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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)
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
Inside
-
Oceanview
-
Balcony
$3,799
Suite
$5,999
From
US$3,799
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 21 November 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
$3,799
Oceanview
$4,809
Balcony
$5,859
Suite
$8,929
From
US$3,799
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 Summit
Departure: 14 November 2027
Visit: Puerto Rico, Saint Vincent, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$594
Oceanview
$664
Balcony
$808
Suite
$2,572
From
US$594
Save 393
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: 27 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$6,501
Balcony
-
Suite
$8,139
From
US$6,501
Save 644
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: 28 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$1,113
Oceanview
$1,183
Balcony
$1,393
Suite
$3,983
From
US$1,113
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: 03 January 2027
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao
Inside
$1,719
Oceanview
$1,779
Balcony
$1,889
Suite
$2,069
From
US$1,719
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
Ship: Crown Princess
Departure: 17 January 2027
Visit: Puerto Rico, Saint Martin, Martinique, Grenada, Saint Lucia, Barbados
Princess Standard
Inside
$774
Oceanview
$824
Balcony
$1,324
Suite
$1,849
From
US$774
Per Person
View Trip
15 Day An Extended Journey Through Golden Shores & Island Grace with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy (+4 more), Turks and Caicos Islands, USA, Antigua and Barbuda, Guadeloupe
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,140
From
US$7,140
Per Person
View Trip
8 Day Sisters at Sea: Valiant Lady with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 13 February 2027
Visit: Puerto Rico, Dominican Republic, Turks and Caicos Islands
Limited Time Offer
Inside
$1,183
Oceanview
$1,393
Balcony
$1,670
Suite
$4,123
From
US$1,183
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
Departures: Nov 2027 to Dec 2027
Visit: Puerto Rico, Aruba, Barbados, Saint Lucia, Saint Kitts and Nevis
Inside
$1,419
Oceanview
$1,619
Balcony
$1,869
Suite
$2,769
From
US$1,419
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
Limited Time Offer
Inside
$1,112
Oceanview
$1,272
Balcony
$1,592
Suite
$4,960
From
US$1,112
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: 28 February 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique, Saint Vincent, Grenada
Bonus Onboard Credit
Exclusive Savings
Inside
$726
Oceanview
$856
Balcony
$2,069
Suite
$2,228
From
US$726
Save 416
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
Cruise Line: Princess
Ship: Emerald Princess
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$1,593
Oceanview
$1,738
Balcony
$2,143
Suite
$3,058
From
US$1,593
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 05 April 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$1,101
Oceanview
-
Balcony
-
Suite
-
From
US$1,655
Save 50
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 Summit
Departure: 12 December 2027
Visit: Puerto Rico, Saint Vincent, Barbados, Martinique, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$618
Oceanview
$619
Balcony
$893
Suite
$2,933
From
US$618
Save 408
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: Valiant Lady
Departure: 19 March 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Dominica, Saint Martin
Limited Time Offer
Inside
$1,192
Oceanview
$1,432
Balcony
$1,672
Suite
$4,552
From
US$1,192
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
$835
Oceanview
$736
Balcony
$1,217
Suite
$1,312
From
US$736
Save 510
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
Limited Time Offer
Inside
$903
Oceanview
$1,043
Balcony
$1,253
Suite
$3,850
From
US$903
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: 17 January 2027
Visit: Puerto Rico, Saint Martin, Martinique, Grenada (+4 more), Saint Lucia, Barbados, Virgin Islands, Antigua and Barbuda
Princess Standard
Inside
$1,351
Oceanview
$1,501
Balcony
$2,441
Suite
$3,346
From
US$1,351
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
Inside
$1,339
Oceanview
$1,439
Balcony
$1,689
Suite
$2,419
From
US$1,339
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: 06 March 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
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 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 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
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: 05 December 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Barbados, Aruba
Inside
$1,119
Oceanview
$1,319
Balcony
$1,569
Suite
$2,469
From
US$1,119
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (1)

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
Limited Time Offer
Inside
$973
Oceanview
$1,183
Balcony
$1,463
Suite
$4,053
From
US$973
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: 14 November 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Curacao, Aruba
Inside
$1,269
Oceanview
$1,469
Balcony
$1,719
Suite
$2,619
From
US$1,269
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
Inside
$2,059
Oceanview
$2,309
Balcony
$2,609
Suite
$3,759
From
US$2,059
Per Person
View Trip
8 Day Southern Caribbean New Year's Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 26 December 2026
Visit: Puerto Rico, Saint Martin, Martinique, Barbados, Saint Lucia, Antigua and Barbuda
Limited Time Offer
Inside
$1,813
Oceanview
$1,883
Balcony
$2,163
Suite
$4,473
From
US$1,813
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
$1,663
Oceanview
$1,901
Balcony
$2,613
Suite
$3,168
From
US$1,663
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: 02 April 2028
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Vincent, Grenada, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$884
Oceanview
$943
Balcony
$1,534
Suite
$1,813
From
US$884
Save 482
Per Person
View Trip
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