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Puerto Rico Cruises Starting In September 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in September 2027 or 2028, we have 12 unique cruise itineraries and 103 departures available, operated by five of the world's leading cruise lines departing in September.
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12 Cruises (103 Departures)
12 Cruises (103 Departures)
Departures
Duration
4 Days
10 Days
Start & End Cities
Ship Size
Ship Features
Operators
Price
$700pp
$28,620pp
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
$1,569
Oceanview
-
Balcony
$1,680
Suite
$2,386
From (Per Person)
A$1,569
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Sep 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$952
Oceanview
$1,249
Balcony
$1,556
Suite
$2,309
From (Per Person)
A$952
Save 16
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
$1,302
Oceanview
$1,592
Balcony
$1,558
Suite
$3,401
From (Per Person)
A$1,302
Save 1,214
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
$6,366
Suite
$8,306
From (Per Person)
A$6,366
Save 113
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
$863
Oceanview
-
Balcony
$1,953
Suite
-
From (Per Person)
A$863
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
$1,103
Oceanview
$1,228
Balcony
$1,664
Suite
$4,051
From (Per Person)
A$1,103
Save 1,202
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
$892
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$892
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 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
$1,011
Oceanview
$1,193
Balcony
$1,557
Suite
$2,141
From (Per Person)
A$1,095
Save 655
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
$1,019
Oceanview
$1,108
Balcony
$1,689
Suite
$2,307
From (Per Person)
A$1,067
Save 906
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: Sep 2026 to Oct 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,331
Oceanview
$1,692
Balcony
$2,027
Suite
$4,151
From (Per Person)
A$1,331
Save 963
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: 12 results

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