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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 203 departures available from nine of the world's leading cruise lines.
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52 Cruises (203 Cruise Departures)
11 Day West Indies Explorer with Viking Cruises
Cruise
 (4)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departures: Oct 2024 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Discover More Sale
INSIDE
-
OCEANVIEW
-
BALCONY
$5,440
SUITE
$9,400
Save 1,120
From 5,440
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 Deal
INSIDE
$1,530
OCEANVIEW
$1,709
BALCONY
$2,353
SUITE
$3,579
Save 694
From 1,315
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: Jun 2024 to Oct 2024
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Saint Lucia, Barbados
Exclusive Deal
INSIDE
$1,809
OCEANVIEW
$1,685
BALCONY
$3,373
SUITE
$4,122
Save 1,313
From 1,483
View Trip
9 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 24 May 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+2 more), Barbados, Saint Lucia
Exclusive Deal
INSIDE
$2,043
OCEANVIEW
$2,486
BALCONY
$3,664
SUITE
$4,200
Save 775
From 1,745
View Trip
8 Day Southern Caribbean - San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Ship: Norwegian Viva
Departure: 19 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+2 more), Saint Lucia, Sint Maarten
Free At Sea Offer
INSIDE
$2,940
OCEANVIEW
$3,455
BALCONY
$4,124
SUITE
$4,761
From 2,940
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: 22 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Barbados
Exclusive Deal
INSIDE
$1,808
OCEANVIEW
$2,101
BALCONY
$2,698
SUITE
$4,075
Save 686
From 1,529
View Trip
12 Day Colombia & Caribbean Islands with Virgin Voyages
Cruise
 (4)

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 01 April 2025
Countries Visited: Puerto Rico, Colombia, Aruba, Curacao (+3 more), Dominica, Antigua and Barbuda, Saint Martin
INSIDE
$2,981
OCEANVIEW
$3,415
BALCONY
$3,651
SUITE
$8,185
From 2,981
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
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Grenada, Aruba (+1 more), Curacao
Exclusive Deal
INSIDE
$1,818
OCEANVIEW
$2,105
BALCONY
$2,483
SUITE
$3,935
Save 714
From 1,541
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
Countries Visited: Puerto Rico, Curacao, Aruba, Virgin Islands
Exclusive Deal
INSIDE
$1,639
OCEANVIEW
$1,844
BALCONY
$2,250
SUITE
$3,681
Save 653
From 1,402
View Trip
8 Day Resilient New Year's Ahoy with Virgin Voyages
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 28 December 2024
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Lucia (+2 more), Antigua and Barbuda, Saint Martin
INSIDE
$3,041
OCEANVIEW
$3,436
BALCONY
$3,787
SUITE
$8,416
From 3,041
View Trip
8 Day Saint (Isles) & Seas of the Caribbean with Virgin Voyages
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: Dec 2024 to Mar 2025
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Lucia (+2 more), Antigua and Barbuda, Saint Martin
INSIDE
$2,039
OCEANVIEW
$2,196
BALCONY
$2,376
SUITE
$5,524
From 2,039
View Trip
11 Day San Juan, St. Vincent, Barbados & More with Virgin Voyages
Cruise
 (4)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 11 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+4 more), Martinique, Barbados, Saint Lucia, Saint Vincent
INSIDE
$2,852
OCEANVIEW
$3,082
BALCONY
$3,389
SUITE
$7,376
From 2,852
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: 15 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao (+1 more), Bonaire
Exclusive Deal
INSIDE
$1,814
OCEANVIEW
$2,122
BALCONY
$2,562
SUITE
$3,972
Save 712
From 1,544
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: 28 December 2025
Countries Visited: Puerto Rico, Antigua and Barbuda, Saint Lucia, Saint Kitts and Nevis (+1 more), Virgin Islands
Exclusive Deal
INSIDE
$2,023
OCEANVIEW
$2,331
BALCONY
$2,860
SUITE
$4,236
Save 783
From 1,732
View Trip
8 Day Southern Caribbean - San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Ship: Norwegian Viva
Departures: Dec 2024 to Apr 2025
Countries Visited: Puerto Rico, Dominican Republic, Aruba, Curacao (+3 more), Bonaire, Saint Lucia, Saint Kitts and Nevis
