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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 363 departures available from eleven of the world's leading cruise lines.
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144 Cruises (363 Cruise Departures)
11 Day West Indies Explorer with Viking Cruises
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Operated By: 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
$6,561
SUITE
$9,991
Save (per person) 162
From (per person) 6,561
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: Feb 2027 to Apr 2027
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+2 more), Grenada, Saint Vincent
Exclusive Deal
INSIDE
$1,179
OCEANVIEW
$1,285
BALCONY
$1,734
SUITE
$3,134
Save (per person) 716
From (per person) 1,179
View Trip
15 Day Southern Caribbean Adventurer 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 (+4 more), Grenada, Barbados, Antigua and Barbuda, Saint Martin
Exclusive Deal
INSIDE
$2,383
OCEANVIEW
$2,645
BALCONY
$3,472
SUITE
$4,264
From (per person) 2,383
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
$1,029
OCEANVIEW
$1,215
BALCONY
$1,451
SUITE
$2,883
Save (per person) 706
From (per person) 1,029
View Trip
8 Day Southern Caribbean with Barbados and Antigua with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 March 2026
Countries Visited: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$993
OCEANVIEW
$1,141
BALCONY
$1,647
SUITE
$1,963
From (per person) 993
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 28 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Saint Kitts and Nevis, Saint Lucia, Grenada
Exclusive Deal
INSIDE
$3,670
OCEANVIEW
$4,138
BALCONY
$4,571
SUITE
$5,254
From (per person) 3,670
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 08 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Kitts and Nevis, Saint Lucia, Dominica, Grenada, Barbados
Exclusive Deal
INSIDE
$2,324
OCEANVIEW
$2,627
BALCONY
$3,591
SUITE
$4,561
From (per person) 2,324
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
$1,628
OCEANVIEW
$1,851
BALCONY
$2,346
SUITE
$3,597
Save (per person) 907
From (per person) 1,628
View Trip
8 Day Southern Caribbean with Barbados and Antigua Holiday with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 21 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Guadeloupe, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$1,557
OCEANVIEW
$1,771
BALCONY
$2,349
SUITE
$2,617
From (per person) 1,557
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
Departure: 30 March 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+1 more), Barbados
Exclusive Deal
INSIDE
$2,141
OCEANVIEW
-
BALCONY
-
SUITE
$5,468
Save (per person) 1,141
From (per person) 2,141
View Trip
15 Day Caribbean Cruise: San Juan, Antigua & Barbados with Azamara Cruises
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 21 November 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+9 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Saint Barthelemy
INSIDE
$3,676
OCEANVIEW
$4,508
BALCONY
$6,003
SUITE
$9,913
From (per person) 3,676
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
$1,441
OCEANVIEW
$1,659
BALCONY
$1,899
SUITE
$3,367
Save (per person) 851
From (per person) 1,441
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
$2,286
OCEANVIEW
-
BALCONY
$3,414
SUITE
$4,858
Save (per person) 1,203
From (per person) 2,286
View Trip
15 Day Southern Caribbean Adventurer 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, Saint Martin, Antigua and Barbuda (+2 more), Dominica, Barbados
Exclusive Deal
INSIDE
$1,839
OCEANVIEW
$2,125
BALCONY
$3,423
SUITE
$4,146
From (per person) 1,839
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
$1,059
OCEANVIEW
$1,138
BALCONY
$1,349
SUITE
$2,663
Save (per person) 671
From (per person) 1,059
View Trip
8 Day Southern Caribbean with Barbados and Antigua with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Grand Princess
Departures: Nov 2025 to Feb 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+2 more), Dominica, Barbados
Exclusive Deal
INSIDE
$964
OCEANVIEW
$1,092
BALCONY
$1,469
SUITE
$1,785
From (per person) 964
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
$1,291
OCEANVIEW
$1,339
BALCONY
$1,620
SUITE
$3,147
Save (per person) 781
From (per person) 1,291
View Trip
11 Day Puerto Rican Daze & Caribbean Nights with Virgin Voyages
Cruise
 (5)

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
Up To USD $300 Bar Tab
INSIDE
-
OCEANVIEW
-
BALCONY
$3,901
SUITE
$7,799
From (per person) 3,901
View Trip
8 Day San Juan, Barbados & Beyond with Virgin Voyages
Cruise
 (5)

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
$2,391
OCEANVIEW
-
BALCONY
-
SUITE
-
From (per person) 2,391
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts 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
$1,171
OCEANVIEW
$1,327
BALCONY
$1,785
SUITE
$2,221
From (per person) 1,171
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 23 November 2025
Countries Visited: Puerto Rico, Saint Martin, Saint Lucia, Barbados (+4 more), Grenada, Dominica, Virgin Islands, Antigua and Barbuda
Exclusive Deal
INSIDE
$2,581
OCEANVIEW
$2,916
BALCONY
$3,571
SUITE
$4,462
From (per person) 2,581
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
$1,968
OCEANVIEW
$2,332
BALCONY
$2,538
SUITE
$5,417
Save (per person) 1,068
From (per person) 1,968
View Trip
8 Day Southern Caribbean with Barbados and Antigua with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 29 March 2026
Countries Visited: Puerto Rico, Saint Martin, Dominica, Grenada (+2 more), Barbados, Virgin Islands
Exclusive Deal
INSIDE
$1,092
OCEANVIEW
$1,269
BALCONY
$1,646
SUITE
$2,122
From (per person) 1,092
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 DealExclusive Solo Offer
INSIDE
$1,564
OCEANVIEW
$1,787
BALCONY
$2,171
SUITE
$3,559
Save (per person) 893
From (per person) 1,564
View Trip
8 Day Southern Caribbean with Barbados and Antigua Holiday with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 28 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+2 more), Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
$2,777
BALCONY
$2,874
SUITE
$3,112
From (per person) 2,777
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
Ships: Crown Princess, Grand Princess
Departures: Oct 2025 to Mar 2027
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Exclusive Deal
INSIDE
$2,354
OCEANVIEW
$2,673
BALCONY
$3,670
SUITE
$4,621
From (per person) 2,354
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
$1,237
OCEANVIEW
$1,438
BALCONY
$1,888
SUITE
$2,929
Save (per person) 885
From (per person) 1,237
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
$1,440
OCEANVIEW
$1,560
BALCONY
$2,395
SUITE
$3,213
Save (per person) 823
From (per person) 1,440
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
$885
OCEANVIEW
$964
BALCONY
$1,942
SUITE
$2,534
Save (per person) 899
From (per person) 885
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, Aruba, Bonaire (+1 more), Curacao
Exclusive Deal
INSIDE
$839
OCEANVIEW
$973
BALCONY
$1,411
SUITE
$2,453
Save (per person) 902
From (per person) 839
View Trip
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