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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 201 departures available from nine of the world's leading cruise lines.
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52 Cruises (201 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 1,234
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
Departure: 12 April 2026
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao (+1 more), Bonaire
Exclusive Deal
INSIDE
$2,058
OCEANVIEW
$2,174
BALCONY
$2,734
SUITE
$4,476
Save 680
From 1,655
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
$1,808
OCEANVIEW
$2,116
BALCONY
$2,539
SUITE
$4,178
Save 640
From 1,535
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
$1,882
OCEANVIEW
$2,175
BALCONY
$2,797
SUITE
$4,245
Save 634
From 1,581
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
$1,523
OCEANVIEW
$1,754
BALCONY
$3,742
SUITE
$3,933
Save 1,885
From 1,352
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
$1,707
OCEANVIEW
$1,981
BALCONY
$2,520
SUITE
$3,968
Save 588
From 1,448
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
11 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 16 February 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+3 more), Bonaire, Curacao, Aruba
Exclusive Deal
INSIDE
$2,250
OCEANVIEW
$2,455
BALCONY
-
SUITE
$5,795
Save 773
From 1,915
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
$1,525
OCEANVIEW
$1,559
BALCONY
$2,769
SUITE
$3,226
Save 886
From 1,306
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
$1,708
OCEANVIEW
$2,036
BALCONY
$2,500
SUITE
$3,840
Save 593
From 1,442
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
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Jun 2025 to Oct 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+1 more), Barbados
Exclusive Deal
INSIDE
$1,428
OCEANVIEW
$1,653
BALCONY
$2,856
SUITE
$3,095
Save 763
From 1,203
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
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: Jul 2024 to Oct 2025
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Bonaire (+1 more), Curacao
Exclusive Deal
INSIDE
$1,454
OCEANVIEW
$1,638
BALCONY
$2,792
SUITE
$2,969
Save 2,027
From 1,214
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
$1,713
OCEANVIEW
$1,918
BALCONY
$2,349
SUITE
$3,851
Save 601
From 1,454
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
$1,605
OCEANVIEW
$1,783
BALCONY
$2,452
SUITE
$3,750
Save 642
From 1,366
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
$1,888
OCEANVIEW
$2,196
BALCONY
$2,661
SUITE
$4,143
Save 661
From 1,595
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
$2,139
OCEANVIEW
$2,351
BALCONY
$2,685
SUITE
$4,249
Save 758
From 1,797
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
$1,759
OCEANVIEW
$2,196
BALCONY
$2,743
SUITE
$4,143
Save 749
From 1,485
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
$2,098
OCEANVIEW
$2,406
BALCONY
$2,959
SUITE
$4,407
Save 731
From 1,784
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
$2,200
OCEANVIEW
$2,344
BALCONY
$2,822
SUITE
$4,482
Save 783
From 1,873
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
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: Jan 2025 to Mar 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Martinique (+1 more), Barbados
Exclusive Deal
INSIDE
$1,774
OCEANVIEW
$1,904
BALCONY
$3,681
SUITE
$4,056
Save 647
From 1,535
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
$1,660
OCEANVIEW
$1,797
BALCONY
$2,351
SUITE
$3,567
Save 697
From 1,407
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
$1,892
OCEANVIEW
$2,179
BALCONY
$2,582
SUITE
$4,106
Save 663
From 1,592
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
$2,970
OCEANVIEW
$3,455
BALCONY
$4,124
SUITE
$4,761
From 2,970
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
12 Day Idyllic Isles of the Caribbean & Colombia with Virgin Voyages
Cruise
 (4)

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 21 January 2025
Countries Visited: Puerto Rico, Colombia, Curacao, Aruba (+3 more), Saint Lucia, Antigua and Barbuda, Saint Martin
INSIDE
$2,955
OCEANVIEW
$3,382
BALCONY
$3,614
SUITE
$8,069
From 2,955
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
$3,195
OCEANVIEW
$3,331
BALCONY
$3,802
SUITE
$4,409
From 3,195
View Trip
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