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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 222 departures available from nine of the world's leading cruise lines.
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67 Cruises (222 Cruise Departures)
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: Oct 2024 to Mar 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+1 more), Barbados
Exclusive Deal
INSIDE
$1,233
OCEANVIEW
$1,343
BALCONY
$2,282
SUITE
$2,738
Save 804
From 1,115
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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 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
$1,702
OCEANVIEW
$2,009
BALCONY
$2,299
SUITE
$3,621
Save 673
From 1,452
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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
$1,509
OCEANVIEW
$1,865
BALCONY
$2,290
SUITE
$3,332
Save 604
From 1,306
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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
$2,035
OCEANVIEW
$2,191
BALCONY
$2,372
SUITE
$5,515
From 2,035
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
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
$1,659
OCEANVIEW
$1,986
BALCONY
$2,297
SUITE
$3,714
Save 669
From 1,436
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 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
$1,941
OCEANVIEW
$2,140
BALCONY
$2,415
SUITE
$3,764
Save 768
From 1,657
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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
$1,428
OCEANVIEW
$1,681
BALCONY
$2,844
SUITE
$2,889
Save 541
From 1,239
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8 Day Quaint Castries to Elegant Antigua with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 07 March 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Martinique (+2 more), Antigua and Barbuda, Virgin Islands
INSIDE
$2,231
OCEANVIEW
$2,487
BALCONY
$2,716
SUITE
$6,354
From 2,231
View Trip
8 Day Virgin Island Views & Saint Isle Blues with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Vincent (+1 more), Saint Kitts and Nevis
INSIDE
$2,127
OCEANVIEW
$2,382
BALCONY
$2,612
SUITE
$6,116
From 2,127
View Trip
11 Day Turquoise Shores, Hidden Isles with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 03 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive DealExclusive Solo Offer
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$10,059
SUITE
$11,544
Save 4,316
From 7,554
View Trip
8 Day Southern Caribbean - San Juan with Norwegian Cruise Line
Cruise

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
$2,293
OCEANVIEW
-
BALCONY
$2,721
SUITE
$2,905
From 2,293
View Trip
8 Day Aruban Sights & Antiguan Nights with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 03 January 2026
Countries Visited: Puerto Rico, Aruba, Curacao, Antigua and Barbuda (+1 more), Sint Maarten
INSIDE
$2,131
OCEANVIEW
$2,386
BALCONY
$2,616
SUITE
$6,120
From 2,131
View Trip
11 Day Sun-Soaked Seas & Saint Isles with Virgin Voyages
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 22 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+4 more), Martinique, Barbados, Saint Lucia, Sint Maarten
INSIDE
$3,194
OCEANVIEW
$3,552
BALCONY
$3,908
SUITE
$9,186
From 3,194
View Trip
11 Day Barefoot Reverie with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 20 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive Deal
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$9,910
SUITE
$11,682
Save 4,316
From 7,554
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12 Day Cartagena & Caribbean Faves with Virgin Voyages
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 02 December 2025
Countries Visited: Puerto Rico, Colombia, Curacao, Aruba (+3 more), Martinique, Antigua and Barbuda, Sint Maarten
INSIDE
$3,346
OCEANVIEW
$3,729
BALCONY
$4,087
SUITE
$9,604
From 3,346
View Trip
8 Day Sunny Miles of Tropical Isles with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Nov 2025 to Feb 2026
Countries Visited: Puerto Rico, Sint Maarten, Barbados, Saint Lucia (+2 more), Martinique, Saint Kitts and Nevis
INSIDE
$2,093
OCEANVIEW
$2,322
BALCONY
$2,552
SUITE
$5,950
From 2,093
View Trip
12 Day Cartagena, Aruba, Antigua & More with Virgin Voyages
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 February 2026
Countries Visited: Puerto Rico, Colombia, Curacao, Aruba (+1 more), Antigua and Barbuda
INSIDE
$3,497
OCEANVIEW
$3,930
BALCONY
$4,288
SUITE
$10,111
From 3,497
View Trip
8 Day Southern Caribbean Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 30 November 2024
Countries Visited: Puerto Rico, Sint Maarten, Saint Lucia, Barbados (+2 more), Dominica, Antigua and Barbuda
Exclusive Deal
INSIDE
$1,412
OCEANVIEW
$1,648
BALCONY
$2,123
SUITE
$3,538
Save 2,762
From 1,412
View Trip
8 Day St. Kitts, Barbados, Martinique & More with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 17 January 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Barbados, Martinique (+2 more), Antigua and Barbuda, Sint Maarten
INSIDE
$2,285
OCEANVIEW
$2,540
BALCONY
$2,796
SUITE
$6,514
From 2,285
View Trip
8 Day Joy Of The Islands with Regent Seven Seas
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 13 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+3 more), Saint Lucia, Antigua and Barbuda, Saint Barthelemy
Exclusive Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
$5,997
BALCONY
$7,254
SUITE
$8,581
Save 3,553
From 5,997
View Trip
8 Day Valiant New Year's Ahoy! with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 27 December 2025
Countries Visited: Puerto Rico, Sint Maarten, Saint Kitts and Nevis, Saint Lucia (+2 more), Barbados, Virgin Islands
INSIDE
$3,111
OCEANVIEW
$3,468
BALCONY
$3,801
SUITE
$9,050
From 3,111
View Trip
8 Day St. Lucia, St. Maarten, Barbados & More with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 13 December 2025
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Dominica (+2 more), Barbados, Sint Maarten
INSIDE
$2,091
OCEANVIEW
$2,320
BALCONY
$2,550
SUITE
$5,948
From 2,091
View Trip
13 Day Treasures Of Aruba, Bonaire & Curacao with Seabourn
Cruise

13 Days (12 Nights) San Juan to San Juan
Cruise Line: Seabourn
Ship: Ovation
Departure: 02 December 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+6 more), Martinique, Dominica, Montserrat, Saint Kitts and Nevis, Antigua and Barbuda, Virgin Islands
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$7,585
SUITE
$15,243
From 7,585
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 17 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Martinique (+1 more), Barbados
Exclusive Deal
INSIDE
$1,675
OCEANVIEW
$1,989
BALCONY
$2,347
SUITE
$3,553
Save 654
From 1,472
View Trip
8 Day Sunsets in the Lesser Antilles with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jan 2025 to Mar 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Martinique, Curacao (+1 more), Aruba
INSIDE
$1,945
OCEANVIEW
$2,174
BALCONY
$2,393
SUITE
$5,265
From 1,945
View Trip
8 Day Southern Caribbean Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departures: Oct 2024 to Dec 2024
Countries Visited: Puerto Rico, Sint Maarten, Antigua and Barbuda, Saint Lucia (+2 more), Barbados, Dominica
Exclusive DealExclusive Offer
INSIDE
$1,249
OCEANVIEW
$1,399
BALCONY
$1,802
SUITE
$3,843
Save 4,891
From 1,249
View Trip
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