Italy help, please

[Jo]

I’m really having trouble making decisions and need to solve this fast.. 

we fly into Milan on July 4, out of Rome on the 14th. 

Ive booked one night in Milan (we want to see the cathedral and downtown), and 4 nights in Rome. I have 5 nights in the middle that I haven’t booked yet - oops. 

We we were planning for 5 nights near Lake Como but I don’t think that’s the region we really want. And I don’t know Italy as well as other European countries.

do we want Tuscany? Or Umbria? One friend recommended Orvieto, another suggested Siena. I’m finding lots of places within our budget on VRBO, I just can’t seem to focus on one town or area.

we are a family of 4, kids are 9 and 13, and we want a place where we can relax with some sorts of views of countryside or town, but also relatively good proximity to sights and interesting places to visit. 

We plan to rent a car and dh and I have visited Rome and Florence before, but it’s the kids’ first time in Italy so we want to be able to see and do some of the major things.

what region would you recommend? And are there specific towns within there that would be good for us? Thanks!

[jenandjeh]

One of my favorite trips was when some girlfriends and I stayed in Lucca. That town was amazing and so friendly. There is a train station and it's an easy train ride to Florence where we spent a full day, the next day we trained from Lucca to La Spezia and then on to Cinque Terre which was amazing and I could have spend multiple days exploring those tiny towns and on the final day, we trained to Pisa and spent the day in Pisa.

[marytini]

Tuscany isn't a bad idea. You could stay near Siena and visit the various hill towns each day. Could train into Florence one day too if you want to take the kids there.
I've never been to Lucca, but I think you can bike around the city walls there. Kids might like that.

[Jo]

Thank you both. I’ve been searching and have narrowed it down to a villa in Tuscany about 15 miles outside of Siena or an apartment in central Florence.

I couldn’t find anything in the smaller towns that would work for us, but I’m pretty happy with the current options. We plan to visit Lucca, San Gimignano, Siena and Florence.

[clseale]

Jun 16, 2019 7:31:36 GMT -5 Jo said:

Thank you both. I’ve been searching and have narrowed it down to a villa in Tuscany about 15 miles outside of Siena or an apartment in central Florence.

I couldn’t find anything in the smaller towns that would work for us, but I’m pretty happy with the current options. We plan to visit Lucca, San Gimignano, Siena and Florence.

We had a lovely lunch & wine tasting here:
fattoriapoggioalloro.com/

We had fun touring the farm, then enjoyed lunch and wine with gorgeous views of San Gimignano.