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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 316 departures available from ten of the world's leading cruise lines.
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167 Cruises (316 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 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
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
$1,419
Oceanview
$1,479
Balcony
$1,599
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
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: 31 January 2027
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$1,477
Oceanview
$1,557
Balcony
$2,442
Suite
$3,112
From
US$1,477
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
$1,489
Oceanview
$1,609
Balcony
$1,709
Suite
$1,959
From
US$1,489
Per Person
View Trip
9 Day Southern Caribbean & Aruban Holidays with Virgin Voyages
Cruise
 (1)

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
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: 24 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Guadeloupe, Dominica, Grenada
Princess Standard
Inside
$1,427
Oceanview
$1,397
Balcony
$2,462
Suite
$3,262
From
US$1,397
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
$2,389
From
US$1,259
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
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
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 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
$1,949
From
US$1,489
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
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: 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
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: 28 November 2027
Visit: Puerto Rico, Aruba, Curacao, Saint Martin, Saint Kitts and Nevis
Inside
$1,129
Oceanview
$1,279
Balcony
$1,499
Suite
$2,299
From
US$1,129
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
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
-
Oceanview
$5,749
Balcony
$7,299
Suite
$11,299
From
US$5,749
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
$714
Oceanview
$664
Balcony
$1,124
Suite
$1,349
From
US$664
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 Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,113
Oceanview
$1,323
Balcony
$1,603
Suite
$4,123
From
US$1,113
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
$590
Oceanview
$619
Balcony
$1,103
Suite
$1,316
From
US$590
Save 445
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: 20 November 2026
Visit: Puerto Rico, Virgin Islands, Curacao, Aruba, Saint Kitts and Nevis, Saint Martin
Inside
$1,272
Oceanview
$1,512
Balcony
$1,717
Suite
$4,552
From
US$1,272
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
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
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
$1,079
Oceanview
$1,149
Balcony
$2,022
Suite
$2,417
From
US$1,079
Save 558
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
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
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
Inside
$833
Oceanview
$973
Balcony
$1,323
Suite
$3,850
From
US$833
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts 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 Jan 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$764
Oceanview
$884
Balcony
$1,274
Suite
$1,599
From
US$764
Per Person
View Trip
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