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Round-trip Cruises from 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 304 departures available from ten of the world's leading cruise lines.
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147 Cruises (304 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
Ships: Viking Sea, Viking Sky
Departures: Nov 2026 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Viking $799 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
Save 100
Per Person
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
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$879
Oceanview
$898
Balcony
$1,057
Suite
$1,736
From
US$879
Save 491
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Tortola with Princess
Cruise
 (6)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$774
Oceanview
$874
Balcony
$1,099
Suite
$1,499
From
US$774
Per Person
View Trip
9 Day Barbados, Dominica & St. Isle Spring with Virgin Voyages
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 March 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Dominica, Saint Martin
Inside
$1,192
Oceanview
$1,432
Balcony
$1,672
Suite
$4,720
From
US$1,192
Per Person
View Trip
12 Day San Juan to San Juan with Silversea
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 25 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Dominica (+4 more), Saint Vincent, Grenada, Curacao, Bonaire
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,800
Balcony
$5,520
Suite
$11,240
From
US$4,800
Save 1,200
Per Person
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 Constellation
Departure: 20 March 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,009
Oceanview
$1,059
Balcony
$1,234
Suite
$2,234
From
US$1,009
Save 645
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
$775
Oceanview
$884
Balcony
$1,250
Suite
$1,600
From
US$775
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 24 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$1,052
Oceanview
$1,122
Balcony
$1,902
Suite
$2,112
From
US$1,052
Save 546
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (6)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,759
Oceanview
$1,918
Balcony
$2,390
Suite
$3,104
From
US$1,759
Per Person
View Trip
8 Day Southern Caribbean From San Juan To San Juan with Norwegian Cruise Line
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Nov 2026 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Saint Martin
Exclusive Savings
Inside
$1,219
Oceanview
$1,319
Balcony
$1,589
Suite
$2,225
From
US$1,219
Save 54
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (6)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 17 January 2027
Visit: Puerto Rico, Barbados, Grenada, Saint Lucia, Antigua and Barbuda, Saint Martin
Princess Standard
Inside
$774
Oceanview
$874
Balcony
$999
Suite
$1,699
From
US$774
Per Person
View Trip
19 Day Caribbean Holiday Cruise: San Juan, St. Barts & Curacao with Azamara Cruises
Cruise
 (3)

19 Days (18 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 18 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+8 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis
Azamara Always Included
Exclusive Savings
Inside
$4,862
Oceanview
$5,133
Balcony
$6,346
Suite
$10,022
From
US$4,862
Save 117
Per Person
View Trip
8 Day Valiant New Year's Ahoy! with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 26 December 2026
Visit: Puerto Rico, Saint Martin, Martinique, Barbados, Saint Lucia, Antigua and Barbuda
Inside
$1,743
Oceanview
$1,883
Balcony
$2,093
Suite
$4,620
From
US$1,743
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 18 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda
Bonus Onboard Credit
Exclusive Savings
Inside
$794
Oceanview
$854
Balcony
$1,374
Suite
$1,509
From
US$794
Save 445
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 Dawn
Departure: 21 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,680
Balcony
$4,240
Suite
$8,560
From
US$3,680
Save 920
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 20 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,809
Oceanview
$2,079
Balcony
$2,769
Suite
$3,207
From
US$1,809
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
Departures: Dec 2027 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$732
Oceanview
$792
Balcony
$1,332
Suite
$1,462
From
US$732
Save 435
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, St. Lucia & St. Kitts with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2026 to Dec 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
Exclusive Savings
Inside
$3,503
Oceanview
$4,112
Balcony
$5,267
Suite
$8,041
From
US$3,503
Save 87
Per Person
View Trip
14 Day Caribbean Cruise: San Juan, Antigua & St. Lucia with Azamara Cruises
Cruise
 (3)

14 Days (13 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 05 December 2026
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
Exclusive Savings
Inside
$3,074
Oceanview
$3,345
Balcony
$4,364
Suite
$6,886
From
US$3,074
Save 65
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (6)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 10 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados, Grenada
Princess Standard
Inside
$1,668
Oceanview
$1,818
Balcony
$2,268
Suite
$3,313
From
US$1,668
Per Person
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: 15 March 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$1,114
Oceanview
$1,496
Balcony
$3,837
Suite
-
From
US$1,114
Per Person
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 March 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+4 more), Dominica, Barbados, Saint Kitts and Nevis, Grenada
Princess Standard
Inside
$1,434
Oceanview
$1,945
Balcony
$2,376
Suite
$2,726
From
US$1,434
Per Person
View Trip
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Nov 2027 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Montserrat, Antigua and Barbuda, Guadeloupe
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$11,667
Balcony
-
Suite
$15,208
From
US$11,667
Save 12,828
Per Person
View Trip
8 Day Saint (Isles) & Seas of the Caribbean with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 06 March 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$4,130
From
US$1,043
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
Departures: Feb 2028 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$779
Oceanview
$840
Balcony
$1,499
Suite
$1,629
From
US$779
Save 495
Per Person
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 Constellation
Departure: 06 February 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Lucia, Grenada
Exclusive Savings
Inside
$880
Oceanview
$930
Balcony
$1,105
Suite
$3,041
From
US$880
Save 573
Per Person
View Trip
9 Day A Journey From San Juan To San Juan with Explora Journeys
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 03 March 2026
Visit: Puerto Rico, Grenada, Saint Vincent, Barbados, Martinique, Saint Barthelemy, Saint Kitts and Nevis
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,635
Suite
$5,220
From
US$4,635
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (4)

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
Exclusive Savings
Inside
$3,717
Oceanview
$4,697
Balcony
$5,715
Suite
$8,693
From
US$3,717
Save 82
Per Person
View Trip
8 Day Valiant's Haunted Halloween Soiree with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
-
Oceanview
$1,183
Balcony
$1,393
Suite
$4,200
From
US$1,183
Per Person
View Trip
8 Day West Indies Island Hopping with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 27 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,303
Balcony
-
Suite
$7,073
From
US$5,303
Save 7,687
Per Person
View Trip
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