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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 197 departures available from eight of the world's leading cruise lines.
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52 Cruises (197 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 1,172
From 5,440
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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
 (1)

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
$1,723
OCEANVIEW
$2,064
BALCONY
$2,350
SUITE
$3,919
Save 709
From 1,466
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8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

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
$1,526
OCEANVIEW
$1,698
BALCONY
$2,119
SUITE
$3,390
Save 737
From 1,318
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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 Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

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
$1,635
OCEANVIEW
$1,895
BALCONY
$2,365
SUITE
$3,790
Save 670
From 1,406
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8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

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
$1,742
OCEANVIEW
$2,049
BALCONY
$2,471
SUITE
$3,938
Save 714
From 1,492
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8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

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
$2,074
OCEANVIEW
$2,382
BALCONY
$2,749
SUITE
$4,229
Save 828
From 1,777
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: Brilliance of the Seas
Departure: 23 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Curacao, Aruba
Exclusive Deal
INSIDE
$2,073
OCEANVIEW
$2,299
BALCONY
$2,591
SUITE
$4,085
Save 845
From 1,770
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
$1,832
OCEANVIEW
$1,846
BALCONY
$4,622
SUITE
$4,012
Save 2,390
From 1,507
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
$1,368
OCEANVIEW
$1,546
BALCONY
$2,514
SUITE
$2,764
Save 2,548
From 1,160
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
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
$2,134
OCEANVIEW
$2,461
BALCONY
$3,573
SUITE
$4,145
Save 846
From 1,844
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: Brilliance of the Seas
Departure: 01 March 2026
Countries Visited: Puerto Rico, Curacao, Aruba, Virgin Islands
Exclusive Deal
INSIDE
$1,519
OCEANVIEW
$1,806
BALCONY
$2,200
SUITE
$3,722
Save 641
From 1,324
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
$3,968
SUITE
$4,439
From 3,134
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: Brilliance of the Seas
Departure: 12 April 2026
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao (+1 more), Bonaire
Exclusive Deal
INSIDE
$1,870
OCEANVIEW
$2,157
BALCONY
$2,470
SUITE
$4,203
Save 720
From 1,525
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: Brilliance of the Seas
Departures: Dec 2025 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Curacao, Aruba (+1 more), Bonaire
Exclusive Deal
INSIDE
$1,653
OCEANVIEW
$2,049
BALCONY
$2,491
SUITE
$3,938
Save 829
From 1,417
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
$1,420
OCEANVIEW
$1,500
BALCONY
$2,736
SUITE
$2,993
Save 1,024
From 1,259
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
$2,485
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: 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
$1,762
OCEANVIEW
$2,056
BALCONY
$2,608
SUITE
$4,019
Save 702
From 1,513
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
$1,880
OCEANVIEW
$3,486
BALCONY
$2,503
SUITE
$2,822
From 1,880
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
 (1)

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
$1,506
OCEANVIEW
$1,698
BALCONY
$2,228
SUITE
$3,510
Save 717
From 1,298
View Trip
10 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 07 March 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Sint Maarten (+2 more), Saint Lucia, Barbados
Exclusive Deal
INSIDE
$1,523
OCEANVIEW
$1,783
BALCONY
$3,052
SUITE
$3,206
Save 606
From 1,314
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
$2,714
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: Jan 2025 to Mar 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Martinique (+1 more), Barbados
Exclusive Deal
INSIDE
$1,627
OCEANVIEW
$1,771
BALCONY
$3,415
SUITE
$3,851
Save 709
From 1,453
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: Brilliance of the Seas
Departure: 04 January 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Grenada, Aruba (+1 more), Curacao
Exclusive Deal
INSIDE
$1,793
OCEANVIEW
$2,169
BALCONY
$2,461
SUITE
$3,901
Save 738
From 1,537
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
11 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 01 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao (+3 more), Bonaire, Grenada, Saint Vincent
Exclusive Deal
INSIDE
$2,266
OCEANVIEW
$2,566
BALCONY
$2,989
SUITE
$4,667
Save 909
From 1,942
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, Saint Lucia (+1 more), Barbados
Exclusive Deal
INSIDE
$1,479
OCEANVIEW
$1,684
BALCONY
$2,659
SUITE
$2,985
Save 677
From 1,277
View Trip
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