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Traveling with my parents to a villa in Cortona Italy

Posted by (Corvallis Oregon ) on

Greetings all,

In mid April 2026 I get a surprise visit to Italy! I've been taking a long time to plan a trip to Liguria and then my parents say, "Yes," to a Cortona opportunity. Wow!

So now my questions turn to Tuscany. First off, I'd like insights and advice flying from Portland OR or Seattle WA into Tuscany.

It looks like flights could be less expensive from PDX. Is it easier to fly into Rome or Florence? And, how have any of you handled round trip flights or finagling flying into one city & leaving from another? Can two one trip tickets be more economical? Or just a pain?

Any airline recommendations?

Further, how about the train ride from either city to the train station near Cortona?

I can look at what it takes on paper, well, a screen, but I come here to learn what others have learned.

My thanks,

Kristin :)

Posted by
16722 posts

Cortona is in the province of Arezzo, so about half way between Florence and Rome (but a bit closer to Florence). You can fly to either but for now there are no non stop flights to either city from PDX or SEA (I don’t know in 2026), therefore you will need a layover somewhere else in Europe. You can choose the option that best suits your needs. If you want to fly to a city and return from another, you would choose a multi city flight (see Google Flights or Kayak) for example PDX - FLR going and FCO - PDX returning.
If you rent a villa in Cortona you will likely need a rental car, which you can get in either Florence or Rome. If you want to minimize driving, there is also the option of renting in Arezzo or Chiusi since Avis Budget is present in both cities near the station (Arezzo is north of Cortona, while Chiusi is south of it.

Posted by
12666 posts

Alaska Airlines begins Seattle -Rome flights in May 2026, perhaps that could be useful for the trip home?

Can two one trip tickets be more economical?

Probably not; just plug in your projected flying dates and compare. You can also look at 'multi-city' ( aka open jaw) flights as well as round trip offerings.

Posted by
561 posts

I see you live in Corvallis. You may be able to begin your trip in Eugene; I don't know how frequent the flights are or how much more it would cost compared to driving to (and parking at) PDX or SEA. But it is another option to consider. Personally I prefer to fly from PDX, but Seattle does have more flights to choose from. (Surprisingly, it is often less expensive to fly from PDX than it is from SEA.) Google Flights will be very helpful to you! Choose "Multi City" so you don't have to backtrack at the end of your trip. You can set multiple alerts to check prices on different routes and days. I believe Alaska Air's flights to/from Rome will be available for booking in September.

For Florence/Cortona, you may want to consider flying into Bologna. It's an easy-to-navigate airport: you can take the Marconi Express from the airport to Bologna Centrale station. From there multiple trains go to Florence and onward to Cortona.

Speaking of trains, the Seat 61 website is very helpful and explains train travel in Italy.

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