Montepulciano is a common “day trip” in Tuscany. Tuscan towns are often popular for day trips as they are “smaller” and you can navigate them within a few hours and feel like you’ve seen it all. The key term being “feel like”. There is no way you can see it all, and truly experience these places in a few hours. You certainly can’t do it in 24 hours either, but an overnight is at least a bit more personal. You can experience sunrise and sunset, dinner in a local spot, and staying in town.
We spent 24 hours in Montepulciano and honestly I wish we’d spent more time. I know we’ll be back one day (and I’ll update this post). But until then, here is my best advice for how to spend 24 hours in Montepulciano, Italy.
12:00 PM
Start by checking into Residenza Fabroni. I can not express enough how wonderful the experience of staying here really is. This is a historical home dating back to the early 20th century and still contains so much of that original charm. They have 3 suites and they are all so stunning. We stayed in the blue suite as we were traveling with friends and it had two bedrooms. One bedroom faced the town and had the most lovely street view, the other faced the rolling hills of Tuscany. Even the bathroom had the most incredible view of the surrounding landscape and I could have sat there for hours staring out the windows. The family who runs this place were so kind and welcoming and we loved having such a local experience with them. The best part of this hotel was the rooftop and it will be mentioned later in the day!
1:00 PM
Another aspect of staying at this hotel that I loved was all of the local connections that the family had in town. They gave us a recommendation to go to “Enoteca La Dolce Vita” and told us to mention that we were staying at the Residence. We took their recommendation seriously and went straight there after checking in.
We ordered a charcuterie board and some pasta to try straight away! We mentioned that we were staying at the Residence and they brought out a bottle of “Chandon Garden Spritz”. They gave us each a good pour on the house while giving us some more recommendations for exploring the area. Turns out we REALLY enjoyed that drink and ended up buying more to have over the weekend. We tried some red wine here as well since we were in Montepulciano after all. The food here was wonderful, the vibe was fantastic, the staff were so kind, and all in all it was a great way to start the day in this wonderful town.
3:00 PM
Now you are full and ready to hit the streets! We spent basically the entire afternoon walking the streets of the town, popping into shops and Enotecas and just enjoying all that Montepulciano had to offer. There are so many possible stops you could make that I could never list them all, but you really can’t go wrong either.
You wouldn’t know it from the outside but some of the shops in this town actually have cellars where you can go down underground inside the shop and explore cellars with barrels full of wine. They allow you to taste as well sometimes for a small fee or for purchase of some bottles.
This is the period of the day where you may also want a quick coffee or cafe break because you have a big evening coming up back at the B&B!
5:00 PM
Head back to the Residence for the most epic part of this 24 hours. One of the most special aspects of staying here is that they offer a “Rooftop Wine & Local Product Tasting”.
They served us so much food and wine I can’t even remember it all, and all of it was amazing! They started with a charcuterie plate with all different types of meats and a sparkling white wine. Then we tried various types of bruschetta with local products and a beautiful white wine. This was followed by a local cheese plate and a move into some of the red wines this region is known for. I stopped taking photos at this point but we also tried some beautiful stuffed peppers, smaller panini, and more red wines from the region.
We watched the sunset on the rooftop while finishing our tasting, listening to music, and learning more about the area. This experience is one of my favorite that I’ve had in our travels and absolutely a top experience in Italy. I couldn’t recommend staying here more highly.
8:00 PM
We were literally so full and happy from our rooftop tasting but we didn’t want the night to end so we found a random Osteria that was open and got some more pasta to share. We wandered the streets a little more before heading home to sleep. This town got really quiet at night, which was really nice. I believe many people day trip here so mornings and evenings were much quieter. It should also be noted that we were here on a Thursday (not a weekend).
9:30 PM
Back to the hotel to relax and get ready for bed. There isn’t much nightlife to note in this town so you’re not missing out on anything. I also wanted to get up early to explore more. If you’re more of a night owl you could likely still find a spot to sit up and visit or have a few drinks.
8:00 AM
Get up early and wander the streets before the town fills up. It was so calm and quiet, the perfect time to walk all around, take pictures, take in the views, and just enjoy the peacefulness of it all.
9:00 AM
Another amazing perk of where we stayed was that they give you a voucher to go have breakfast at the most popular and delightful cafe in town, “Caffe Poliziano”. This place is one of the most popular for a reason, you can tell as soon as you enter. It is feels like a walk back in time, it is absolutely beautiful and so lively! The best part, which you’d have to go inside to know, is the incredible views this cafe has! Seemingly endless views over the rolling hills of Tuscany. The food here was delicious too and I had possibly the best chocolate filled croissant of my life here. You could also get “American” breakfast here too if that is more of what you’re looking for. They also have a stunning event space! In another life I would get married here! Maybe another vow renewal spot for the future!
10:00 AM
After breakfast we made a visit to the city hall to climb to the top and get some beautiful views over Montepulciano. Any town you’re in in Tuscany, if you can get to the top of a tower, you will be rewarded with truly epic views. It is always worth it! We explored the streets a bit longer before heading out to Siena for our friends wedding.
If I had another 24 hours in Montepulciano
If I had another 24 hours I would 100% spend it visiting some wineries around the area but outside of the town. There is nothing I love more than wine tasting on a Vineyard and I’d love to explore some of the vineyards in the area.
Want more to do in Tuscany?
I also have a long weekend in Tuscany itinerary written up, this included a wedding so I added some things we would have done, had there not been a wedding. I also listed Lucca as one of the places I’d love to go and I will be visiting Lucca soon so I will report back!
If you’re interested in that blog post you can find it here —> 4 days in Tuscany
Where to stay in Italy
If you’re interested in other parts of Italy I have visited and where to stay I also have a FREE guide to all of my favorite stays. You can find that here —-> FREE Italy Stays Guide
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