Driving from Bologna, only for two days


New member

We've been delighted to read this forum for days.

We will be traveling Italy during our honeymoon this May, and unfortunately will only have a weekend (Friday night until Monday morning) to travel Tuscany.

First timers, absolutely fallen in love with Montalcino and surroundings.

Now we need some advice from experienced fellow.

What would be our best itinerary? We will be starting on Friday night from Bologna (we can rent a car, take train, whatever works the best).

What we are looking for:

1- Drive around some of the most gorgeous sights. What you recommend? Chianti, Montalcino look wonderful. Consider we would only have saturday and sunday for this

2- Two or three MUST visit wineries in the region, hopefully those with nearby amazing Osterias, sights, open fields, and obviously great wine.

3- Any great cheeses around?

4- Lastly, and importantly, where to sleep? We found Castello di Velona in tripadvisor, and looks amazing. We would rather stay somewhere easily accesible for us to continue our journey around the region on Sunday.

Thank you all for the recommendations, we are just overwhelmed with places and regions in tuscany and would like to make the most out of the weekend (hopefully enjoying a couple of the best places, instead of running around and overlooking what truly matters).

P.S: Forgot to say we want to make sure not to miss this sort of sights - Crete Senese? - (http://www.panoramio.com/photo/346269) since we're both avid photographers. And looking to drive ourselves around into a relax and charming weekend, rather than a fully guided tour.


New member
Anybody? Please help us. We have most things figured out, however a helping knowledgeable hand will be highly appreciated.


The Tuscan Expert ;-)
Staff member
Ciao jakem, sorry for the delay! lots of questions lately and I'm behind on answering all of you, unfortunately.

First, congrats on the upcoming honeymoon trip! Wish you had more time for Tuscany but it also a great excuse to make it back again - maybe for an anniversary ;-)

Yes, Montalcino but Val d'Orcia in general is the perfect spot that meets all of your criteria!!

Since you're avid photographers and want great cheeses, I highly suggest the Val d'Orcia and Crete Senesi which are what postcards from Tuscany look like. That link you posted is from around San Quirico d'Orcia - you'll love the area right around there!!
As for where to stay, take a look at the places I recommend in San Quirico and Pienza on this post.
We've stayed in San Quirico twice, we love it! We really liked Casa Lemmi - comfortable, charming, nice breakfasts.

You'll need the car - only way for you to get around the area easily. Also plan on walking - the places you see like in that picture can be reached by taking the "white" or unpaved roads between the farmhouses that cover the entire area.

Pienza is famous for its pecorino cheese - visit and you'll smell it in the air. You'll find many shops in town offering tastings and chance to buy lots ;-). It is another reason why we also love the area lol!

And as for wineries - you can head to Montalcino or to Montepulciano, both important wine regions. Obviously both have lots of wine shops in town where you can do tastings, many run by local wineries. Most wineries aren't just open to the visits but many that do are open on the weekends. So search for and contact these ahead of time and see whether you need to arrange something ahead of time or not:
Montalcino - Casanova de Neri
Montepulciano - Avignonesi, Contucci (has wine shop in center of Montepulciano), Dei or Ricci
or go to the Consortium shop where you can taste all of the members wines (pretty cheaply! note it is closed on Sunday)

Many of the wineries ALSO offer accommodation - so a great choice would also be to stay at one of them - you'll have great views and wine right where you are!

Lastly, take time for good meals - and ask for "house wine" since being in the area guarantees having local wine! ;-)