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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 310 departures available from ten of the world's leading cruise lines.
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156 Cruises (310 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
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
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
$3,209
From
US$1,809
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
With Love From the World
Inside
$1,870
Oceanview
-
Balcony
$1,372
Suite
$2,863
From
US$1,372
Per Person
View Trip
8 Day Antigua, Martinique, & Barbados & More with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 21 February 2026
Visit: Puerto Rico, Sint Maarten, Barbados, Martinique, Antigua and Barbuda, Virgin Islands
With Love From the World
Inside
$903
Oceanview
$973
Balcony
$1,253
Suite
$3,325
From
US$903
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
Exclusive Savings
Inside
$670
Oceanview
$730
Balcony
$1,250
Suite
$1,410
From
US$670
Save 392
Per Person
View Trip
8 Day Virgin Island Views & Saint Isle Blues with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 January 2026
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Saint Kitts and Nevis
With Love From the World
Inside
-
Oceanview
-
Balcony
$1,370
Suite
$3,010
From
US$1,370
Per Person
View Trip
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 03 January 2026
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Sint Maarten, Montserrat, Antigua and Barbuda, Guadeloupe
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$61,421
From
US$61,421
Save 1,859
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 Feb 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Saint Martin
Exclusive Savings
Inside
$1,239
Oceanview
-
Balcony
$1,729
Suite
$2,948
From
US$1,239
Save 91
Per Person
View Trip
8 Day Sunny Miles of Tropical Isles with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Feb 2026 to Jan 2027
Visit: Puerto Rico, Sint Maarten, Barbados, Saint Lucia, Martinique, Saint Kitts and Nevis
With Love From the World
Inside
$903
Oceanview
$973
Balcony
$1,237
Suite
$3,465
From
US$903
Per Person
View Trip
8 Day Valiant Caribbean Holidays with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Martinique, Aruba, Curacao
With Love From the World
Inside
$1,323
Oceanview
$1,533
Balcony
$1,736
Suite
$4,620
From
US$1,323
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
$1,052
Oceanview
$1,137
Balcony
$1,377
Suite
$1,777
From
US$1,052
Per Person
View Trip
15 Day Southern Caribbean Adventurer Holiday with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$2,269
Oceanview
$2,619
Balcony
$3,611
Suite
$4,199
From
US$2,269
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
$1,759
Oceanview
$2,019
Balcony
$2,559
Suite
$3,209
From
US$1,759
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: 09 January 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
$1,719
Oceanview
$1,969
Balcony
$2,719
Suite
$3,219
From
US$1,719
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
$577
Oceanview
$573
Balcony
$1,077
Suite
$1,227
From
US$573
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
Exclusive Savings
Inside
$1,052
Oceanview
$1,122
Balcony
$1,902
Suite
$2,162
From
US$1,052
Save 546
Per Person
View Trip
8 Day 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 Epic
Departures: Dec 2025 to Apr 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados, Saint Lucia, Sint Maarten
Exclusive Savings
Inside
$639
Oceanview
-
Balcony
-
Suite
$3,743
From
US$639
Save 202
Per Person
View Trip
8 Day Southern Caribbean Holiday with Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departures: Nov 2027 to Dec 2027
Visit: Puerto Rico, Dominica, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$534
Oceanview
$584
Balcony
$859
Suite
$2,559
From
US$534
Save 524
Per Person
View Trip
8 Day Lesser Antilles: Valentine's Day with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 13 February 2027
Visit: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
With Love From the World
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$4,130
From
US$1,043
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
$706
Balcony
$969
Suite
-
From
US$706
Per Person
View Trip
22 Day From the Caribbean to the Amazon with Viking Cruises
Cruise
 (5)

22 Days (21 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 15 December 2026
Visit: Puerto Rico, Barbados, French Guiana, Brazil (+4 more), Trinidad and Tobago, Saint Lucia, Antigua and Barbuda, Virgin Islands
Viking $799 Air Deal
Inside
-
Oceanview
-
Balcony
$11,499
Suite
-
From
US$11,499
Per Person
View Trip
8 Day Southern Caribbean Cruise 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
Departure: 03 January 2027
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao
Inside
$1,579
Oceanview
-
Balcony
$1,829
Suite
$3,083
From
US$1,579
Per Person
View Trip
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 17 January 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Montserrat, Antigua and Barbuda, Guadeloupe
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$61,421
From
US$61,421
Save 1,859
Per Person
View Trip
8 Day Antiguan Elegance & Sunny St. Isles 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
With Love From the World
Inside
$973
Oceanview
$1,113
Balcony
$1,323
Suite
$4,130
From
US$973
Per Person
View Trip
16 Day An Extended Journey Of Caribbean Inspiration And Island Beauty with Explora Journeys
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 January 2026
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Antigua and Barbuda (+6 more), Anguilla, USA, Guadeloupe, Barbados, Martinique, Saint Kitts and Nevis
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
-
Suite
$14,150
From
US$14,150
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
With Love From the World
Inside
$1,043
Oceanview
$1,253
Balcony
$1,404
Suite
$3,010
From
US$1,043
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: 22 March 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica, Barbados, Grenada
Princess Plus
Princess Premier
Inside
$1,283
Oceanview
$1,353
Balcony
$2,263
Suite
$2,973
From
US$1,283
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: 02 May 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Dominica
Exclusive Savings
Inside
$660
Oceanview
$700
Balcony
$1,792
Suite
$1,723
From
US$660
Save 431
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
Departures: Mar 2026 to Mar 2026
Visit: Puerto Rico, Virgin Islands, Curacao, Aruba, Bonaire
Exclusive Savings
Inside
$698
Oceanview
$718
Balcony
$1,076
Suite
$1,998
From
US$698
Save 494
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
Exclusive Savings
Inside
$779
Oceanview
$840
Balcony
$1,499
Suite
$1,679
From
US$779
Save 495
Per Person
View Trip
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