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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 15 unique cruise itineraries and 116 departures available, operated by five of the world's leading cruise lines departing in September.
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15 Cruises (116 Departures)
15 Cruises (116 Departures)
Departures
Duration
4 Days
15 Days
Start & End Cities
Ship Size
Ship Features
Operators
Price
$800pp
$28,480pp
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
Cruise Line: 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
$1,924
From (Per Person)
A$1,508
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: Aug 2026 to Oct 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,899
Oceanview
$2,041
Balcony
$2,113
Suite
$4,472
From (Per Person)
A$1,899
Save 1,121
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
Visits: Canada, Bermuda, Puerto Rico, Aruba
Exclusive Savings
Balcony
$4,690
Suite
$6,719
From (Per Person)
A$4,690
Save 79
Per Person
View Trip
4 Day San Juan to Bridgetown with Crystal Cruises
New ReleaseCruise

4 Days (3 Nights) San Juan to Bridgetown
Cruise Line: Crystal
Ship: Crystal Symphony
Departure: 14 September 2026
Visits: Puerto Rico, Saint Martin, Dominica, Barbados
Exclusive Savings
Oceanview
$1,980
Balcony
$2,640
Suite
$2,850
From (Per Person)
A$1,980
Save 420
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: Sep 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,607
Suite
$2,755
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
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,229
Oceanview
$1,527
Balcony
$2,141
Suite
$4,575
From (Per Person)
A$1,229
Save 769
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: Aug 2026 to Sep 2026
Visits: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$894
Oceanview
$904
Balcony
$1,340
Suite
$2,221
From (Per Person)
A$894
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
Visits: USA, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,370
Oceanview
$1,578
Balcony
$1,449
Suite
$3,426
From (Per Person)
A$1,689
Save 781
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: Aug 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,051
Oceanview
$1,289
Balcony
$1,586
Suite
$2,309
From (Per Person)
A$1,051
Save 23
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
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,101
Oceanview
$1,144
Balcony
$1,834
Suite
$2,319
From (Per Person)
A$1,276
Save 622
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
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,053
Oceanview
$1,094
Balcony
$1,598
Suite
$2,629
From (Per Person)
A$1,505
Save 185
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: Aug 2026 to Oct 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,468
Oceanview
$1,707
Balcony
$1,702
Suite
$4,176
From (Per Person)
A$1,468
Save 655
Per Person
View Trip
10 Day Guayaquil to San Juan with Crystal Cruises
New ReleaseCruise

10 Days (9 Nights) Guayaquil to San Juan
Cruise Line: Crystal
Ship: Crystal Symphony
Departure: 05 September 2026
Visits: Ecuador, Panama, Colombia, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$6,500
Balcony
$8,600
Suite
$9,050
From (Per Person)
A$6,500
Save 900
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
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$1,509
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$1,509
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
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Exclusive Savings
Inside
$1,690
Oceanview
-
Balcony
$2,898
Suite
$4,476
From (Per Person)
A$1,690
Per Person
View Trip
Results: 15 results

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