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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 113 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 (113 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 to Sep 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin
Princess Standard
Inside
$719
Oceanview
-
Balcony
$769
Suite
$929
From
US$719
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
$647
Oceanview
$980
Balcony
$1,315
Suite
$2,437
From
US$647
Save 460
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
Inside
$1,210
Oceanview
-
Balcony
-
Suite
-
From
US$1,210
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
$571
Oceanview
$621
Balcony
$956
Suite
$1,199
From
US$571
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
Bonus Onboard Credit
Exclusive Savings
Inside
$759
Oceanview
$1,094
Balcony
$1,106
Suite
$2,205
From
US$759
Save 798
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: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$567
Oceanview
$763
Balcony
$897
Suite
$1,444
From
US$567
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
Inside
-
Oceanview
-
Balcony
$3,499
Suite
$4,999
From
US$3,499
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: Jun 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$579
Oceanview
$599
Balcony
$874
Suite
$1,089
From
US$579
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: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,193
Oceanview
$1,544
Balcony
$1,609
Suite
$2,955
From
US$1,193
Save 933
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
$598
Oceanview
$750
Balcony
$1,149
Suite
$1,604
From
US$598
Save 555
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
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,473
From
US$674
Save 571
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
Bonus Onboard Credit
Exclusive Savings
Inside
$874
Oceanview
$989
Balcony
$1,056
Suite
$2,917
From
US$874
Save 750
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
Inside
$1,088
Oceanview
$1,226
Balcony
-
Suite
-
From
US$1,088
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
$1,310
Oceanview
$1,308
Balcony
$2,542
Suite
-
From
US$1,308
Per Person
View Trip
Results: 14 results

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