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Need advice planning 10 days in September

My wife and I are visiting Italy for 10 days in September. It's my second trip... I've already seen Venice and Florence and would prefer to see other areas.

We are flying into Rome and spending 5 nights there. That's definite. Our next 6 nights are still up in the air.

I would like to go to Cinque Terre, but have not been able to find availability at any nice places yet.

Another option is to visit somewhere in Tuscany for a few nights, but then I'm not sure where to go after that. Or maybe we just do two locations: Rome and Somewhere Else.

I like the idea of a small town like Montalcino, but I am worried that there won't be enough for 4 or 5 days there.

I like the idea of staying at an agriturismo but it seems limiting as far as breakfast and dinner options since there would be little nearby (we are looking at Fattoria Tregole near Castellina in Chianti).

I currently have a reservation at a hotel by the Milan airport for our last night since we have an early flight home.

The current plan works but it is four hotels in 11 nights - seems like too much moving around.

Here's our itinerary. Any advice would be helpful!

(Cinque Terre is still a maybe because I haven't found a hotel yet).

http://grab.by/5OUf

Posted by
817 posts

What do you and your wife like to do on vacation, or what would you like to do in Italy? Art, museums, culture, people-watching, wine-tasting, hiking? Your interests should effect what your eventual itinerary will be.

One comment on your current plan is that if you visit the Cinque Terre, you're only spending 1+ day in Tuscany. Maybe, if you do go to Tuscany, cut one day from the Cinque Terre and add it to Tuscany. Did you check with Villa Steno in Monterosso, to see if they have availability?

Montalcino is a nice little town, especially if you enjoy Brunello! I think there's enough in the vicinity to spend 4-5 days there (again, depending on your interests). You could take day trips to Pienza, Montepulciano, San Quirico d'Orcia, Siena, San Gimignano, Volterra, Monteriggioni, even Orvieto if you want, as well as wine tastings at large or small wineries in the area.

Another comment. We made more than several trips to Italy, flying into Milan, but never visited Milan. Then we had to visit Milan, as my husband had a business meeting there. I was delighted with the city! Not too touristy, great people-watching, and several very nice smaller museums with world-class art. Of course the very famous "Last Supper" and the cathedral were both amazing. And I was relieved to see that not everyone there dresses like a fashionista. So if all that appeals to you, consider spending a day in Milan.

We prefer staying in towns rather than agriturismos. In town, you can walk to dinner & have wine without worrying about driving afterward, and you have a choice of restaurants and cafes and gelaterias.