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Cruises From San Juan

Choose from 183 unique cruises starting in San Juan, and travelling to Barcelona, Bridgetown, Fort Lauderdale, Lisbon, Los Angeles and more. December is the most popular month to join a cruise from San Juan and you can select from 420 departures available from eleven leading cruise lines.
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183 Cruises (420 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
Ship: Viking Sea
Departures: Dec 2025 to Feb 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Companion Fly Free
INSIDE
-
OCEANVIEW
-
BALCONY
$6,365
SUITE
$9,991
Save (per person) 156
From (per person) 6,365
View Trip
8 Day Southern Caribbean with Barbados with Princess
Cruise
 (3)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departures: Jan 2027 to Feb 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$864
OCEANVIEW
$983
BALCONY
$1,429
SUITE
$1,993
From (per person) 864
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 31 January 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Exclusive Deal
INSIDE
$1,710
OCEANVIEW
$1,947
BALCONY
$2,908
SUITE
$4,145
From (per person) 1,710
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 27 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+1 more), Saint Martin
Exclusive Deal
INSIDE
$1,626
OCEANVIEW
$1,849
BALCONY
$2,279
SUITE
$3,597
Save (per person) 909
From (per person) 1,626
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
Departures: Nov 2025 to Jan 2026
Countries Visited: Puerto Rico, Saint Lucia, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Virgin Islands
Exclusive DealSingle Savings
INSIDE
$1,077
OCEANVIEW
$1,195
BALCONY
$1,556
SUITE
$2,837
Save (per person) 740
From (per person) 1,077
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 04 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Saint Vincent
Exclusive Deal
INSIDE
$2,106
OCEANVIEW
$2,394
BALCONY
$3,452
SUITE
$4,244
From (per person) 2,106
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
Departures: Dec 2025 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Curacao, Aruba (+1 more), Bonaire
Exclusive DealSingle Savings
INSIDE
$1,291
OCEANVIEW
$1,412
BALCONY
$1,723
SUITE
$2,899
Save (per person) 848
From (per person) 1,291
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 20 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+1 more), Saint Kitts and Nevis
Exclusive DealSingle Savings
INSIDE
$1,562
OCEANVIEW
$1,785
BALCONY
$2,169
SUITE
$3,559
Save (per person) 895
From (per person) 1,562
View Trip
10 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 20 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Grenada (+2 more), Curacao, Aruba
Exclusive Deal
INSIDE
$1,356
OCEANVIEW
$1,663
BALCONY
$2,111
SUITE
$4,335
Save (per person) 799
From (per person) 1,356
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 15 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Saint Vincent
Exclusive Deal
INSIDE
$1,931
OCEANVIEW
$2,182
BALCONY
$3,134
SUITE
$3,782
From (per person) 1,931
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 25 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Guadeloupe, Barbados
Exclusive Deal
INSIDE
$1,043
OCEANVIEW
$1,152
BALCONY
$1,686
SUITE
$2,082
From (per person) 1,043
View Trip
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 19 April 2026
Countries Visited: Puerto Rico, Saint Martin, Virgin Islands, Saint Kitts and Nevis (+2 more), Bahamas, USA
Exclusive DealSingle Savings
INSIDE
$1,211
OCEANVIEW
$1,404
BALCONY
$1,582
SUITE
$2,785
Save (per person) 689
From (per person) 1,211
View Trip
8 Day Southern Caribbean Cruise: Antigua, Grenada & Barbados with Azamara Cruises
Cruise
 (1)

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2025 to Dec 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
INSIDE
$1,887
OCEANVIEW
$2,372
BALCONY
$3,096
SUITE
$4,086
From (per person) 1,887
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: 23 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Curacao, Aruba
Exclusive Deal
INSIDE
$1,316
OCEANVIEW
$1,347
BALCONY
$1,517
SUITE
$2,964
Save (per person) 796
From (per person) 1,316
View Trip
15 Day West Indies to Iberia with Viking Cruises
Cruise
 (5)

15 Days (14 Nights) San Juan to Barcelona
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 29 March 2026
Countries Visited: Puerto Rico, Saint Martin, Portugal, Morocco (+1 more), Spain
Companion Fly Free
INSIDE
-
OCEANVIEW
-
BALCONY
$6,430
SUITE
$10,291
Save (per person) 1,665
From (per person) 6,430
View Trip
15 Day San Juan to Spanish Island Nights with Virgin Voyages
Cruise
 (5)

