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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 317 departures available from ten of the world's leading cruise lines.
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168 Cruises (317 Departures)
168 Cruises (317 Departures)
Departures
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Duration
6 Days
25 Days
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Price
$800pp
$28,080pp
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15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (6)

15 Days (14 Nights) San Juan to San Juan
Operator: Azamara
Ship: Azamara Quest
Departure: 21 November 2027
Visits: 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
Exclusive Savings
Inside
$5,056
Oceanview
$6,388
Balcony
$7,756
Suite
$11,778
From (Per Person)
A$5,056
Save 343
Per Person
View Trip
8 Day Southern Caribbean New Year's Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 26 December 2026
Visits: Puerto Rico, Saint Martin, Martinique, Barbados, Saint Lucia, Antigua and Barbuda
Drinks On Us
Inside
$2,184
Oceanview
$2,284
Balcony
$2,384
Suite
$6,873
From (Per Person)
A$2,184
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 11 December 2027
Visits: Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Lucia, Aruba
Drinks On Us
Inside
$1,187
Oceanview
$1,685
Balcony
$1,985
Suite
$5,279
From (Per Person)
A$1,187
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 15 January 2028
Visits: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Antigua and Barbuda, Saint Martin
Drinks On Us
Inside
$1,088
Oceanview
$1,686
Balcony
$1,885
Suite
$5,280
From (Per Person)
A$1,088
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 13 December 2026
Visits: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Barbados, Saint Lucia, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$1,571
Oceanview
$1,616
Balcony
$1,854
Suite
$3,356
From (Per Person)
A$1,571
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts with Princess
Cruise
 (12)

8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Jan 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$1,090
Oceanview
$1,193
Balcony
$1,625
Suite
$2,278
From (Per Person)
A$1,090
Per Person
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departures: Jan 2028 to Mar 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda +5 more, Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Exclusive Savings
Inside
$2,260
Oceanview
$2,787
Balcony
$3,022
Suite
$4,220
From (Per Person)
A$2,260
Per Person
View Trip
9 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

9 Days (8 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 29 January 2027
Visits: Puerto Rico, Aruba, Curacao, Bonaire, Martinique, Saint Martin
Drinks On Us
Inside
$2,042
Oceanview
$2,155
Balcony
$2,269
Suite
$6,486
From (Per Person)
A$2,042
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia Holiday with Princess
Cruise
 (12)

8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ships: Crown Princess, Emerald Princess
Departures: Dec 2026 to Dec 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,160
Oceanview
$1,373
Balcony
$1,783
Suite
$2,843
From (Per Person)
A$1,160
Save 22
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 15 April 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda, Saint Martin
Drinks On Us
Inside
$1,386
Oceanview
$1,885
Balcony
$2,084
Suite
$5,301
From (Per Person)
A$1,386
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
Operator: Princess
Ship: Emerald Princess
Departure: 16 January 2028
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Barbados, Saint Lucia
Exclusive Savings
Inside
$1,160
Oceanview
$1,290
Balcony
$1,526
Suite
$2,546
From (Per Person)
A$1,160
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Thomas with Princess
Cruise
 (12)

8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 31 January 2027
Visits: Puerto Rico, Virgin Islands, Guadeloupe, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$892
Oceanview
$1,027
Balcony
$1,902
Suite
$2,337
From (Per Person)
A$892
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
Operator: Princess
Ship: Emerald Princess
Departures: Nov 2027 to Mar 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$1,159
Oceanview
$1,318
Balcony
$1,506
Suite
$2,179
From (Per Person)
A$1,159
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 13 February 2028
Visits: Puerto Rico, Virgin Islands, Saint Martin, Dominica +5 more, Saint Lucia, Barbados, Saint Kitts and Nevis, Martinique, Grenada
Exclusive Savings
Inside
$2,497
Oceanview
$3,313
Balcony
$3,646
Suite
$5,850
From (Per Person)
A$2,497
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (12)

