Two families with teens - need suggestion on accommodation and city

My sisters family and my family will meet in ITALY this July to celebrate her birthday. Our kids range from 12-16 (5 total) There will be 5 adults. A villa with a pool for 10 people is our wish. We ultimately would like a place that has a town close by to walk to and several other towns to drive for day tours. The plan is that we could return home most nights for dinner that we can cook ourselves and relax in with some nice wine finds from the days excursions. Too tall an expectation? We are very flexible as to the city. Thanks for any suggestions.
 
Hello Therese and welcome to the Forum!

I don't think your expectations are too tall, you just need to find the perfect accommodation for your needs! :)

I've made a research to find some good suggestions and these are the results:

Villa Vinci ( http://www.tuscanyaccommodation.com/villa-vianci.html ) is charming villa with pool in Chianti, only 8 km from Siena. It has 6 rooms and a fully equipped modern kitchen.

Fattoria il Lago (http://www.tuscanyaccommodation.com/fattoria-il-lago.html) is a large farmhouse in Mugello, in North Florence. It has a very nice villa for up to 12 guests.

Villa La Medicea (http://www.tuscanyaccommodation.com/villa-la-medicea.html) has 2 apartments and a pool an is located in the Florence surroundings.

Villa Piaggia (http://www.tuscanyaccommodation.com/villa-piaggia.html) near San Gimignano and Villa Cabbiavoli in the Chianti countryside (http://www.tuscanyaccommodation.com/villa-di-cabbiavoli.html) have luxurious comforts.
 
My sisters family and my family will meet in ITALY this July to celebrate her birthday. Our kids range from 12-16 (5 total) There will be 5 adults. A villa with a pool for 10 people is our wish. We ultimately would like a place that has a town close by to walk to and several other towns to drive for day tours. The plan is that we could return home most nights for dinner that we can cook ourselves and relax in with some nice wine finds from the days excursions. Too tall an expectation? We are very flexible as to the city. Thanks for any suggestions.

I think with teen ones we also developed strategies, many the same, but the big one was starting very early morning to avoid traffic and food stops and minimize journey time.
 
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