15 Days (14 Nights) San Juan to Barcelona
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 12 April 2025
Countries Visited: Puerto Rico, Spain, Morocco
80% Off Second SailorUp To USD $300 Bar Tab
INSIDE
$2,031
OCEANVIEW
$2,486
BALCONY
$2,941
SUITE
-
From (per person) 2,031
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
Departures: Nov 2025 to Apr 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Saint Lucia
Exclusive Deal
INSIDE
$1,063
OCEANVIEW
$1,169
BALCONY
$1,447
SUITE
$2,569
Save (per person) 846
From (per person) 1,063
View Trip
15 Day Caribbean Cruise: San Juan, St. Lucia & St. Kitts with Azamara Cruises
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2025 to Nov 2026
Countries Visited: 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
INSIDE
$3,666
OCEANVIEW
$4,498
BALCONY
$5,993
SUITE
$8,539
From (per person) 3,666
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Feb 2026
Countries Visited: Puerto Rico, Virgin Islands, Dominica, Saint Lucia (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$1,204
OCEANVIEW
$1,362
BALCONY
$1,793
SUITE
$2,313
From (per person) 1,204
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 18 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+3 more), Dominica, Barbados, Guadeloupe
Exclusive Deal
INSIDE
$1,988
OCEANVIEW
$2,242
BALCONY
$3,324
SUITE
$4,205
From (per person) 1,988
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 08 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Exclusive Deal
INSIDE
$2,086
OCEANVIEW
$2,364
BALCONY
$3,304
SUITE
$4,264
From (per person) 2,086
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 11 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+3 more), Saint Vincent, Barbados, Dominica
Exclusive Deal
INSIDE
$1,988
OCEANVIEW
$2,234
BALCONY
$3,572
SUITE
$4,294
From (per person) 1,988
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
Departures: Jan 2027 to Mar 2027
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+1 more), Saint Kitts and Nevis
Exclusive DealSingle Savings
INSIDE
$1,142
OCEANVIEW
$1,292
BALCONY
$1,720
SUITE
$2,946
Save (per person) 805
From (per person) 1,142
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: 07 December 2025
Countries Visited: Puerto Rico, Bonaire, Curacao, Aruba (+1 more), Virgin Islands
Exclusive Deal
INSIDE
$1,422
OCEANVIEW
$1,429
BALCONY
$1,819
SUITE
$3,273
Save (per person) 836
From (per person) 1,422
View Trip
19 Day Caribbean Holiday Cruise: San Juan, St. Barts & Curacao with Azamara Cruises
Cruise
 (1)

19 Days (18 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 18 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+8 more), Martinique, Galapagos, Trinidad and Tobago, Barbados, Curacao, Aruba, Saint Lucia, Saint Kitts and Nevis
INSIDE
$4,756
OCEANVIEW
$5,806
BALCONY
$7,766
SUITE
$12,597
From (per person) 4,756
View Trip
8 Day Caribbean Yachting Hideaways with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) San Juan to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departures: Feb 2025 to Feb 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy (+2 more), Montserrat, Antigua and Barbuda
Super Earlybird
INSIDE
-
OCEANVIEW
$6,440
BALCONY
-
SUITE
$7,796
Save (per person) 3,073
From (per person) 6,440
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 07 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+5 more), Saint Vincent, Barbados, Sint Maarten, Antigua and Barbuda, Dominica
Exclusive Deal
INSIDE
$2,383
OCEANVIEW
$2,644
BALCONY
-
SUITE
$3,967
From (per person) 2,383
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 25 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+4 more), Guadeloupe, Barbados, Saint Kitts and Nevis, Saint Vincent
Exclusive Deal
INSIDE
$2,205
OCEANVIEW
$2,506
BALCONY
$3,571
SUITE
$4,205
From (per person) 2,205
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+4 more), Dominica, Barbados, Guadeloupe, Grenada
Exclusive Deal
INSIDE
$2,541
OCEANVIEW
$2,843
BALCONY
$3,719
SUITE
$4,195
From (per person) 2,541
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 26 October 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Saint Vincent
Exclusive Deal
INSIDE
$2,185
OCEANVIEW
$2,447
BALCONY
$3,803
SUITE
$3,848
From (per person) 2,185
View Trip
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