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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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170 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
Inside
-
Oceanview
-
Balcony
$3,799
Suite
$5,999
From
US$3,799
Per Person
View Trip
8 Day Southern Caribbean New Year's Cruise with Virgin Voyages
Cruise
 (1)

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 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: 23 January 2028
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Bonaire, Curacao
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (9)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 28 February 2027
Visit: Puerto Rico, Saint Martin, Martinique, Dominica (+5 more), Grenada, Barbados, Virgin Islands, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,582
Oceanview
$1,742
Balcony
$2,362
Suite
$3,032
From
US$1,582
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
$1,359
Oceanview
$1,459
Balcony
$1,729
Suite
$1,929
From
US$1,359
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
$3,799
Oceanview
$4,809
Balcony
$5,859
Suite
$8,929
From
US$3,799
Per Person
View Trip
8 Day Southern Caribbean Cruise New Year’s with Virgin Voyages
Cruise
 (1)

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 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
$689
Oceanview
$766
Balcony
$1,248
Suite
$1,448
From
US$689
Save 568
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (1)

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
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$3,983
From
US$1,043
Per Person
View Trip
8 Day Southern Caribbean 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 December 2026
Visit: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Barbados, Saint Lucia, Virgin Islands
Inside
$1,419
Oceanview
$1,539
Balcony
$1,649
Suite
$1,959
From
US$1,419
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: 22 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
8 Day Southern Caribbean 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
Departures: Nov 2026 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Saint Martin
Inside
$1,259
Oceanview
$1,459
Balcony
$1,639
Suite
$2,069
From
US$1,259
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
$3,655
From
US$3,655
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (9)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 31 January 2027
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$1,542
Oceanview
$1,532
Balcony
$2,552
Suite
$3,352
From
US$1,532
Per Person
View Trip
9 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 12 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Dominica, Saint Martin
Inside
$952
Oceanview
$1,112
Balcony
$1,512
Suite
$4,320
From
US$952
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
Departures: Mar 2027 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Inside
$1,259
Oceanview
$1,459
Balcony
$1,709
Suite
$2,369
From
US$1,259
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
$1,159
Oceanview
$1,259
Balcony
$1,674
Suite
$2,269
From
US$1,159
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: 03 January 2027
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao
Inside
$1,719
Oceanview
$1,779
Balcony
$1,769
Suite
$2,199
From
US$1,719
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: Valiant Lady
Departure: 02 January 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Lucia, Antigua and Barbuda, Saint Martin
Inside
$973
Oceanview
$1,183
Balcony
$1,463
Suite
$3,983
From
US$973
Per Person
View Trip
8 Day Southern Caribbean 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: 09 January 2028
Visit: Puerto Rico, Saint Martin, Curacao, Saint Lucia, 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 & Aruban Nights with Virgin Voyages
Cruise
 (1)

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
$1,304
Suite
$3,850
From
US$833
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 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: 17 January 2027
Visit: Puerto Rico, Bonaire, Curacao, Virgin Islands
Inside
$1,359
Oceanview
$1,429
Balcony
$1,559
Suite
$2,009
From
US$1,359
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: 14 November 2026
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Saint Kitts and Nevis, Virgin Islands
Exclusive Savings
Inside
$686
Oceanview
$752
Balcony
$1,247
Suite
$1,439
From
US$686
Save 492
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
$1,519
Oceanview
$1,579
Balcony
$1,719
Suite
$2,009
From
US$1,519
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: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$2,008
Oceanview
$2,408
Balcony
$3,148
Suite
$4,118
From
US$2,008
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: Valiant Lady
Departure: 20 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Lucia, Barbados, Dominica, Saint Martin
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$3,983
From
US$1,043
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: 12 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique, Dominica, Barbados
Princess Standard
Inside
$649
Oceanview
$849
Balcony
$1,024
Suite
$1,399
From
US$649
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
$1,348
Oceanview
$1,668
Balcony
$2,068
Suite
$2,698
From
US$1,348
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
$1,679
Oceanview
$1,779
Balcony
$2,159
Suite
$2,619
From
US$1,679
Per Person
View Trip
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