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5 nights in Montepulciano - What to do?

Hey all,

We will be traveling to Italy on our Honeymoon from 9/20 - 10/8. All of the flights and sleeping accommodations have been booked. Here is our high- level itin:

Fly into Milan-train immediately to Venice
3 Nights in Venice - train to Florence
3 nights in Florence - bus to Siena
2 night in Siena - Rent car and drive to Montepulciano
5 nights in Montepulciano - On 5th day, drive to Pisa, drive to La Spezia and return car, train to Vernazza
3 Night in Vernazza - train to Milan
1 night in Milan
Fly home from Milan.

We have a pretty good idea what we want to do/see in every location but the 5 nights we are in Montepulciano. We will likely spend one full day exploring Montepulciano itself, but that leaves 4ish other days to explore the Tuscan hill towns. I was hoping to get some advice on how to spend those days. We are thinking about taking a day trip to either Orvieto or Assisi, but aren’t sure which one is more worth the time. We definitely want to spend at least 1 day with a hired driver and go wine tasting (any recommendations on a driver/tour company?). I would love to get some feedback on how other people would spend a few days with a car in Montepulciano. We don’t want to drive more than a few hours in a given day, so going to Volterra or San Gimignano will probably be saved for another trip (when we are in Siena, we won’t have a car and we just want to explore the city itself without travel). What other nearby places do you recommend visiting? We also would love to taste some Brunello in/near Montalcino.

About us: we are in our early 30's. We will be on our honeymoon, so we would like a somewhat slower pace, but still do things. We love wine and good food. We are active, like to run, go on hikes etc. Also, we generally like going to museums and seeing art, but don’t want to spend entire days indoors. Generally, we are up for anything.

Thanks, and we appreciate your advice in advance.

Posted by
1757 posts

First, it's only about 2 hours' drive from Montepulciano to either Volterra or San Gimignano. You could easily visit both in a day, and it won't feel like a lot of driving. In fact, the whole region is very scenic, so you will enjoy the views. If 4-5 hours driving time is too much for you in a day, saving this for another trip is a fine option.

There are dozens of towns you can drive to from Montepulciano. You can figure out itineraries with a map so you can combine multiple destinations in the same direction on the same day.

I haven't been to every town in the area, but for the day you visit Montalcino, I'd recommend also visiting Pienza, Castelnuovo dell'Abbate and the Abbazia di Sant'Antimo, Bagno Vignoni, and Castelnuovo d'Orcia. That can be done in an easy loop. I'm not sure what itineraries to suggest for the other days, but there are probably more experienced Tuscany travelers on this forum than there are people living in Tuscany! You should end up with lots of good advice!

Have a great trip!

Posted by
297 posts

We spent 4 nights in Montepulciano in 2013. We did one day trip to Pienza then on to Montalcino. Another day trip to Cortona. And one day exploring Montepulciano.

We are planning another trip for Sept 2017 and staying there and doing day trips to Assisi, revisit Montalcino, and let the day lead us. The drive is so scenic. We only wanted to travel no more than 1 1/2 hours each way either, and it gave us the time to just stop anywhere we saw something interesting.

Congrats and enjoy your honeymoon. What a wonderful place to start your journey.

Posted by
7337 posts

Because of your honeymoon comments I suggest that you consider booking (internet or through your hotel) a tasting lunch at a winery that has an ambitious restaurant. We let our hotel choose, but we were pleased with Poggio Antico and even happier with Aviognesi. Note that this is not the same as the current vogue for artisanal Agriturismos that (?) still use their feet to press the grapes! (Just kidding.) We were let down by the very famous Antinori experience.

I hope Siena is less crowded in September. Driving in Tuscany is not "hard", but it is time consuming. Learn what is a ZTL. Be sure to see a tiny town or two. Google Images can be helpful for late research.

Posted by
683 posts

I have not been to this area, but have been reading about it in preparation for next summer's trip. One drive people commonly recommend (and which looks great to me) is from Montepulciano to Montalcino. There are a number of side trips you can take off that main route.

For walks in the area, you might look at Walking and Eating in Tuscany and Umbria by Lasdun and Davis. Besides detailed walking information (including one walk from Montepulciano to Pienza), there is a lot of information about restaurants and wineries.

Congratulations, and have a great trip :-)

Posted by
4105 posts

Great guide for wonderful wine and food.
http://www.winewordswisdom.com/travel_itineraries/southern-tuscany-wine-tour.html
So much of this can be done in Montepulciano, with 2 day side trips.
Try to take a wine tour while in Siena or Florence. The Chianti wines will give you a good contrast to the Brunello and the drive is beautiful.

We buy an assortment to take back to our lodging and drink there. Not risking drinking and driving. The rest comes home with us.

Congrats and have a great time.

Edit: this is a fantastic place for a tour and either lunch or dinner. Well worth the price.
http://www.vignamaggio.com/en/attivita/degustazioni-visite-guidate/