Tuscansanity?

I've been to Tuscany 4x and always homebased at my husband's free family accommodation in Lucca, so not speaking from experience. I see what you mean though about moving each day. I don't think it's such a big deal if your moving day doesn't coincide with a big trip too -- if you pack efficiently, you're ready to go when you get up and have had your coffee. Then you're only and hour or two down the road. I would do this trip, but I'd have to be ready to be light on my feet.

We’ve done two trips to Tuscany and are also wine lovers. We spent a week outside of Cortona the first trip and 3 nights in Montalcino the next trip. Here are my suggestions to tweak your trip.

Spend two nights in either Volterra or San Gigmano. They are so close you can easily do a day trip or stop on way to next destination.

Then go to Montalcino. Add at least 1 night. Montalcino is meant for wine lovers. There are tasting rooms in town so no driving later in day. Definitely make reservation in advance to Biondi Santi (birthplace of Brunello wines)

Next stop Montalcino. Drop your night in Cortona. You can day trip from Montelpulciano to Cortona, Easy 30 minute drive. Montelpulciano has wine tasting in town and wineries and vineyards in surrounding area. We spent a week there and while there’s wine to drink in Cortona, not many vineyards or locally wineries nearby.

So add the dropped Cortona night to Siena or yet another night to Montalcino (our favorite as wine lovers)

Let me know if you have more questions

Just don't drink and drive. You would hate to have to spit out the wine you are sampling.

Sounds like the perfect trip. Can I come?

Thanks for your replies - aside from the snarky reply on spitting during a wine tasting., which there will be some of too on drives through the heart of Tuscany and Rick’s Brunello drive. But thanks.

The suggestions for edits and tweaks to the itinerary are now under consideration and construction. I’m trying to plan for a little Chianti region before waving goodbye to tour bus tourists in San Gimignano at my late-in-the-day arrival, and I’m hopeful for a quiet-ish night and morning before the bus crush. Then, off to Volterra.

The Etruscan sights in Volterra and Cortona have me captivated. I’m torn. I’d like to give proper time to the Volterra sites. There seem to be some time intensive and amazing sites there. Is that misunderstood? Rick rates the Corona Etruscan sites with one pyramid and I wish I would have caught that earlier. I’m also eyeing up Arezzo along with the Cortona overnight. I’ve read it’s a nice visit. That’s how a night in Cortona made its way into the itinerary.

I’m trying to navigate and incorporate segments of the Crete Sinesi drive between Cortona, Montalcino, Montepulciano, and Siena overnights. I know there will be some back tracking, which I hate, but then I think of photo opportunities in different light conditions and I find it tolerable.

I am staying one night in Siena, reluctantly, but I convinced myself there is little to do there for nightlife. Il Campo fun slips into the night and disappears, unnoticed. So long as I can watch the sun shift over and into sunset on Il Campo, enjoy a Pici meal at a recommended restaurant, and buy that Sienese nutty cake thing to bring home, I’ll be satisfied with one lonely but lovely night in Siena.

Find a place. Park yourself there. Rent a car. Day trips. Taste during the day but drink at dinner when you are on foot back to the hotel. Enjoy

Thanks for your post! We have the same interests-wine, driving some and experiencing CT and Tuscany. I am planning a trip for the first of May. We are flying into Rome, train to Florence (2nights), then to Cinque Terra for 3 nights-noticed you listed CT - any advice on town to stay-or where-thinking about reserving Airbnbs. Then to Florence-planning on renting car by train station, Volterra/San G (2nights) then Montalcino and/or Montepulciano (4 nights-one place or split) Another post said I could leave car in Orvieto and take train back to Rome. Any advice appreciated-Have fun!