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Cruises Starting and Ending in San Juan

Are you looking for a cruise starting and ending in San Juan? December is the most popular month to join a roundtrip cruise from San Juan and we have 220 departures available from nine of the world's leading cruise lines.
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67 Cruises (220 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 1,077
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
$1,435
OCEANVIEW
$1,585
BALCONY
$2,118
SUITE
$3,249
Save 670
From 1,261
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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
$2,432
OCEANVIEW
$2,788
BALCONY
$2,981
SUITE
$7,131
From 2,432
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 Apr 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia (+1 more), Barbados
Exclusive Deal
INSIDE
$1,329
OCEANVIEW
$1,432
BALCONY
$2,038
SUITE
$2,676
Save 1,503
From 1,166
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
$2,219
OCEANVIEW
$2,536
BALCONY
$2,747
SUITE
$6,419
From 2,219
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
$2,166
OCEANVIEW
$2,501
BALCONY
-
SUITE
$6,802
Save 832
From 1,876
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
$2,977
OCEANVIEW
$3,409
BALCONY
$3,645
SUITE
$8,173
From 2,977
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
$1,634
OCEANVIEW
$1,921
BALCONY
$2,248
SUITE
$3,680
Save 686
From 1,419
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
$1,895
OCEANVIEW
$2,187
BALCONY
$2,752
SUITE
$3,872
Save 765
From 1,652
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
$2,724
OCEANVIEW
$3,118
BALCONY
$3,333
SUITE
$7,448
From 2,724
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
$2,950
OCEANVIEW
$3,376
BALCONY
$3,608
SUITE
$8,057
From 2,950
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
$1,985
OCEANVIEW
$2,122
BALCONY
$2,496
SUITE
$4,011
Save 817
From 1,729
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
Exclusive Solo Offer
INSIDE
$1,564
OCEANVIEW
$3,354
BALCONY
$2,176
SUITE
$2,481
From 1,564
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
Exclusive Solo Offer
INSIDE
$2,919
OCEANVIEW
$3,056
BALCONY
$3,531
SUITE
$4,142
From 2,919
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
$2,326
OCEANVIEW
$2,375
BALCONY
$2,518
SUITE
$5,454
From 2,326
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
$3,036
OCEANVIEW
$3,429
BALCONY
$3,780
SUITE
$8,402
From 3,036
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
$1,916
OCEANVIEW
$2,121
BALCONY
$2,365
SUITE
$3,730
Save 785
From 1,640
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, Saint Kitts and Nevis, Saint Lucia (+1 more), Barbados
Exclusive Deal
INSIDE
$1,358
OCEANVIEW
$1,568
BALCONY
$3,514
SUITE
$3,847
Save 1,999
From 1,332
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
$1,844
OCEANVIEW
$1,865
BALCONY
$2,546
SUITE
$3,938
Save 755
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: Jun 2024 to Oct 2024
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Saint Lucia, Barbados
Exclusive Deal
INSIDE
$1,478
OCEANVIEW
$1,766
BALCONY
$3,191
SUITE
$3,673
Save 3,073
From 1,253
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
$1,870
OCEANVIEW
$2,061
BALCONY
$2,421
SUITE
$3,957
Save 723
From 1,532
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
$1,570
OCEANVIEW
$1,707
BALCONY
$4,182
SUITE
$3,777
Save 696
From 1,393
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
$3,225
OCEANVIEW
$4,146
BALCONY
$5,066
SUITE
$8,399
From 3,225
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
$1,868
OCEANVIEW
$2,311
BALCONY
$4,372
SUITE
$4,291
Save 746
From 1,640
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
$1,335
OCEANVIEW
$1,485
BALCONY
$2,570
SUITE
$2,855
Save 795
From 1,335
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
$1,923
OCEANVIEW
$2,326
BALCONY
$3,459
SUITE
$3,772
Save 754
From 1,667
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
$1,485
OCEANVIEW
$1,771
BALCONY
$2,079
SUITE
$3,414
Save 615
From 1,297
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
$1,828
OCEANVIEW
$1,984
BALCONY
$2,250
SUITE
$3,586
Save 747
From 1,558
View Trip
15 Day Eastern Caribbean Voyage with Azamara Cruises
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Onward, Azamara Quest
Departures: Nov 2025 to Dec 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
$3,474
OCEANVIEW
$4,510
BALCONY
$5,545
SUITE
$7,856
From 3,474
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
$1,619
OCEANVIEW
$1,994
BALCONY
$2,491
SUITE
$3,733
Save 826
From 1,403
View Trip
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