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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)
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: 20 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,798
Oceanview
$2,098
Balcony
$2,768
Suite
$3,278
From
US$1,798
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
$7,525
From
US$7,525
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 06 February 2027
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, 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 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 with Barbados and St. Kitts with Princess
Cruise
 (9)

8 Days (7 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, Grenada, Barbados
Princess Standard
Inside
$779
Oceanview
$889
Balcony
$1,224
Suite
$1,619
From
US$779
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
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 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 Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Constellation
Departure: 20 March 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Lucia, Barbados
Exclusive Savings
Inside
$994
Oceanview
$993
Balcony
$1,217
Suite
$3,178
From
US$993
Save 635
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
Inside
$3,579
Oceanview
$4,369
Balcony
$5,559
Suite
$8,619
From
US$3,579
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
$1,763
From
US$884
Save 482
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Martin
Exclusive Savings
Inside
$1,474
Oceanview
$1,754
Balcony
$2,626
Suite
$2,511
From
US$1,474
Save 771
Per Person
View Trip
8 Day A Journey Of Sun-hazed Island Enchantment & Caribbean Treasures with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 January 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Turks and Caicos Islands, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,160
From
US$5,160
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 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados, Saint Kitts and Nevis, Saint Martin
Inside
$1,539
Oceanview
$1,659
Balcony
$2,249
Suite
$2,619
From
US$1,539
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
$715
Oceanview
$633
Balcony
$1,257
Suite
$1,323
From
US$633
Save 510
Per Person
View Trip
8 Day Southern Caribbean Cruise New Year’s with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 26 December 2027
Visit: Puerto Rico, Saint Martin, Barbados, Martinique, Antigua and Barbuda, Virgin Islands
Limited Time Offer
Inside
$1,673
Oceanview
$1,813
Balcony
$2,093
Suite
$4,480
From
US$1,673
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: 14 November 2026
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Saint Kitts and Nevis, Virgin Islands
Exclusive Savings
Inside
$713
Oceanview
$794
Balcony
$1,306
Suite
$1,459
From
US$713
Save 450
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
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: 22 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
8 Day A Journey of Intimate Island Bliss & Caribbean Breeze with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 February 2028
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
Per Person
View Trip
10 Day Southern Caribbean Cruise: St.barts, Antigua & Tortola with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 05 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, USA
Azamara Always Included
Inside
$2,919
Oceanview
$3,449
Balcony
$4,119
Suite
$6,349
From
US$2,919
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: 12 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique, Dominica, Barbados
Princess Standard
Inside
$649
Oceanview
$849
Balcony
$1,024
Suite
$1,399
From
US$649
Per Person
View Trip
6 Day Eastern Caribbean: San Juan to Miami with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) San Juan to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 April 2027
Visit: Puerto Rico, Dominican Republic, Bahamas, USA
Limited Time Offer
Inside
$681
Oceanview
$735
Balcony
$897
Suite
$2,600
From
US$681
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
9 Day Southern Caribbean Holiday Cruise: British Virgin Islands, Dominica & Grenada with Azamara Cruises
Cruise
 (5)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,189
Oceanview
$2,749
Balcony
$3,349
Suite
$5,109
From
US$2,189
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: 16 April 2028
Visit: Puerto Rico, Virgin Islands, Curacao, Bonaire, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$903
Oceanview
$964
Balcony
$1,734
Suite
$1,943
From
US$903
Save 491
Per Person
View Trip
8 Day A Journey Of Caribbean Delicacies & Idyllic Islands with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 04 January 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Montserrat, Virgin Islands, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$4,025
From
US$4,025
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: 16 January 2028
Visit: Puerto Rico, Aruba, Barbados, Saint Martin, Saint Kitts and Nevis
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
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: 13 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Martinique, Grenada
Princess Standard
Inside
$1,818
Oceanview
$2,108
Balcony
$2,788
Suite
$3,618
From
US$1,818
Per Person
View Trip
Results: 31-60 of 235

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