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Cruises from San Juan

Choose from 235 unique cruises starting in San Juan, and traveling to Barcelona, Bridgetown, Colon, Fort Lauderdale, Lisbon and more. December is the most popular month to join a cruise from San Juan and you can select from 396 departures available from twelve leading cruise lines.
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235 Cruises (396 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
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: 28 November 2027
Visit: Puerto Rico, Aruba, Curacao, Saint Martin, Saint Kitts and Nevis
Inside
$1,129
Oceanview
$1,279
Balcony
$1,499
Suite
$2,299
From
US$1,129
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: 28 February 2027
Visit: Puerto Rico, Virgin Islands, Dominica, Barbados, Saint Martin
Inside
$1,519
Oceanview
$1,579
Balcony
$1,719
Suite
$2,009
From
US$1,519
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 Viva
Departure: 23 January 2028
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Bonaire, Curacao
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
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
Inside
$929
Oceanview
$1,079
Balcony
$1,474
Suite
$1,759
From
US$929
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
$1,738
Oceanview
$1,978
Balcony
$2,688
Suite
$3,348
From
US$1,738
Per Person
View Trip
15 Day Southern Caribbean Adventurer Holiday with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 12 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Dominica, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,498
Oceanview
$1,998
Balcony
$2,498
Suite
$3,248
From
US$1,498
Per Person
View Trip
21 Day Mediterranean & Atlantic Crossing with Viking Cruises
Cruise
 (5)

21 Days (20 Nights) San Juan to Rome
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 06 March 2027
Visit: Puerto Rico, Saint Martin, Portugal, Spain, France, Monaco, Italy
Viking $1,299 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,398
Suite
$11,798
From
US$7,398
Per Person
View Trip
8 Day A Journey Through Beguiling Tropical Elegance To Vibrant Island Delights with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 27 February 2028
Visit: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
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
Departures: Nov 2026 to Jan 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Martinique, Saint Kitts and Nevis
Limited Time Offer
Inside
$1,043
Oceanview
$1,043
Balcony
$1,323
Suite
$2,863
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
15 Day Southern Caribbean Adventurer Holiday with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$2,008
Oceanview
$2,408
Balcony
$3,148
Suite
$4,118
From
US$2,008
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: 20 November 2026
Visit: Puerto Rico, Virgin Islands, Curacao, Aruba, Saint Kitts and Nevis, Saint Martin
Limited Time Offer
Inside
$1,272
Oceanview
$1,592
Balcony
$1,752
Suite
$4,552
From
US$1,272
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
Inside
-
Oceanview
-
Balcony
$11,999
Suite
-
From
US$11,999
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,410
Oceanview
$1,601
Balcony
$2,720
Suite
$3,000
From
US$1,410
Save 701
Per Person
View Trip
15 Day San Juan to Lisbon with Silversea
Cruise

15 Days (14 Nights) San Juan to Lisbon
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 09 March 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Spain, Portugal
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,700
Balcony
$5,000
Suite
$8,600
From
US$4,700
Save 2,500
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (9)

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
$1,506
Oceanview
$1,636
Balcony
$2,726
Suite
$3,676
From
US$1,506
Per Person
View Trip
8 Day A Journey Through Balmy Shores & Stirring Scenery with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 April 2027
Visit: Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,920
From
US$3,920
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
$1,770
Oceanview
$1,883
Balcony
$2,163
Suite
$4,473
From
US$1,770
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: Dec 2027 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$732
Oceanview
$792
Balcony
$1,332
Suite
$1,462
From
US$732
Save 435
Per Person
View Trip
18 Day Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba with Azamara Cruises
Cruise
 (5)

18 Days (17 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+10 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Bonaire, Curacao, Aruba, Dominican Republic, Bahamas, USA
Azamara Always Included
Inside
$4,729
Oceanview
$5,809
Balcony
$7,139
Suite
$10,859
From
US$4,729
Per Person
View Trip
8 Day Southern Caribbean with Aruba with Princess
Cruise
 (9)

8 Days (7 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Crown Princess
Departure: 28 March 2027
Visit: Puerto Rico, Saint Martin, Aruba, Curacao, USA
Princess Standard
Inside
$769
Oceanview
$859
Balcony
$974
Suite
$1,299
From
US$769
Per Person
View Trip
16 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (5)

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 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
$4,089
Oceanview
$5,099
Balcony
$6,289
Suite
$9,529
From
US$4,089
Per Person
View Trip
8 Day A Journey to Island Rhythms & Tranquil Bahamian Bliss with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Jan 2028 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
11 Day Caribbean Mystique with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 30 March 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+5 more), Saint Barthelemy, Saint Martin, Dominican Republic, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,099
Suite
$10,499
From
US$10,099
Save 10,099
Per Person
View Trip
8 Day A Journey Through A Caribbean Tapestry Of Serenity & Splendour with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Turks and Caicos Islands, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$3,850
From
US$3,850
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 February 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Kitts and Nevis, Saint Martin
Inside
$1,349
Oceanview
$1,509
Balcony
$1,749
Suite
$2,519
From
US$1,349
Per Person
View Trip
9 Day San Juan to Miami, Fl with Silversea
Cruise
 (1)

9 Days (8 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 29 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Antigua and Barbuda, USA
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,900
Suite
$9,200
From
US$6,900
Save 1,500
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: 20 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Lucia, Barbados, Dominica, Saint Martin
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: 14 March 2027
Visit: Puerto Rico, Virgin Islands, Curacao, Aruba
Inside
$1,389
Oceanview
$1,419
Balcony
$1,689
Suite
$2,309
From
US$1,389
Per Person
View Trip
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