Best place to stay in Tuscany?

One of my favorite Tuscan towns is Cortona.  It is just the right size to maintain its charm and still have a few good options for drinks, dinner and meandering up winding alleys or through shops. Cortona is perched on top of one of Tuscany's famous hills giving it views from almost every point. Also there is a really nice park that runs along a ridge that is very relaxing to take a stroll in, it even has an outdoor theater connected to it. The main shopping road is Via Nazionale and if you happen to be there on a Saturday there is a market in Piazza Signorelli.

As for the hotel, if you must have a pool I would say the Relais Corte Dei Papi. the only true draw back to this hotel is that its outside the town; but there is a bus and taxis if they are needed.

If you wouldn't mind using the community pool (just look for the sign reading "Piscina") I would say the 18th century converted residence Villa Marsili is they way to go. It provides you with nice onsite amenities, but also allows you to enjoy all the charm of the town.

If you are using the train system to get around Italy, Cortona has its own stop, which makes it easily reached.

Thanks,

Travelationship.com

I would love to list off a list of amazing places, but instead, I will warn you against the filthy, bug-infested "villa" that we escaped from after just one night in mildewed torn-up sheets.

Agriturismo Diacceroni.

It's on Homeaway.com. The reviews and summer photographs look amazing. But we were there and it was absolutely horrifying.

I do recommend doing a quick search for driving times on Google or Mapquest when you start looking for these amazing Italian villas. Many are tucked away in the hills which is picturesque, but you may be spending 30 minutes on very curvy country roads just to find a main road which is ok, but it's good to know up front what you're getting yourself into.

Forte dei Marmi is a cool town right off the coast...very Italian with very little tourists. So, a true experience. From there, you are a short bike ride to Pietrasanta, another cool little town with an authentic experience. Also, a short train ride to Cinque Terre, with five awesome towns right on the water. If you go, make it to the last town on the rail --  Monterosso - Cinque Terre and take the long walk up the stairs to the world's coolest convent and most amazing view in Italy. 

Hullo Hayley, good evening, I am running an agriturismo near Volterra, it is called Agriturismo Fattoria di Statiano and we produce wine in Micciano. we would love to have you at the farm! But mostly, i real reccomand to visit this part of Tuscany that is off the beaten tracks, really and authentic spot! Nearby there are really stunning little village on the top of rolling hills like for example Montegemoli and Querceto

We stayed at a tiny Bed and Breakfast in a town that is barely on the map - called Vico D'Elsa. The B&B is called La Volpaia and the original home was built in the 1500's and the owners are an eccentric artist who loves to discuss politics over wine in the evening and his amazing chef of a wife. The closest "big" town is San Gimignano. It is the perfect launching pad for a day in Florence, Lucca, and SG. You must rent a car though. It is truly paradise. http://www.lavolpaia.it/

I stayed twice at La Gemma bed and breakfast. It is situated in Lucca. This is a beautiful town some km far from Florence. There are some interesting things to see there. Moreover, Lucca isn't a touristy place. This is a bonus in my opinion.

About the bed and breakfast, La Gemma is a basic accomodation, but it is a nice place. I wrote a review on Travbuddy.com

Ciao!

In my opinion the  best place to stay is the Paradù Tuscany EcoResort. Really nice there!

Hi Laura,

when I spend a weekend out of town (I live in Florence at the moment) I usually go to Montecatini Terme, because of its hot springs. Tuscany is famous in Italy for pools of natural thermal water, while usually turists are not aware of this! Such a pity, everybody has to know! Last time I was in Ercolini & Savi hotel, a nice and classic hotel in the center and had a great time.

Another time I was in Saturnia, another thermal area, and I stayed there with AirB&B. Amazing experience, a little too far from Florence, but worth it!