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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 119 departures available, operated by five of the world's leading cruise lines departing in September.
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14 Cruises (119 Departures)
14 Cruises (119 Departures)
Departures
Duration
4 Days
15 Days
Start & End Cities
Ship Size
Ship Features
Operators
Price
$700pp
$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
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: Aug 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,750
Suite
$2,182
From (Per Person)
A$865
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
$5,209
Suite
$7,463
From (Per Person)
A$5,209
Save 90
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
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,908
Oceanview
$2,136
Balcony
$2,192
Suite
$3,695
From (Per Person)
A$1,908
Save 2,172
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
Visits: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$894
Oceanview
$904
Balcony
$1,340
Suite
$1,686
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
$1,380
Oceanview
$1,615
Balcony
$1,514
Suite
$3,401
From (Per Person)
A$1,380
Save 1,216
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
$1,170
Oceanview
$1,527
Balcony
$1,944
Suite
$3,807
From (Per Person)
A$1,170
Save 701
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: Jul 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$982
Oceanview
$1,220
Balcony
$1,517
Suite
$2,309
From (Per Person)
A$982
Save 22
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
$1,030
Oceanview
$1,137
Balcony
$1,594
Suite
$2,574
From (Per Person)
A$1,030
Save 701
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
$1,203
Balcony
$1,834
Suite
$2,294
From (Per Person)
A$1,101
Save 1,074
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
-
Suite
$4,476
From (Per Person)
A$1,690
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
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
$1,401
Oceanview
$1,805
Balcony
$1,774
Suite
$4,151
From (Per Person)
A$1,401
Save 963
Per Person
View Trip
Results: 14 results

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