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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 110 departures available, operated by five of the world's leading cruise lines departing in September.
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14 Cruises (110 Departures)
14 Cruises (110 Departures)
Departures
Duration
4 Days
15 Days
Start & End Cities
Ship Size
Ship Features
Operators
Price
$800pp
$30,840pp
Countries
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8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Regal Princess
Departures: Sep 2026
Visits: USA, Dominican Republic, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,508
Oceanview
-
Balcony
$1,571
Suite
$2,583
From (Per Person)
A$1,508
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC World America
Departures: Aug 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,002
Oceanview
$1,338
Balcony
$1,655
Suite
$2,309
From (Per Person)
A$1,002
Save 24
Per Person
View Trip
9 Day Atlantic Crossing: Halifax To Bermuda & Puerto Rico with Seabourn
Cruise

9 Days (8 Nights) Halifax to Oranjestad
Operator: Seabourn
Ship: Seabourn Pursuit
Departure: 24 September 2028
Visits: Canada, Bermuda, Puerto Rico, Aruba
Exclusive Savings
Balcony
$4,514
Suite
$6,366
From (Per Person)
A$4,514
Save 75
Per Person
View Trip
4 Day San Juan to Bridgetown with Crystal Cruises
New ReleaseCruise

4 Days (3 Nights) San Juan to Bridgetown
Operator: Crystal
Ship: Crystal Symphony
Departure: 14 September 2026
Visits: Puerto Rico, Saint Martin, Dominica, Barbados
Exclusive Savings
Oceanview
$2,347
Balcony
$2,835
Suite
$3,030
From (Per Person)
A$2,347
Save 53
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Star Of The Seas
Departures: Aug 2026 to Oct 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,783
Oceanview
$1,923
Balcony
$2,190
Suite
$4,398
From (Per Person)
A$1,783
Save 1,255
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departures: Nov 2026 to Sep 2027
Visits: USA, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,461
Oceanview
$1,578
Balcony
$1,584
Suite
$3,070
From (Per Person)
A$1,461
Save 1,276
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ship: Caribbean Princess
Departure: 06 September 2026
Visits: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$894
Oceanview
$918
Balcony
$1,457
Suite
$2,311
From (Per Person)
A$894
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ship: Caribbean Princess
Departures: Sep 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,750
Suite
$3,607
From (Per Person)
A$865
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,355
Oceanview
$1,527
Balcony
$1,900
Suite
$4,614
From (Per Person)
A$1,355
Save 794
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,060
Oceanview
$1,144
Balcony
$1,598
Suite
$2,721
From (Per Person)
A$1,060
Save 679
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,052
Oceanview
$1,092
Balcony
$1,834
Suite
$2,245
From (Per Person)
A$1,052
Save 869
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Aug 2026 to Oct 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,468
Oceanview
$1,665
Balcony
$1,726
Suite
$4,102
From (Per Person)
A$1,468
Save 963
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Operator: Princess
Ship: Caribbean Princess
Departure: 27 September 2026
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Exclusive Savings
Inside
$1,651
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$1,651
Per Person
View Trip
10 Day Guayaquil to San Juan with Crystal Cruises
New ReleaseCruise

10 Days (9 Nights) Guayaquil to San Juan
Operator: Crystal
Ship: Crystal Symphony
Departure: 05 September 2026
Visits: Ecuador, Panama, Colombia, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$6,275
Balcony
$7,445
Suite
$7,932
From (Per Person)
A$6,275
Save 1,125
Per Person
View Trip
Results: 14 results

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