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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)
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
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
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Lucia, Antigua and Barbuda, Saint Martin
Exclusive Savings
Inside
$1,076
Oceanview
$1,126
Balcony
$1,551
Suite
$3,782
From
US$1,076
Save 675
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 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: Feb 2026 to Apr 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados, Saint Lucia, Sint Maarten
Exclusive Savings
Inside
$689
Oceanview
-
Balcony
$1,119
Suite
$1,299
From
US$689
Save 136
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
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 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
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: 26 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Montserrat
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,840
Balcony
$4,480
Suite
$7,640
From
US$3,840
Save 960
Per Person
View Trip
8 Day Southern Caribbean with Barbados Holiday with Princess
Cruise
 (6)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Princess Standard
Inside
$1,326
Oceanview
$1,476
Balcony
$2,001
Suite
$2,441
From
US$1,326
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, Antigua & Barbados with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 21 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+9 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Saint Barthelemy
Azamara Always Included
Exclusive Savings
Inside
$3,599
Oceanview
$3,773
Balcony
$4,869
Suite
$7,556
From
US$3,599
Save 80
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
$708
Oceanview
$729
Balcony
$919
Suite
$1,878
From
US$708
Save 399
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 Viva
Departure: 23 January 2028
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Bonaire, Curacao
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,447
From
US$1,169
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
$1,709
Oceanview
$1,959
Balcony
$2,709
Suite
$3,207
From
US$1,709
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
Inside
$973
Oceanview
$1,113
Balcony
$1,323
Suite
$3,493
From
US$973
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
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$4,130
From
US$1,043
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
Inside
-
Oceanview
$1,372
Balcony
-
Suite
-
From
US$1,372
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: 14 November 2026
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Saint Kitts and Nevis, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$589
Oceanview
$659
Balcony
$1,459
Suite
$1,601
From
US$589
Save 361
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: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,520
Balcony
$4,320
Suite
$8,500
From
US$3,520
Save 880
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 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
11 Day A Journey Into Historic Charm & Tropical Bliss with Explora Journeys
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 February 2026
Visit: Puerto Rico, Aruba, Curacao, Bonaire (+4 more), Barbados, Guadeloupe, Saint Martin, Virgin Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,495
Suite
$6,195
From
US$5,495
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: 07 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+4 more), Dominica, Barbados, Saint Kitts and Nevis, Grenada
Princess Standard
Inside
$1,426
Oceanview
$1,676
Balcony
$2,426
Suite
$3,126
From
US$1,426
Per Person
View Trip
10 Day Southern Caribbean Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 29 October 2027
Visit: Puerto Rico, Antigua and Barbuda, Saint Lucia, Grenada, Barbados, Saint Vincent, Virgin Islands
Exclusive Savings
Inside
$930
Oceanview
$980
Balcony
$1,255
Suite
$3,297
From
US$930
Save 591
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
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
9 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 31 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda, Saint Vincent
Bonus Onboard Credit
Exclusive Savings
Inside
$1,410
Oceanview
$1,601
Balcony
$2,720
Suite
$2,948
From
US$1,410
Save 701
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 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
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
16 Day An Extended Journey into Island Bliss & Lively Celebrations with Explora Journeys
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Saint Barthelemy, Anguilla, USA, Dominican Republic
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$9,600
Suite
$10,835
From
US$9,600
Per Person
View Trip
Results: 91-120 of 147

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