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Need help planning our stay in Cortona

We are planning on going to Italy the end of Aug./early Sep. We have a place for one week in Cortona, we want to extend our stay by 3 or 4 more nights. Would like to spend some time on the Italian Riviera, perhaps Cinque Terre. We are not sure if we need to stay some nights in Rome or Florence or can we see enough by doing day trips from Cortona? This will be our 1st trip to Italy. We would appreciate advice to help us plan our vacation.

Posted by
8 posts

HI Steve,
Thanks for your suggestions, we purchased from a benefit auction 7 nights in Cortona. Now that we have began planning our trip we are wishing we would not have done that knowing that we want to see so much more. What would you think if we had an itinerary something like this: fly into Rome spend 2 nights in CT then 1 or 2 nights in Florence then 6 nights in Cortona ending with 2 nights in Rome? I would appreciate any suggestions you might have. Thank you so much.

Posted by
1449 posts

Actually I think the auction has done you a favor. Rather than rushing around trying to see it all like many 1st-time visitors do, why not take what you have and enjoy it? With the advance time you have you can look into cooking classes in the Tuscany/Umbria area, find wineries to visit, plan a day trip to Florence and Siena. There a lots of hilltowns to visit in the area that are accessible via public transit or more conveniently with a car. Spello, Spoleto, Arezzo, Assisi, crafts in Deruta, to name a few. And there is a hotel/restaurant with an incredible view out the back deck right at the entrance to old-town Cortona where you can relax and watch the sun set over the fields in the valley below.

If you want to go to Rome, I'd suggest you add on to your trip a few days and take the train into Termini station.

Posted by
787 posts

If you want to start your trip with 2 nights in the Cinque Terre, then flying into Milan would make more sense.

And I'd probably cut some of your time in Cortona (even though it's already paid for), and add those days to all of your other destinations. Keep in mind that 2 nights in Rome, or the Cinque Terre, or Florence, actually means one full day plus some time - and that's not much time in any of those wonderful locations!

Another option: Plan to return to Italy and visit Rome then. On this trip, focus further north, and plan to spent time in the Cinque Terre and Florence.

Keep in mind, too, that August is the BIG vacation month for Italians (especially the last half of the month), so there will be big crowds in places such as the Cinque Terre (in fact, you might want to put your time there at the end of your trip), and many restaurants will be closed. All the attractions and museums should still be open, though.

Posted by
8 posts

Thanks, for all of the suggestions. I didn't realize that Aug. would be a busier time. I'm not locked into any certain dates to travel, I think we should push it out to the later part of September? Do I need to worry about the weather in late Sep.? So much to think about!

Posted by
400 posts

You're right Trish, there is a lot to consider. Sept. is a wonderful month to travel in Italy...really better - not so many tourists and not as hot. I would definitely change if you can. Don't give up your stay in Cortona. Fly into Florence and take the train to CT. Stay for a few days...you will absolutely love it there! Take train to Cortona for your stay there and day trip to Florence and nearby hilltowns...easy by train. Then take train to Rome for at least 3 days. If you still have an extra day, stop in Orvieto on your way to Rome and must stay overnight or 2..love it there too. Fly home from Rome after your stay there. None of your train rides will be longer than 3 hrs or less.
Good luck!