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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 324 departures available from ten of the world's leading cruise lines.
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169 Cruises (324 Cruise Departures)
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
$1,439
Oceanview
$1,509
Balcony
$1,629
Suite
$2,089
From
US$1,439
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 23 January 2028
Visit: Puerto Rico, Saint Vincent, Grenada, Martinique, Antigua and Barbuda, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$722
Oceanview
$772
Balcony
$1,442
Suite
$1,652
From
US$722
Save 422
Per Person
View Trip
8 Day Southern Caribbean Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Constellation
Departure: 06 February 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Lucia, Grenada
Exclusive Savings
Inside
$704
Oceanview
$774
Balcony
$999
Suite
$3,695
From
US$704
Save 467
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Bonaire, Curacao, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$723
Oceanview
$773
Balcony
$1,243
Suite
$1,433
From
US$723
Save 632
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts with Princess
Cruise
 (8)

8 Days (7 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, Grenada, Barbados
Princess Standard
Inside
$704
Oceanview
$774
Balcony
$1,074
Suite
$1,499
From
US$704
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 24 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$1,052
Oceanview
$1,122
Balcony
$1,902
Suite
$2,162
From
US$1,052
Save 546
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (8)

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
$634
Oceanview
$734
Balcony
$1,134
Suite
$1,399
From
US$634
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Saint Vincent
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,600
Balcony
$5,300
Suite
$9,600
From
US$4,600
Save 2,500
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
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,240
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 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 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
$904
Oceanview
$1,040
Balcony
$1,424
Suite
$1,659
From
US$904
Per Person
View Trip
10 Day Southern Caribbean Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 29 October 2027
Visit: Puerto Rico, Antigua and Barbuda, Saint Lucia, Grenada, Barbados, Saint Vincent, Virgin Islands
Exclusive Savings
Inside
$868
Oceanview
$910
Balcony
$1,131
Suite
$3,235
From
US$868
Save 554
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: 01 August 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Saint Kitts and Nevis, Antigua and Barbuda
Exclusive Savings
Inside
$1,149
Oceanview
$1,460
Balcony
$1,552
Suite
$1,609
From
US$1,149
Save 634
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (8)

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
$1,391
Oceanview
$1,591
Balcony
$2,201
Suite
$2,872
From
US$1,391
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
$724
Oceanview
$739
Balcony
$1,194
Suite
$1,879
From
US$724
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
$1,209
Oceanview
$1,409
Balcony
$1,659
Suite
$2,559
From
US$1,209
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
Bonus Onboard Credit
Exclusive Savings
Inside
$584
Oceanview
$670
Balcony
$1,304
Suite
$1,529
From
US$584
Save 348
Per Person
View Trip
8 Day Southern Caribbean with Barbados Holiday with Princess
Cruise
 (8)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Princess Standard
Inside
$1,374
Oceanview
$1,464
Balcony
$2,176
Suite
$2,449
From
US$1,374
Per Person
View Trip
19 Day Caribbean Holiday Cruise: San Juan, St. Barts & Curacao with Azamara Cruises
Cruise
 (3)

19 Days (18 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 18 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+8 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis
Azamara Always Included
Inside
$5,689
Oceanview
$5,999
Balcony
$7,439
Suite
$11,799
From
US$5,689
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: 12 February 2028
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Lucia, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$833
Oceanview
$973
Balcony
$1,323
Suite
$3,850
From
US$833
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
Limited Time Offer
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$3,983
From
US$1,043
Per Person
View Trip
14 Day Caribbean Cruise: San Juan, Antigua & St. Lucia with Azamara Cruises
Cruise
 (3)

14 Days (13 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 05 December 2026
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
$3,399
Oceanview
$3,749
Balcony
$4,669
Suite
$7,399
From
US$3,399
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 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
Limited Time Offer
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$3,983
From
US$1,043
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
Departures: Nov 2026 to Jan 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Martinique, Saint Kitts and Nevis
Limited Time Offer
Inside
$977
Oceanview
$1,043
Balcony
$1,253
Suite
$3,913
From
US$977
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: 02 May 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Dominica
Exclusive Savings
Inside
$989
Oceanview
$1,003
Balcony
-
Suite
-
From
US$989
Save 560
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: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
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
$1,419
Balcony
$1,509
Suite
$2,089
From
US$1,259
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
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,553
Oceanview
$1,804
Balcony
$2,723
Suite
$2,561
From
US$1,553
Save 806
Per Person
View Trip
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