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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 230 departures available from ten of the world's leading cruise lines.
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71 Cruises (230 Cruise Departures)
11 Day West Indies Explorer with Viking Cruises
Cruise
 (5)

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
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
$2,824
OCEANVIEW
$3,103
BALCONY
$3,308
SUITE
$7,975
From 2,824
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: Jul 2024 to Apr 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia (+1 more), Barbados
Exclusive Deal
INSIDE
$1,449
OCEANVIEW
$1,589
BALCONY
$2,154
SUITE
$2,276
Save 2,052
From 1,258
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
$1,762
OCEANVIEW
$1,885
BALCONY
$2,641
SUITE
$3,814
Save 693
From 1,492
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
$2,098
OCEANVIEW
$2,515
BALCONY
$5,095
SUITE
$7,044
Save 820
From 1,848
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
$4,539
BALCONY
$5,574
SUITE
$7,885
From 3,474
View Trip
8 Day Southern Caribbean with Barbados with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Feb 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Martinique, Barbados
Exclusive Deal
INSIDE
$1,569
OCEANVIEW
$1,703
BALCONY
$2,193
SUITE
$2,658
From 1,569
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
$1,723
OCEANVIEW
$1,982
BALCONY
$2,384
SUITE
$3,741
Save 721
From 1,494
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
$1,701
OCEANVIEW
$1,940
BALCONY
$2,528
SUITE
$3,666
Save 787
From 1,479
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
INSIDE
$2,864
OCEANVIEW
$3,324
BALCONY
$4,385
SUITE
$4,700
From 2,864
View Trip
8 Day Southern Caribbean with Barbados with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Oct 2025 to Oct 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$1,554
OCEANVIEW
$1,688
BALCONY
$2,198
SUITE
$2,643
From 1,554
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
$2,183
OCEANVIEW
$2,318
BALCONY
$2,417
SUITE
$5,322
From 2,183
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
$3,122
OCEANVIEW
$3,322
BALCONY
$3,476
SUITE
$7,961
From 3,122
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
Ships: Resilient Lady, Valiant Lady
Departures: Dec 2024 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Lucia (+2 more), Antigua and Barbuda, Saint Martin
INSIDE
$1,976
OCEANVIEW
$2,076
BALCONY
$2,076
SUITE
$5,164
From 1,976
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
$1,394
OCEANVIEW
$1,600
BALCONY
$2,376
SUITE
$2,400
Save 884
From 1,261
View Trip
8 Day Southern Caribbean with Barbados with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Saint Vincent, Barbados
Exclusive Deal
INSIDE
$1,569
OCEANVIEW
$1,703
BALCONY
$2,193
SUITE
$2,654
From 1,569
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
$1,673
OCEANVIEW
$1,777
BALCONY
$3,325
SUITE
$3,777
Save 680
From 1,473
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
$4,175
BALCONY
$5,095
SUITE
$8,428
From 3,225
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
$2,776
OCEANVIEW
$2,944
BALCONY
$3,149
SUITE
$7,093
From 2,776
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
$1,471
OCEANVIEW
$1,635
BALCONY
$1,940
SUITE
$3,025
Save 763
From 1,263
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
$2,553
OCEANVIEW
$2,728
BALCONY
$2,986
SUITE
$6,649
From 2,553
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: Aug 2024 to Oct 2025
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Bonaire (+1 more), Curacao
Exclusive Deal
INSIDE
$1,305
OCEANVIEW
$1,409
BALCONY
$2,535
SUITE
$2,533
Save 1,051
From 1,119
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 Epic
Departure: 14 December 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+2 more), Saint Lucia, Saint Kitts and Nevis
INSIDE
$2,590
OCEANVIEW
-
BALCONY
$2,865
SUITE
$3,202
From 2,590
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
$2,573
OCEANVIEW
$2,782
BALCONY
$3,001
SUITE
$6,986
From 2,573
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
$1,645
OCEANVIEW
$1,795
BALCONY
$2,170
SUITE
$3,260
Save 682
From 1,423
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
$1,512
OCEANVIEW
$1,682
BALCONY
$2,023
SUITE
$3,215
Save 640
From 1,324
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
$2,165
OCEANVIEW
$2,432
BALCONY
$2,432
SUITE
$6,091
From 2,165
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
$1,567
OCEANVIEW
$1,621
BALCONY
$2,063
SUITE
$3,277
Save 664
From 1,371
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
$1,235
OCEANVIEW
$1,467
BALCONY
$2,545
SUITE
$2,707
Save 802
From 1,074
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
$1,861
OCEANVIEW
$3,354
BALCONY
$2,473
SUITE
$2,778
From 1,861
View Trip
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