
Balcony
$1,320
Suite
$1,480
From
US$710
Save 400
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: Scarlet Lady
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (11)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 24 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Guadeloupe, Dominica, Grenada
Princess Standard
Inside
$1,522
Oceanview
$1,522
Balcony
$2,672
Suite
$3,472
From
US$1,522
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
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,448
From
US$674
Save 552
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: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Antigua and Barbuda, Saint Martin
Inside
$1,259
Oceanview
$1,459
Balcony
$1,709
Suite
$2,609
From
US$1,259
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, St. Lucia & St. Kitts with Azamara Cruises
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2026 to Dec 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin
Azamara Always Included
Inside
$4,209
Oceanview
$4,399
Balcony
$5,899
Suite
$8,639
From
US$4,209
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (11)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 17 January 2027
Visit: Puerto Rico, Saint Martin, Martinique, Grenada (+4 more), Saint Lucia, Barbados, Virgin Islands, Antigua and Barbuda
Princess Standard
Inside
$1,696
Oceanview
$1,766
Balcony
$3,066
Suite
$3,966
From
US$1,696
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 21 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin
Azamara Always Included
Inside
$3,849
Oceanview
$4,869
Balcony
$5,919
Suite
$8,989
From
US$3,849
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (11)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Jan 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
$1,516
Oceanview
$1,736
Balcony
$2,528
Suite
$2,908
From
US$1,516
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 02 January 2028
Visit: Puerto Rico, Saint Vincent, Barbados, Dominica, Saint Martin
Inside
$654
Oceanview
$774
Balcony
$1,074
Suite
$3,300
From
US$654
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: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Martin, Barbados
Inside
$1,259
Oceanview
$1,459
Balcony
$1,709
Suite
$2,609
From
US$1,259
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: 31 January 2027
Visit: Puerto Rico, Curacao, Aruba, Virgin Islands
Inside
$1,489
Oceanview
$1,489
Balcony
$1,689
Suite
$1,859
From
US$1,489
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
Departures: Jun 2026 to Jul 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominican Republic
Exclusive Savings
Inside
$1,404
Oceanview
$1,464
Balcony
$2,904
Suite
$3,399
From
US$1,404
Save 876
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: 10 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Barbados, Saint Lucia, Saint Kitts and Nevis
Inside
$1,559
Oceanview
$1,609
Balcony
$1,709
Suite
$1,869
From
US$1,559
Per Person
View Trip
9 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 31 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda, Saint Vincent
Bonus Onboard Credit
Exclusive Savings
Inside
$1,378
Oceanview
$1,578
Balcony
$2,641
Suite
$3,050
From
US$1,378
Save 687
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
$1,399
Oceanview
$1,389
Balcony
$1,549
Suite
$2,089
From
US$1,389
Per Person
View Trip
8 Day Southern Caribbean Cruise New Year’s with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 26 December 2027
Visit: Puerto Rico, Saint Martin, Barbados, Martinique, Antigua and Barbuda, Virgin Islands
Inside
$1,673
Oceanview
$1,813
Balcony
$2,093
Suite
$4,480
From
US$1,673
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
$1,489
Oceanview
$1,539
Balcony
$1,809
Suite
$1,939
From
US$1,489
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts with Princess
Cruise
 (11)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 28 February 2027
Visit: Puerto Rico, Saint Martin, Martinique, Dominica, Grenada, Barbados
Princess Standard
Inside
$699
Oceanview
$849
Balcony
$1,174
Suite
$1,749
From
US$699
Per Person
View Trip
8 Day A Journey Across Caribbean Culture & Volcanic Landscapes with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 16 January 2028
Visit: Puerto Rico, Saint Vincent, Saint Lucia, Barbados, Antigua and Barbuda, Saint Kitts and Nevis
Inside
-
Oceanview
-
Balcony
-
Suite
$4,020
From
US$4,020
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 16 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Barbados, Saint Lucia
Princess Standard
Inside
$829
Oceanview
$1,099
Balcony
$1,274
Suite
$1,879
From
US$829
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
$949
Oceanview
$1,049
Balcony
$1,474
Suite
$1,779
From
US$949
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: Scarlet Lady
Departure: 11 December 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Lucia, Aruba
Inside
$833
Oceanview
$973
Balcony
$1,305
Suite
$3,850
From
US$833
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: 11 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Martin, Barbados
Inside
$1,189
Oceanview
$1,369
Balcony
$1,599
Suite
$2,409
From
US$1,189
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Antigua and Barbuda, Saint Martin
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
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: 28 February 2027
Visit: Puerto Rico, Virgin Islands, Dominica, Barbados, Saint Martin
Inside
$1,369
Oceanview
$1,449
Balcony
$1,699
Suite
$1,819
From
US$1,369
Per Person
View Trip
9 Day Southern Caribbean & Aruban Holidays with Virgin Voyages
Cruise
 (2)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 18 December 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Aruba, Curacao
Inside
$1,112
Oceanview
$1,272
Balcony
$1,592
Suite
$4,960
From
US$1,112
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: 15 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados, Saint Kitts and Nevis, Saint Martin
Inside
$1,859
Oceanview
$2,009
Balcony
$2,059
Suite
$2,379
From
US$1,859
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 28 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Inside
$1,043
Oceanview
$1,239
Balcony
$1,113
Suite
$2,863
From
US$1,043
Per Person
View Trip
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