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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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162 Cruises (317 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 Savings Event
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,434
Suite
$8,864
From
A$5,434
Save 1,391
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Antigua with Princess
Cruise
 (11)

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
Exclusive Savings
Inside
$1,112
Oceanview
$1,112
Balcony
$1,944
Suite
$2,498
From
A$1,112
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
Departures: Nov 2026 to Jan 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Martinique, Saint Kitts and Nevis
Inside
$1,588
Oceanview
$1,786
Balcony
$1,886
Suite
$4,083
From
A$1,588
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
Exclusive Deal
Exclusive Savings
Inside
$2,257
Oceanview
$2,551
Balcony
$4,085
Suite
$7,252
From
A$2,257
Save 935
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (11)

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
Exclusive Savings
Inside
$2,254
Oceanview
$2,552
Balcony
$3,789
Suite
$4,393
From
A$2,254
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

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
Inside
$1,388
Oceanview
$1,688
Balcony
$1,987
Suite
$5,281
From
A$1,388
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (11)

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
Exclusive Savings
Inside
$2,185
Oceanview
$2,256
Balcony
$3,719
Suite
$4,828
From
A$2,185
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

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
$1,088
Oceanview
$1,288
Balcony
$1,787
Suite
$5,491
From
A$1,088
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: 06 March 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Inside
$1,488
Oceanview
$1,788
Balcony
$2,087
Suite
$5,681
From
A$1,488
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
Just Cruise Fare
Exclusive Savings
Inside
$2,181
Oceanview
$2,479
Balcony
$2,851
Suite
$4,191
From
A$2,181
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
Exclusive Savings
Inside
$1,389
Oceanview
$1,528
Balcony
$2,151
Suite
$2,617
From
A$1,389
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 Deal
Exclusive Savings
Inside
$1,228
Oceanview
$1,398
Balcony
$1,871
Suite
$4,422
From
A$1,228
Save 527
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
Exclusive Deal
Exclusive Savings
Inside
$1,324
Oceanview
$1,406
Balcony
$2,226
Suite
$4,043
From
A$1,324
Save 502
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
Just Cruise Fare
Exclusive Savings
Inside
$3,149
Oceanview
$3,506
Balcony
$3,923
Suite
$5,516
From
A$3,149
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: 05 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Martinique, Dominica
Princess Standard
Exclusive Savings
Inside
$2,254
Oceanview
$2,597
Balcony
$3,403
Suite
$4,303
From
A$2,254
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
Exclusive Savings
Inside
$2,432
Oceanview
$2,874
Balcony
$3,502
Suite
$4,858
From
A$2,432
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
Just Cruise Fare
Exclusive Savings
Inside
$2,390
Oceanview
$2,375
Balcony
$2,613
Suite
$3,417
From
A$2,375
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
$1,587
Oceanview
$1,887
Balcony
$2,187
Suite
$5,880
From
A$1,587
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (11)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departures: Dec 2026 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Exclusive Savings
Inside
$2,333
Oceanview
$2,455
Balcony
$3,897
Suite
$5,650
From
A$2,333
Save 35
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
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Exclusive Savings
Inside
$1,191
Oceanview
$1,320
Balcony
$1,528
Suite
$2,151
From
A$1,191
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 18 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda
Exclusive Deal
Exclusive Savings
Inside
$1,371
Oceanview
$1,461
Balcony
$2,269
Suite
$4,141
From
A$1,371
Save 540
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: Scarlet Lady
Departure: 12 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Dominica, Saint Martin
Inside
$1,357
Oceanview
$1,586
Balcony
$2,157
Suite
$6,161
From
A$1,357
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
Exclusive Savings
Inside
$2,284
Oceanview
$2,929
Balcony
$3,769
Suite
$5,056
From
A$2,284
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

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
Inside
$1,089
Oceanview
$1,287
Balcony
$1,787
Suite
$5,491
From
A$1,089
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
Just Cruise Fare
Exclusive Savings
Inside
$2,077
Oceanview
$2,345
Balcony
$2,687
Suite
$3,894
From
A$2,077
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
Just Cruise Fare
Exclusive Savings
Inside
$2,182
Oceanview
$2,479
Balcony
$2,851
Suite
$3,834
From
A$2,182
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
Just Cruise Fare
Exclusive Savings
Inside
$2,553
Oceanview
$2,628
Balcony
$2,955
Suite
$3,477
From
A$2,553
Per Person
View Trip
8 Day Southern Caribbean Holiday Cruise with Virgin Voyages
Cruise
 (2)

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
Inside
$1,488
Oceanview
$1,687
Balcony
$1,887
Suite
$5,980
From
A$1,488
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (11)

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
Exclusive Savings
Inside
$1,043
Oceanview
$1,112
Balcony
$1,667
Suite
$2,082
From
A$1,043
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 14 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Lucia, Saint Kitts and Nevis
Inside
$1,447
Oceanview
$1,618
Balcony
$1,874
Suite
$4,698
From
A$1,447
Per Person
View Trip
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