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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 322 departures available from ten of the world's leading cruise lines.
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167 Cruises (322 Cruise Departures)
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
Departures: Jan 2028 to Mar 2028
Visit: Puerto Rico, Aruba, Saint Lucia, 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 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
$774
Oceanview
$1,054
Balcony
$1,264
Suite
$1,799
From
US$774
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: 20 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,893
Oceanview
$2,093
Balcony
$2,778
Suite
$3,398
From
US$1,893
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: 25 December 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Barbados, Antigua and Barbuda, Saint Martin, Virgin Islands
Inside
$1,909
Oceanview
$2,149
Balcony
$2,429
Suite
$3,499
From
US$1,909
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: 10 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+4 more), Saint Lucia, Barbados, Martinique, Grenada
Princess Standard
Inside
$1,611
Oceanview
$1,701
Balcony
$2,986
Suite
$3,946
From
US$1,611
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: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$598
Oceanview
$750
Balcony
$1,149
Suite
$1,604
From
US$598
Save 555
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
$1,323
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: 03 January 2027
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao
Inside
$1,839
Oceanview
$1,889
Balcony
$1,959
Suite
$2,249
From
US$1,839
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
$1,603
Balcony
$1,802
Suite
$5,110
From
US$1,603
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
$1,883
Balcony
$2,163
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: 15 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados, Saint Kitts and Nevis, Saint Martin
Inside
$1,779
Oceanview
$2,009
Balcony
$2,159
Suite
$2,499
From
US$1,779
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
Departure: 14 November 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Curacao, Aruba
Inside
$1,219
Oceanview
$1,399
Balcony
$1,609
Suite
$2,399
From
US$1,219
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: 15 December 2026
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
$12,499
Suite
$32,999
From
US$12,499
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 February 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Kitts and Nevis, Saint Martin
Inside
$1,419
Oceanview
$1,539
Balcony
$1,789
Suite
$2,519
From
US$1,419
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia Holiday with Princess
Cruise
 (10)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Emerald Princess
Departures: Dec 2026 to Dec 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Princess Standard
Inside
$774
Oceanview
$974
Balcony
$1,174
Suite
$1,899
From
US$774
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
$1,505
From
US$710
Save 400
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
$1,643
Oceanview
$1,973
Balcony
$2,368
Suite
$3,208
From
US$1,643
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
$1,953
Oceanview
$1,983
Balcony
$2,648
Suite
$3,818
From
US$1,953
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
Departure: 05 December 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Barbados, Aruba
Inside
$1,099
Oceanview
$1,289
Balcony
$1,509
Suite
$2,309
From
US$1,099
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
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
$1,521
Oceanview
$1,661
Balcony
$2,446
Suite
$3,058
From
US$1,521
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
$664
Oceanview
$834
Balcony
$1,034
Suite
$1,399
From
US$664
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
$1,179
Oceanview
$1,369
Balcony
$1,599
Suite
$2,409
From
US$1,179
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
$1,084
Oceanview
$1,094
Balcony
$1,464
Suite
$2,249
From
US$1,084
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: 07 March 2027
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao
Inside
$1,439
Oceanview
$1,489
Balcony
$1,809
Suite
$2,169
From
US$1,439
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: 21 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Martinique, Dominica, Grenada
Princess Standard
Inside
$1,517
Oceanview
$1,497
Balcony
$2,632
Suite
$3,632
From
US$1,497
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
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Lucia, Dominica, 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
 (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
$1,591
Oceanview
$1,761
Balcony
$2,666
Suite
$3,346
From
US$1,591
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
$1,853
Oceanview
$2,123
Balcony
$2,788
Suite
$4,118
From
US$1,853
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

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 with Virgin Voyages
Cruise
 (2)

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
$1,507
Suite
$3,983
From
US$1,043
Per Person
View Trip
Results: 31-60 of 167

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