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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 263 departures available from ten of the world's leading cruise lines.
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150 Cruises (263 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: Dec 2025 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
Viking $699 Air Deal
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
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: 12 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Saint Lucia, Grenada
Exclusive Savings
Inside
$753
Oceanview
$748
Balcony
$1,045
Suite
$3,513
From
US$748
Save 546
Per Person
View Trip
8 Day Aruban Sights & Antiguan Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2026 to Feb 2027
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Sint Maarten
Black Friday Deal
Inside
$903
Oceanview
$1,043
Balcony
$1,323
Suite
$3,010
From
US$903
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 February 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Kitts and Nevis, Saint Lucia, Dominica, Grenada, Barbados
Princess Standard
Inside
$1,516
Oceanview
-
Balcony
-
Suite
-
From
US$1,516
Per Person
View Trip
7 Day Caribbean East: Virgin & Saint Isles 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
Black Friday Deal
Inside
$834
Oceanview
$1,014
Balcony
$1,194
Suite
$3,540
From
US$834
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
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$750
Oceanview
$859
Balcony
$1,200
Suite
$1,500
From
US$750
Per Person
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
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Grenada, Barbados
Princess Standard
Inside
$597
Oceanview
$677
Balcony
$1,127
Suite
$1,277
From
US$597
Per Person
View Trip
8 Day Saint Isles & The Greater Antilles with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 20 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Lucia, Barbados, Dominica, Saint Martin
Black Friday Deal
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$4,130
From
US$1,043
Per Person
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (6)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Emerald Princess
Departures: Dec 2026 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
$1,519
Oceanview
$1,749
Balcony
$2,519
Suite
$3,069
From
US$1,519
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
$603
Oceanview
$658
Balcony
$1,171
Suite
$1,536
From
US$603
Save 461
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Antigua with Princess
Cruise
 (6)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Grand Princess
Departures: Dec 2025 to Feb 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica, Barbados
Princess Standard
Inside
$549
Oceanview
$637
Balcony
$829
Suite
$1,077
From
US$549
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: 15 March 2026
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$708
Oceanview
$738
Balcony
$979
Suite
$2,382
From
US$708
Save 419
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 25 April 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
$680
Oceanview
$683
Balcony
$1,017
Suite
$1,860
From
US$680
Save 428
Per Person
View Trip
11 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 01 February 2026
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao, Bonaire, Barbados, Saint Vincent
Exclusive Savings
Inside
$1,230
Oceanview
$1,399
Balcony
$2,200
Suite
$4,510
From
US$1,230
Save 659
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Tortola Holiday with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$1,100
Oceanview
$1,269
Balcony
$1,750
Suite
$2,050
From
US$1,100
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 04 January 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Grenada, Barbados
Princess Standard
Inside
-
Oceanview
$827
Balcony
$1,549
Suite
$2,708
From
US$827
Per Person
View Trip
22 Day San Juan to San Juan with Silversea
Cruise

22 Days (21 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+8 more), Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda, Dominica, Curacao, Bonaire
All-Inclusive Fare
Inside
-
Oceanview
$8,100
Balcony
$9,300
Suite
$17,000
From
US$8,100
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 16 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Barbados, Saint Lucia
Princess Standard
Inside
$850
Oceanview
$969
Balcony
$1,350
Suite
$1,650
From
US$850
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: Feb 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$1,027
Oceanview
$1,112
Balcony
$1,327
Suite
$1,677
From
US$1,027
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: 17 January 2027
Visit: Puerto Rico, Barbados, Grenada, Saint Lucia, Antigua and Barbuda, Saint Martin, Virgin Islands
Princess Standard
Inside
$1,946
Oceanview
$2,216
Balcony
$2,796
Suite
$3,392
From
US$1,946
Per Person
View Trip
8 Day Southern Caribbean with Antigua and St. Kitts with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 08 February 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, Saint Lucia
Princess Standard
Inside
$717
Oceanview
$687
Balcony
$1,397
Suite
$1,647
From
US$687
Per Person
View Trip
8 Day St. Lucia, Barbados & More with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 07 February 2026
Visit: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Saint Lucia, Barbados, Virgin Islands
Black Friday Deal
Inside
$693
Oceanview
$1,043
Balcony
$1,253
Suite
$3,395
From
US$693
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, Antigua and Barbuda, Martinique
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,400
Balcony
$4,000
Suite
$10,700
From
US$3,400
Save 3,000
Per Person
View Trip
8 Day Antigua & the St. Isles with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 January 2026
Visit: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia, Virgin Islands
Black Friday Deal
Inside
$693
Oceanview
$973
Balcony
$1,253
Suite
$2,863
From
US$693
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
Black Friday Deal
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
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 22 March 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Barbados
Exclusive Savings
Inside
$649
Oceanview
$749
Balcony
$999
Suite
$1,877
From
US$649
Save 501
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: Feb 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
$1,709
Oceanview
$1,969
Balcony
$2,509
Suite
$3,209
From
US$1,709
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
$759
Oceanview
$809
Balcony
$999
Suite
$1,941
From
US$759
Save 525
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
$3,911
Oceanview
$4,522
Balcony
$5,512
Suite
$9,246
From
US$3,911
Save 88
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: 16 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Barbados, Saint Lucia, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$1,659
Oceanview
$1,909
Balcony
$2,659
Suite
$3,259
From
US$1,659
Per Person
View Trip
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