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Cruises from San Juan

Choose from 235 unique cruises starting in San Juan, and traveling to Barcelona, Bridgetown, Colon, Fort Lauderdale, Lisbon and more. December is the most popular month to join a cruise from San Juan and you can select from 396 departures available from twelve leading cruise lines.
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235 Cruises (396 Cruise Departures)
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 28 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$1,253
Oceanview
$1,323
Balcony
$1,393
Suite
$2,863
From
US$1,253
Per Person
View Trip
16 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (5)

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin
Azamara Always Included
Inside
$4,089
Oceanview
$5,099
Balcony
$6,289
Suite
$9,529
From
US$4,089
Per Person
View Trip
8 Day Quintessential Caribbean with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Antigua and Barbuda, Saint Barthelemy
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$4,788
Balcony
-
Suite
$6,187
From
US$4,788
Save 1,603
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 17 January 2027
Visit: Puerto Rico, Bonaire, Curacao, Virgin Islands
Inside
$1,359
Oceanview
$1,429
Balcony
$1,559
Suite
$2,009
From
US$1,359
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Limited Time Offer
Inside
$834
Oceanview
$1,014
Balcony
$1,194
Suite
$3,414
From
US$834
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (9)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 17 January 2027
Visit: Puerto Rico, Saint Martin, Martinique, Grenada, Saint Lucia, Barbados
Princess Standard
Inside
$839
Oceanview
$899
Balcony
$1,454
Suite
$2,029
From
US$839
Per Person
View Trip
9 Day Caribbean Essence with Oceania Cruises
Cruise

9 Days (8 Nights) San Juan to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 19 February 2027
Visit: Puerto Rico, Saint Barthelemy, Saint Martin, Saint Kitts and Nevis, Antigua and Barbuda, Virgin Islands, USA
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,299
Suite
$5,349
From
US$3,299
Save 3,299
Per Person
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 07 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,052
From
US$5,052
Save 1,403
Per Person
View Trip
15 Day An Extended Journey from Ocean Calm to Vibrant Culture with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 07 March 2027
Visit: Puerto Rico, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis (+6 more), Turks and Caicos Islands, USA, Antigua and Barbuda, Dominica, Saint Vincent, Barbados
Inside
-
Oceanview
-
Balcony
-
Suite
$7,575
From
US$7,575
Per Person
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$1,588
Oceanview
$1,878
Balcony
$2,208
Suite
$3,208
From
US$1,588
Per Person
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: Vision of the Seas
Departures: Nov 2026 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$684
Oceanview
$727
Balcony
$1,196
Suite
$1,190
From
US$684
Save 450
Per Person
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: Vision of the Seas
Departures: Jan 2028 to Mar 2028
Visit: Puerto Rico, Barbados, Grenada, Saint Lucia, Antigua and Barbuda, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$784
Oceanview
$834
Balcony
$1,443
Suite
$1,594
From
US$784
Save 447
Per Person
View Trip
8 Day A Journey Through Historical Gems & Idyllic Coastlines with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Martin, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
9 Day Southern Caribbean Cruise: Martinique, Grenada & U.S. Virgin Islands with Azamara Cruises
Cruise
 (5)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,229
Oceanview
$2,789
Balcony
$3,389
Suite
$5,149
From
US$2,229
Per Person
View Trip
17 Day An Extended Journey of Dazzling Skylines & Wildlife Exploration with Explora Journeys
Cruise

17 Days (16 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 04 January 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Montserrat, Virgin Islands, USA, Dominican Republic
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$8,120
From
US$8,120
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 20 December 2026
Visit: Puerto Rico, Virgin Islands, Montserrat, Saint Lucia, Martinique
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,200
Balcony
$4,900
Suite
$8,600
From
US$4,200
Save 1,500
Per Person
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: Vision of the Seas
Departure: 28 February 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique, Saint Vincent, Grenada
Bonus Onboard Credit
Exclusive Savings
Inside
$699
Oceanview
$955
Balcony
$2,128
Suite
$2,058
From
US$699
Save 405
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Tortola with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$719
Oceanview
$919
Balcony
$1,094
Suite
$1,469
From
US$719
Per Person
View Trip
9 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 12 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Dominica, Saint Martin
Limited Time Offer
Inside
$952
Oceanview
$1,112
Balcony
$1,512
Suite
$4,320
From
US$952
Per Person
View Trip
8 Day A Journey Through Tropical Utopia & Rhythmic Streets with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 12 March 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 31 January 2027
Visit: Puerto Rico, Curacao, Aruba, Virgin Islands
Inside
$1,439
Oceanview
$1,509
Balcony
$1,609
Suite
$2,089
From
US$1,439
Per Person
View Trip
8 Day A Journey Through Caribbean Jewels with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 29 April 2028
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Kitts and Nevis, Saint Martin, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
Per Person
View Trip
9 Day Southern Caribbean & Aruban Holidays with Virgin Voyages
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 18 December 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Aruba, Curacao
Limited Time Offer
Inside
$1,112
Oceanview
$1,272
Balcony
$1,592
Suite
$4,960
From
US$1,112
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 28 February 2027
Visit: Puerto Rico, Virgin Islands, Dominica, Barbados, Saint Martin
Inside
$1,519
Oceanview
$1,579
Balcony
$1,719
Suite
$2,009
From
US$1,519
Per Person
View Trip
8 Day Southern Caribbean From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Dec 2026 to Feb 2027
Visit: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Barbados, Saint Lucia, Virgin Islands
Inside
$1,549
Oceanview
$1,649
Balcony
$2,049
Suite
$2,819
From
US$1,549
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: Jan 2028 to Mar 2028
Visit: Puerto Rico, Saint Martin, Barbados, Martinique, Saint Kitts and Nevis, Virgin Islands
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Martin, Barbados
Inside
$1,259
Oceanview
$1,459
Balcony
$1,709
Suite
$2,609
From
US$1,259
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 21 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin
Azamara Always Included
Inside
$3,799
Oceanview
$4,809
Balcony
$5,859
Suite
$8,929
From
US$3,799
Per Person
View Trip
12 Day Mid Atlantic Crossing with Viking Cruises
New ReleaseCruise
 (5)

12 Days (11 Nights) San Juan to Lisbon
Cruise Line: Viking Cruises
Ship: Viking Sky
Departure: 27 February 2028
Visit: Puerto Rico, Spain, Portugal
Viking $999 Air Deal
Inside
-
Oceanview
-
Balcony
$3,099
Suite
$5,499
From
US$3,099
Per Person
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: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Dominica, Antigua and Barbuda, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$756
Oceanview
$826
Balcony
$1,455
Suite
$1,606
From
US$756
Save 422
Per Person
View Trip
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