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Puerto Rico Cruises Starting In September 2026 and 2027

If you're looking at joining a cruise to Puerto Rico in September 2026 or 2027, we have 12 unique cruise itineraries and 118 departures available, operated by three of the world's leading cruise lines departing in September.
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12 Cruises (118 Cruise Departures)
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,343
Oceanview
$1,524
Balcony
$1,711
Suite
$3,381
From
US$1,343
Save 883
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: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$597
Oceanview
$853
Balcony
$914
Suite
$1,410
From
US$597
Per Person
View Trip
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 to Sep 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin
Princess Standard
Inside
$574
Oceanview
-
Balcony
$749
Suite
$1,029
From
US$574
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
Departures: Jul 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$940
Oceanview
$1,155
Balcony
$1,410
Suite
$1,720
From
US$940
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
$877
Oceanview
$1,098
Balcony
$1,440
Suite
$2,290
From
US$938
Save 493
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: May 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$474
Oceanview
$534
Balcony
$599
Suite
$879
From
US$474
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
Inside
$486
Oceanview
$536
Balcony
$691
Suite
$811
From
US$486
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departures: Jun 2026 to Sep 2026
Visit: USA, Saint Kitts and Nevis, Sint Maarten, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,023
Oceanview
$1,136
Balcony
$1,178
Suite
$2,888
From
US$1,023
Save 746
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
$540
Oceanview
$580
Balcony
$1,393
Suite
$1,409
From
US$540
Save 353
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: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$978
Oceanview
$1,068
Balcony
$1,418
Suite
$1,608
From
US$978
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
Bonus Onboard Credit
Exclusive Savings
Inside
$801
Oceanview
$881
Balcony
$1,398
Suite
$1,898
From
US$801
Save 455
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
Inside
$950
Oceanview
$1,090
Balcony
$1,540
Suite
$1,840
From
US$950
Per Person
View Trip
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