Free At Sea OfferExclusive Solo Offer
INSIDE
$3,134
OCEANVIEW
$3,331
BALCONY
$3,802
SUITE
$4,409
From 3,134
View Trip
8 Day Resilient Caribbean Holidays with Virgin Voyages
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 21 December 2024
Countries Visited: Puerto Rico, Saint Martin, Barbados, Saint Lucia (+2 more), Martinique, Saint Kitts and Nevis
INSIDE
$2,436
OCEANVIEW
$2,792
BALCONY
$2,986
SUITE
$7,142
From 2,436
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: May 2024 to Oct 2024
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+1 more), Barbados
Exclusive Deal
INSIDE
$1,449
OCEANVIEW
$1,679
BALCONY
$3,643
SUITE
$4,189
Save 1,927
From 1,300
View Trip
9 Day Pre-Holiday Caribbean Refresh with Virgin Voyages
Cruise
 (4)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 06 December 2024
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Barbados (+3 more), Martinique, Saint Lucia, Saint Kitts and Nevis
INSIDE
$2,223
OCEANVIEW
$2,541
BALCONY
$2,753
SUITE
$6,430
From 2,223
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: 09 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao
Exclusive Deal
INSIDE
$1,634
OCEANVIEW
$1,962
BALCONY
$2,401
SUITE
$3,668
Save 645
From 1,390
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: 18 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Grenada (+2 more), Saint Vincent, Dominica
Exclusive Deal
INSIDE
$1,734
OCEANVIEW
$2,042
BALCONY
$2,440
SUITE
$4,008
Save 692
From 1,483
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
Ships: Rhapsody of the Seas, Rhapsody of the Seas
Departures: Jun 2024 to Oct 2025
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Bonaire (+1 more), Curacao
Exclusive Deal
INSIDE
$1,379
OCEANVIEW
$1,564
BALCONY
$2,693
SUITE
$2,799
Save 2,590
From 1,163
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 Deal
INSIDE
$1,684
OCEANVIEW
$2,122
BALCONY
$2,644
SUITE
$3,972
Save 800
From 1,434
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
$1,633
OCEANVIEW
$1,906
BALCONY
$2,421
SUITE
$3,797
Save 640
From 1,396
View Trip
14 Day Eastern Caribbean Voyage with Azamara Cruises
Cruise
 (1)

14 Days (13 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 December 2025
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, Sint Maarten
INSIDE
$3,456
OCEANVIEW
$4,146
BALCONY
$5,066
SUITE
$8,399
From 3,456
View Trip
8 Day San Juan, Barbados & Beyond with Virgin Voyages
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 01 March 2025
Countries Visited: Puerto Rico, Saint Martin, Saint Lucia, Barbados (+2 more), Martinique, Saint Kitts and Nevis
INSIDE
$2,330
OCEANVIEW
$2,379
BALCONY
$2,522
SUITE
$5,462
From 2,330
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: Oct 2024 to Mar 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+1 more), Barbados
Exclusive Deal
INSIDE
$1,451
OCEANVIEW
$1,485
BALCONY
$2,670
SUITE
$3,056
Save 937
From 1,255
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: 12 April 2026
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao (+1 more), Bonaire
Exclusive Deal
INSIDE
$1,984
OCEANVIEW
$2,099
BALCONY
$2,635
SUITE
$4,305
Save 732
From 1,603
View Trip
9 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 13 April 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+2 more), Barbados, Dominica
Exclusive Deal
INSIDE
$1,950
OCEANVIEW
$2,257
BALCONY
$4,281
SUITE
$4,626
Save 751
From 1,692
View Trip
8 Day Caribbean Cruise with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Ships: Norwegian Epic, Norwegian Viva
Departures: Dec 2024 to Apr 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados (+2 more), Saint Lucia, Sint Maarten
Free At Sea OfferExclusive Solo Offer
INSIDE
$1,850
OCEANVIEW
$3,547
BALCONY
$2,458
SUITE
$2,760
From 1,850
View Trip
11 Day Puerto Rican Daze & Caribbean Nights with Virgin Voyages
Cruise
 (4)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 22 March 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+4 more), Martinique, Saint Lucia, Barbados, Saint Vincent
INSIDE
$2,729
OCEANVIEW
$3,123
BALCONY
$3,339
SUITE
$7,461
From 2,729
View Trip
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