50th birthday in Tuscany June 2020


New member
I am hoping I can get some ideas.....
My dream birthday is renting a big house for a week with swimming pool etc for a week with friends, Ideally in a village or close by to walk to a village ( so as not to drive everywhere)... somewhere there are nice things to do and sightsee. (eg wineries, art galleries etc) and either have a catered lunch at the home or in a winery for my actual birthday celebration. I have only been to Florence for a week and a day trip to Chianti which was just gorgeous. There are so many beautiful areas and I'm getting a little overwhelmed with where I should be looking. I'm thinking somewhere between Florence and Pisa would be good but also the coast would be nice too....I would love some suggestions please.... thank you in advance :)


The Tuscan Expert ;-)
Staff member
For a trip in 2020 you are definitely planning in advance! :D It's a good thing, particularly when looking at renting large villas for groups since those definitely have to be booked ahead of time before they start breaking up the time periods they have available.

How many people total are you looking to have at the villa for sleeping? I ask because there are all sizes, and it changes the recommendations I give you.

My first suggestion would place you near Florence but outside the city in the countryside with views of the city, and close enough to a small town so that you could walk there when you wanted to:
It gives you a taste of the countryside They have great views of Florence from up there! They have several apartments of various sizes which you could rent to increase the number of people as well as a separate villa with its own pool, which can host up to 12.

Another good option would be Torre a Cona: https//:www.visitflorence.com/villas-near-florence/torre-a-cona.html
which is another wine estate that offers apartments and 2 villas, which can host up to 12 or 16 guests.

Being wineries, they offer the chance to have tastings, visits to the cellars and cooking experiences as well as the possibility to cater your party directly there.

Other good options, not knowing how big you want them to be:

Villa di Cabbiavoli: http://www.tuscanyaccommodation.com/villa-di-cabbiavoli.html

Villa Vianci: http://www.tuscanyaccommodation.com/villa-vianci.html

Villa Piaggia: http://www.tuscanyaccommodation.com/villa-piaggia.html

Ok, if these are not the right size or what you were looking for, let me know more details so I can offer other alternatives!


New member
Oh these suggestions are great - thank you so much!!
They are definitely the type of places and in the area I'm thinking of. I am not entirely sure how many friends might come at this early stage but probably about 12.
I shall look more closely at the information you have provided - thanks again, you are so helpful!
Helen :)