15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 24 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda +5 more, Saint Lucia, Barbados, Guadeloupe, Dominica, Grenada
Exclusive Savings
Inside
$1,864
Oceanview
$2,238
Balcony
$4,596
Suite
$6,566
From (Per Person)
A$1,864
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Dec 2026 to Feb 2027
Visits: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Barbados, Saint Lucia, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,345
Oceanview
$2,568
Balcony
$3,164
Suite
$3,759
From (Per Person)
A$2,345
Per Person
View Trip
9 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

9 Days (8 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 20 November 2026
Visits: Puerto Rico, Virgin Islands, Curacao, Aruba, Saint Kitts and Nevis, Saint Martin
Drinks On Us
Inside
$1,583
Oceanview
$1,699
Balcony
$1,812
Suite
$5,802
From (Per Person)
A$1,583
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 14 November 2026
Visits: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Saint Kitts and Nevis, Virgin Islands
Exclusive Savings
Inside
$1,092
Oceanview
$1,121
Balcony
$2,028
Suite
$2,657
From (Per Person)
A$1,092
Save 668
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 07 March 2027
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$2,301
Oceanview
$2,375
Balcony
$2,925
Suite
$3,194
From (Per Person)
A$2,301
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2027 to Mar 2027
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Drinks On Us
Inside
$1,273
Oceanview
$1,359
Balcony
$1,444
Suite
$4,437
From (Per Person)
A$1,273
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 20 February 2027
Visits: Puerto Rico, Virgin Islands, Saint Lucia, Barbados, Dominica, Saint Martin
Drinks On Us
Inside
$1,587
Oceanview
$1,686
Balcony
$1,786
Suite
$5,376
From (Per Person)
A$1,587
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 21 November 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Dominica +4 more, Saint Lucia, Barbados, Saint Kitts and Nevis, Grenada
Exclusive Savings
Inside
$2,517
Oceanview
$3,147
Balcony
$3,438
Suite
$4,953
From (Per Person)
A$2,517
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Jan 2028
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$2,077
Oceanview
$2,345
Balcony
$2,703
Suite
$4,012
From (Per Person)
A$2,077
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departures: Nov 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Barbados, Saint Lucia, Dominica, Saint Martin
Drinks On Us
Inside
$1,287
Oceanview
$1,786
Balcony
$1,985
Suite
$5,280
From (Per Person)
A$1,287
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departures: Nov 2026 to Jan 2027
Visits: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Martinique, Saint Kitts and Nevis
Drinks On Us
Inside
$1,386
Oceanview
$1,486
Balcony
$1,586
Suite
$3,780
From (Per Person)
A$1,386
Per Person
View Trip
9 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

9 Days (8 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 19 March 2027
Visits: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Dominica, Saint Martin
Drinks On Us
Inside
$1,357
Oceanview
$1,471
Balcony
$1,813
Suite
$6,144
From (Per Person)
A$1,357
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 24 December 2027
Visits: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,664
Oceanview
$1,760
Balcony
$2,953
Suite
$3,715
From (Per Person)
A$1,664
Save 912
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 20 February 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique +5 more, Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$2,705
Oceanview
$3,036
Balcony
$3,567
Suite
$4,755
From (Per Person)
A$2,705
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departures: Jan 2028 to Mar 2028
Visits: Puerto Rico, Aruba, Saint Lucia, Antigua and Barbuda, Saint Martin
Drinks On Us
Inside
$1,088
Oceanview
$1,685
Balcony
$1,886
Suite
$5,280
From (Per Person)
A$1,088
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 14 March 2027
Visits: Puerto Rico, Virgin Islands, Curacao, Aruba
Just Cruise Fare
Exclusive Savings
Inside
$2,330
Oceanview
$2,301
Balcony
$2,628
Suite
$3,298
From (Per Person)
A$2,301
Per Person
View Trip
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