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Cruises Starting and Ending in San Juan

Are you looking for a cruise starting and ending in San Juan? January is the most popular month to join a roundtrip cruise from San Juan and we have 265 departures available from eleven of the world's leading cruise lines.
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153 Cruises (265 Cruise Departures)
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
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 100
Per Person
View Trip
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
Black Friday Sale
Inside
$973
Oceanview
$1,113
Balcony
$1,323
Suite
$4,305
From
US$973
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departure: 30 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$736
Oceanview
$797
Balcony
$1,447
Suite
$1,691
From
US$736
Save 414
Per Person
View Trip
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 23 November 2025
Visit: Puerto Rico, Saint Martin, Saint Lucia, Barbados, Grenada, Dominica
Princess Standard
Inside
$406
Oceanview
$497
Balcony
$725
Suite
$1,580
From
US$406
Per Person
View Trip
New ReleaseCruise

6 Days (5 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Jan 2028 to Feb 2028
Visit: Puerto Rico, Virgin Islands
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$4,919
Balcony
-
Suite
$6,180
From
US$4,919
Save 5,271
Per Person
View Trip
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
Black Friday Sale
Inside
$1,323
Oceanview
$1,533
Balcony
$1,736
Suite
$4,830
From
US$1,323
Per Person
View Trip
Cruise
 (5)

22 Days (21 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 15 December 2026
Visit: Puerto Rico, Barbados, French Guiana, Brazil (+4 more), Trinidad and Tobago, Saint Lucia, Antigua and Barbuda, Virgin Islands
Viking $799 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,799
Suite
$17,999
From
US$10,799
Save 200
Per Person
View Trip
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 01 February 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Dominica, Barbados
Princess Standard
Inside
$772
Oceanview
$642
Balcony
$1,297
Suite
$1,372
From
US$642
Per Person
View Trip
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 15 March 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$1,149
Oceanview
$1,282
Balcony
-
Suite
-
From
US$1,149
Per Person
View Trip
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 07 December 2025
Visit: Puerto Rico, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis
Princess Standard
Inside
-
Oceanview
$679
Balcony
$949
Suite
$999
From
US$679
Per Person
View Trip
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands (+4 more), Dominican Republic, USA, Guadeloupe, Saint Martin
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$7,150
Suite
$8,710
From
US$7,150
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departure: 17 January 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Martinique, Barbados
Exclusive Savings
Inside
$709
Oceanview
$749
Balcony
$889
Suite
$2,144
From
US$709
Save 400
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 27 December 2025
Visit: Puerto Rico, Sint Maarten, Saint Kitts and Nevis, Saint Lucia, Barbados, Virgin Islands
Black Friday Sale
Inside
$1,673
Oceanview
$1,743
Balcony
$1,936
Suite
$4,760
From
US$1,673
Per Person
View Trip
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departure: 01 March 2026
Visit: Puerto Rico, Curacao, Aruba, Virgin Islands
Exclusive Savings
Inside
$759
Oceanview
$859
Balcony
$1,033
Suite
$3,151
From
US$759
Save 445
Per Person
View Trip
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departures: Jan 2028 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,230
Balcony
$4,860
Suite
$9,900
From
US$4,230
Save 480
Per Person
View Trip
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
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
Exclusive Savings
Inside
$3,365
Oceanview
$4,121
Balcony
$5,275
Suite
$7,856
From
US$3,365
Save 81
Per Person
View Trip
Cruise
 (1)

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
Black Friday Sale
Inside
$865
Oceanview
$894
Balcony
$1,074
Suite
$3,690
From
US$865
Per Person
View Trip
Cruise
 (6)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 31 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$2,046
Oceanview
$2,516
Balcony
$3,081
Suite
$3,588
From
US$2,046
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 27 March 2027
Visit: Puerto Rico, Curacao, Aruba, Antigua and Barbuda, Saint Martin
Black Friday Sale
Inside
-
Oceanview
-
Balcony
$1,508
Suite
-
From
US$1,508
Per Person
View Trip
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 01 March 2026
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Grenada, Barbados, Virgin Islands
Princess Standard
Inside
$1,094
Oceanview
$1,422
Balcony
-
Suite
$2,422
From
US$1,094
Per Person
View Trip
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
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$7,150
Suite
$8,710
From
US$7,150
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Saint Vincent
All-Inclusive Fare
Inside
-
Oceanview
$6,400
Balcony
$7,500
Suite
$8,500
From
US$6,400
Per Person
View Trip
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 21 December 2025
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Dominica, Grenada, Barbados
Princess Standard
Inside
$562
Oceanview
$556
Balcony
$817
Suite
$1,015
From
US$556
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Departure: 14 February 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Kitts and Nevis, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$3,463
From
US$3,463
Save 96
Per Person
View Trip
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departure: 04 January 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Grenada, Aruba, Curacao
Exclusive Savings
Inside
$899
Oceanview
$919
Balcony
$979
Suite
$2,041
From
US$899
Save 505
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Mar 2026 to Apr 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Martinique, Curacao, Aruba
Black Friday Sale
Inside
$903
Oceanview
$1,043
Balcony
$1,253
Suite
$3,570
From
US$903
Per Person
View Trip
New ReleaseCruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Departure: 17 January 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Montserrat, Antigua and Barbuda, Guadeloupe
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$34,338
From
US$34,338
Save 28,942
Per Person
View Trip
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, Dominica, Antigua and Barbuda, Saint Kitts and Nevis
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,410
From
US$3,850
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Departures: Dec 2026 to Feb 2027
Visit: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Barbados, Saint Lucia, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$3,259
From
US$3,259
Save 136
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 January 2026
Visit: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia, Virgin Islands
Black Friday Sale
Inside
$873
Oceanview
$973
Balcony
$1,183
Suite
$3,150
From
US$873
Per Person
View Trip
Results: 1-30 of 153

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