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Puerto Rico Cruises Starting In September 2026, 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in September 2026, 2027 or 2028, we have 14 unique cruise itineraries and 108 departures available, operated by four of the world's leading cruise lines departing in September.
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15 Days
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14 Cruises (108 Cruise Departures)
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Sep 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin
Princess Standard
Exclusive Savings
Inside
$1,211
Oceanview
-
Balcony
$1,223
Suite
$1,617
From
A$1,211
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: Jul 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,829
Oceanview
$2,009
Balcony
$2,066
Suite
$3,207
From
A$1,829
Save 1,301
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,219
Oceanview
$1,601
Balcony
$1,988
Suite
$5,432
From
A$1,219
Save 711
Per Person
View Trip
9 Day Atlantic Crossing: Halifax To Bermuda & Puerto Rico with Seabourn
Cruise

9 Days (8 Nights) Halifax to Oranjestad
Cruise Line: Seabourn
Ship: Seabourn Pursuit
Departure: 24 September 2028
Visit: Canada, Bermuda, Puerto Rico, Aruba
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,209
Suite
$7,463
From
A$5,209
Save 90
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Exclusive Savings
Inside
$894
Oceanview
$904
Balcony
$1,340
Suite
$1,686
From
A$894
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Jun 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,133
Oceanview
$1,371
Balcony
$1,658
Suite
$2,302
From
A$1,133
Save 21
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: Nov 2026 to Sep 2027
Visit: USA, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,390
Oceanview
$1,537
Balcony
$1,585
Suite
$3,475
From
A$1,390
Save 1,262
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,676
Suite
$2,023
From
A$865
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 06 September 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Exclusive Savings
Inside
$1,690
Oceanview
$1,852
Balcony
$3,349
Suite
-
From
A$1,690
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
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,101
Oceanview
$1,203
Balcony
$1,834
Suite
$2,446
From
A$1,101
Save 903
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: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$966
Oceanview
$1,117
Balcony
$1,624
Suite
$2,602
From
A$966
Save 815
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Sep 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Exclusive Savings
Inside
$1,473
Oceanview
$1,641
Balcony
$3,446
Suite
-
From
A$1,473
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Jun 2026 to Oct 2027
Visit: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,451
Oceanview
$1,665
Balcony
$1,631
Suite
$4,543
From
A$1,451
Save 1,163
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 27 September 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Princess Standard
Exclusive Savings
Inside
$1,690
Oceanview
$1,752
Balcony
-
Suite
-
From
A$1,690
Per Person
View Trip
Results: 14 results

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