4.5 Days in Tuscany
 

Hi All!

My husband and I will be in Tuscany from September 27th-Oct 2nd (5 nights and 4.5 days) and will be staying in Montepulciano @ Salcheto Winehouse and will be coming from Montefalco in Umbria. Our main priorities are food, wine and views. I don't need to plan out every detail of the day but I'd like to have an idea of what we want do in general every day., especially because we want to visit wineries. We will have our car (don't worry, I know not to drink a lot and drive :) ).

Can you please help me decide how to piece the days together? My husband wants to fully plan a day on his own as a surprise so I have 3.5 to decide on. I want to visit Cortona (I am thinking on the way to Montepulciano), Chianti, Montalcino/Pienza/Montepulciano, Chiusi, San Antimo Montasary.

My questions:
1. How to best piece this together?
2. Should we visit Cortona on the way to Montepulciano or do it another day? Which other towns could we pair with this?
3. How would you do a day in Chianti?
4. Do i need to make reservations at all the wineries or do a lot of them just do walk in? I'd really prefer not having to stick to a schedule.
5. What else do you suggest we do?
6. Any recommendations for vineyards/agriturisimo to have lunch with a view?

Thanks in advance!

I'm not a big fan of Cortona, but I like the route going past Trasimeno. I'd rather take the ferry and walk around Isola Maggiore.

Chianti would be a little far for me if coming from Montepulciano. But if you're fast sightseers and got an early start, you could probably visit Castellina, Panzano and Radda. Try to fashion a driving route that circles more than backtracks.

I thought Abbazia di Monte Oliveto Maggiore near Asciano was much more interesting than Sant'Antimo, but it does close for a few hours in the middle of the day so you need to plan your visit.

AFAIK, most wineries don't accommodate visitors without reservations. You could search those that accept walk-ins and just keep that list with you as you drive around.

Other than the day in Chianti, what other towns do you plan to visit from Montepulciano?

Not sure how you are planning to group your days. I think Pienza/Montalcino with Sant'Antimo makes sense, but I would not combine it with Montepulciano.

In Montepulciano, there are several cantine (wine cellars) that offer tours and tastings. You do not necessarily have to reserve.

When we were in Montepulciano, we were interested in a winery tour with wine and olive oil tasting. We were able to book it through an office in the town that promotes the local wines:

http://www.stradavinonobile.it/en/homeen/

On the website, you will find some other suggestions for activities.

Jean- We plan to visit Cortona, Montalcino, Pienza, Chiusi. I was hoping for some more suggestions :) I just finished planning Piedmont, Umbria and Bologna and now I am starting to get lazy with Tuscany. I just want to get there already...

Thanks for the tips ladies. More welcome of course :)

I may be projecting a bit, but after your time in Umbria, you may start feeling a bit of hill town fatigue. Or at least I felt that way at some point during our last two vacations in Umbria. I loved all the towns, but at some point I just needed a break. If you suspect you might feel the same, schedule some time for a hike, horseback riding, a cooking class, etc.