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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)
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
Save 100
Per Person
View Trip
8 Day Antiguan Elegance & Sunny St. Isles 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
Black Friday Sale
Inside
$973
Oceanview
$1,113
Balcony
$1,323
Suite
$4,305
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
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
8 Day Southern Caribbean with Barbados and St. Lucia Holiday with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand 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
6 Day Beaches of the Virgin Islands with Emerald Cruises
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
8 Day Valiant Caribbean Holidays 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
Black Friday Sale
Inside
$1,323
Oceanview
$1,533
Balcony
$1,736
Suite
$4,830
From
US$1,323
Per Person
View Trip
22 Day From the Caribbean to the Amazon with Viking Cruises
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
8 Day Southern Caribbean with Barbados and St. Kitts with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand 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
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand 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
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand 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
15 Day An Extended Journey of Tropical Harmony & Natural Wonders with Explora Journeys
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
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
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
8 Day Valiant New Year's Ahoy! with Virgin Voyages
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
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: 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
11 Day San Juan to San Juan with Silversea
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
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
Exclusive Savings
Inside
$3,365
Oceanview
$4,121
Balcony
$5,275
Suite
$7,856
From
US$3,365
Save 81
Per Person
View Trip
7 Day Caribbean East: Virgin & Saint Isles with Virgin Voyages
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
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (6)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown 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
8 Day Colorful Curacao, Aruba & Antigua with Virgin Voyages
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
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand 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
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
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$7,150
Suite
$8,710
From
US$7,150
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 Shadow
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
8 Day Southern Caribbean with Barbados and Antigua Holiday with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand 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
8 Day Southern Caribbean Cruise San Juan To San Juan with Norwegian Cruise Line
Cruise

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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$3,463
From
US$3,463
Save 96
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: 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
8 Day Sunsets in the Lesser Antilles with Virgin Voyages
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
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
New ReleaseCruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
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
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, 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
8 Day Southern Caribbean From San Juan To San Juan with Norwegian Cruise Line
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
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
8 Day Antigua & the St. Isles with Virgin Voyages
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
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