Tuscany with no reservations

June is a very busy season, and I personally would not feel comfortable going around without reservations. Hotels will be booked up and you run a risk of not finding a room. I wouldn't feel comfortable just as 2 people, but especially as six I think you would find it very difficult to find a hotel where you can all stay together.

Ditto to Devon's response. You may have enough difficulty as 2 persons....with 6 that's a tall order for any hotel almost any time of year on no notice. At a minimum, you might travel with a list of 3 or 4 of your top choices for any place you anticipate spending the night, then start contacting them the day you decide to stop there and see if any have openings. At least you won't be going in blind. But I personally don't enjoy spending part of each hard-earned vacation day looking for a place to stay. After all, vacation time is money, too. The more time you spend looking for rooms, then going through the whole check-in/check-out scenario, the less time you will be seeing Tuscany. And consider that almost any place in Tuscany is reasonable driving distance to anyplace else in Tuscany. "Reasonable" in my opinion is less than 2 hours. You could easily pick a town in central Tuscany fairly near Siena and use it as a base the entire time. Some days you'll drive 15-30 minutes, some days you'll drive 1-2 hours. This way you unpack once, don't have to worry about luggage being stolen from your car while it is parked and you are off sightseeing "en route" to your next unknown destination, and get the convenience of sleeping in the same bed every night.

Good for you for asking far enough in advance to be able to profit from the advice you're getting! It's a really bad idea, for the reasons listed above. Consider an agriturismo as your base, and drive from there. Happy travels.

Not a good idea. We just got back from a two week Tuscan vacation and I can tell you I would not want to spend any time thinking about where I would be spending the night. Driving is not easy and it's best to have a home base where you can than venture out and explore. You will than get use to where you are and not feel so stressed every time you go out to a new town. We rented a farm house 8 miles north of Siena.

Terrible idea. Finding lodging in June for 2 is going to be difficult enough. 6? Almost nil. I'd park in an agriturismo (I stayed in one this spring near Montepulciano) and day trip to whatever towns strike your fancy, on your own schedule. That should give some "reliable" flexibility.