Should we see more places or fewer for longer?


New member
My husband & I (we are 50) are staying for 3 nights in Montepulciano in August. Day 1 we head to Siena from Florence & pick up our hire car at 3pm. We are looking forward to almost a full day in Siena. We plan to head to Montepulciano for our 1st night, stopping at Buonconvento & at the Abbey of Monte Oliveto. Is this enough for one day? Or should we also be visiting Qu'rico d'Oirca/ Asciano?
Day 2 we plan to visit Assisi & Spello. We think this is enough but should we also visit Citta della Pieve?
Day 3 will be spent visiting Montalcino, Abbey of Sant 'Antimo, & Pienza. Our 4th & final day will be spent exploring Montepulciano itself before heading to Perugia to drop off the hire car by 2pm.

How does this itinerary sound? We know nothing of Italy having never been there. This itinerary has come about from my own research. I'd hate to miss anything really worth seeing but don't want to waste time visiting lots of places but seeing nothing. We would like to spend time enjoying the moment; not rushing off & jumping in the car to get to somewhere else equally beautiful when we could stay put & enjoy.

Thanks for your input....


The Tuscan Expert ;-)
Staff member
less is definitely more ;-)

Ciao Pingelly,

3 days are going to fly by fast! I think you've already sensed you're trying to do too much in 3 days. You're in for a treat, Italy is so condensed with history, architecture, art... you'll understand once you're here. Soaking in the atmosphere is part of its magic, so slow down and enjoy being here rather than trying to "see" all that there is to see... in over 15 years in Italy, I am still discovering new areas in Tuscany! There is no way to see everything on one trip, but you can definitely experience a part of Italy and, who knows, maybe you'll come back for more!

Day 1 - just plan to spend the entire day in Siena - there are lots of things to see, head there early in the morning so that you do have time to see it and then head to Montepulciano. Depending on the time, you could stop at either Buonconvento or the Abbey for a quick visit - the abbey closes at 6pm, while Buonconvento is a small walled village that you can actually stroll around in and maybe have dinner there.
But maybe just head to Montepulciano to explore it already? eat dinner there, stroll around the town so you actually get to see it before you leave.

Day 2 - Try to visit Montalcino, Sant'Antimo, Pienza and San Quirico. This area is gorgeous - you will want to stop along the way to take pictures of the landscape and just soak in the atmosphere.

Day 3 - Explore Montepulciano if you haven't already, then head to Perugia. You might want to head to Perugia earlier than you think so that you can enjoy the drive there, so that is why you should see Montepulciano on your first day. Definitely enjoy Perugia.

Assisi and Spello are in Umbria, a drive past Perugia itself.... so it makes no sense to include them in your Tuscany itinerary. Maybe if you have an extra day after you head toward Perugia where you keep the car an extra day you could fit it in after, on day 4.

While distances don't seem far, the roads between Siena and the Montepulciano are all 2 lane country roads with beautiful scenery, you will want to stop and take pictures and enjoy the view. So better to try to see less and to take your time, than to try to fit too much in and not see anything, as you've already sensed it might be like.

Also consider August will be warm and very touristy, you'll find lots of people around! What days are you in Montepulciano? If they fall around the last Sunday of August, you won't want to miss the Bravio delle Botti - see pics here:
and details here: