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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)
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
$1,714
Oceanview
$1,979
Balcony
$2,634
Suite
$3,119
From
US$1,714
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
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
$1,391
Oceanview
$1,491
Balcony
$2,381
Suite
$3,106
From
US$1,391
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 Jan 2028
Visit: Puerto Rico, Barbados, Grenada, Saint Vincent, Antigua and Barbuda, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$729
Oceanview
$780
Balcony
$1,509
Suite
$1,710
From
US$729
Save 477
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
$1,983
Oceanview
$2,241
Balcony
$3,013
Suite
$3,698
From
US$1,983
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: Valiant Lady
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Limited Time Offer
Inside
$834
Oceanview
$1,014
Balcony
$1,194
Suite
$3,414
From
US$834
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: 26 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,389
Oceanview
$1,589
Balcony
$2,699
Suite
$2,812
From
US$1,389
Save 736
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, St. Lucia & St. Kitts with Azamara Cruises
Cruise
 (3)

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
$3,579
Oceanview
$4,369
Balcony
$5,559
Suite
$8,619
From
US$3,579
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 San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 28 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Kitts and Nevis
All-Inclusive Fare
Inside
-
Oceanview
$5,600
Balcony
$6,100
Suite
$10,700
From
US$5,600
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
Limited Time Offer
Inside
$973
Oceanview
$1,183
Balcony
$1,463
Suite
$3,983
From
US$973
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
$1,410
Oceanview
$1,601
Balcony
$2,720
Suite
$3,050
From
US$1,410
Save 701
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
Departures: Dec 2026 to Apr 2027
Visit: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Limited Time Offer
Inside
$973
Oceanview
$1,183
Balcony
$1,393
Suite
$3,703
From
US$973
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: Feb 2028 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$779
Oceanview
$840
Balcony
$1,499
Suite
$1,679
From
US$779
Save 495
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: 16 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Barbados, Saint Lucia, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$1,633
Oceanview
$1,856
Balcony
$2,593
Suite
$3,158
From
US$1,633
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: 12 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Dominica, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,813
Oceanview
$2,012
Balcony
$2,943
Suite
$3,978
From
US$1,813
Per Person
View Trip
8 Day Southern Caribbean Holiday Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Martinique, Aruba, Curacao
Limited Time Offer
Inside
$1,113
Oceanview
$1,253
Balcony
$1,463
Suite
$4,123
From
US$1,113
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Antigua with Princess
Cruise
 (8)

8 Days (7 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, Dominica, Barbados
Princess Standard
Inside
$714
Oceanview
$714
Balcony
$1,304
Suite
$1,629
From
US$714
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
$854
Oceanview
$959
Balcony
$1,404
Suite
$1,679
From
US$854
Per Person
View Trip
17 Day An Extended Journey of Island Energy & Ocean Tranquillity with Explora Journeys
Cruise

17 Days (16 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 January 2027
Visit: Puerto Rico, Saint Martin, Guadeloupe, Grenada (+7 more), Saint Lucia, Dominican Republic, USA, Virgin Islands, Anguilla, Martinique, Saint Kitts and Nevis
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$9,720
From
US$9,720
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
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 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
$1,299
Oceanview
$1,409
Balcony
$1,649
Suite
$2,409
From
US$1,299
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 Epic
Departure: 05 April 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados, Saint Lucia, Sint Maarten
Inside
$949
Oceanview
-
Balcony
$1,219
Suite
$1,839
From
US$949
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 Epic
Departure: 12 April 2026
Visit: Puerto Rico, Aruba, Curacao, Bonaire, Saint Lucia, Saint Kitts and Nevis
Inside
$779
Oceanview
-
Balcony
-
Suite
$1,229
From
US$779
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
$1,439
Balcony
$1,539
Suite
$2,049
From
US$1,359
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: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Inside
$1,209
Oceanview
$1,409
Balcony
$1,659
Suite
$2,559
From
US$1,209
Per Person
View Trip
8 Day West Indies Island Hopping with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 20 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$6,186
Balcony
-
Suite
$7,824
From
US$6,186
Save 609
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
$1,499
Balcony
$1,729
Suite
$1,959
From
US$1,359
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
$1,119
Oceanview
$1,319
Balcony
$1,569
Suite
$2,469
From
US$1,119
Per Person
View Trip
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