Montepulciano: The Tuscany Vacation You’ve Been Dreaming Of

Overall vibe of Montepulciano:

Montepulciano is one of my favorite places I’ve ever been. It’s nestled right in the beautiful Tuscan hills and has an incredibly charming, historic, peaceful vibe. It’s a quaint town with some incredible restaurants, cute shops and tons nearby activities like hot springs, wineries, day trips to other cool towns, etc. The views from Montepulciano, because you’re on top of a hill, are amazing (say hello to the best sunsets ever).

OH, and the place we stayed in Montepulciano was an actual DREAM; I can’t wait for you to see it below!!

Quick Guide to Montepulciano:

Overall vibe: charming, historic town with quintessential Tuscany vibes all around

How long to stay: 4-7 nights (we stayed 4 but felt like we never wanted to leave!)

Where to stay: Precise Tale Poggio Alla Sala was our fav place we’ve ever stayed!! Otherwise, I’d stay ideally within 15-20 min of Montepulciano.

Getting around: rent a car

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Where to stay in Montepulciano

We stayed at Precise Tale Poggio Alla Sala and I can hardly find the words to tell you how truly DIVINE it was. If you have a chance to stay here, do it! The property is huge and surrounded by stunning vineyards and rolling hills. The architecture and interior design is absolutely STUNNING. The restaurant is lovely (the included breakfast was so good and we enjoed dinner here a few times too). The staff is lovely (they made restaurant and activity reservations for us which was SO helpful as we don’t speak Italian). The outdoor pool is magical underneath the Tuscan sunshine. It’s a 15 min drive from Montepulciano.

We stayed 4 nights which was really great (any shorter would have really felt like we were cutting it short) but we could have easily stayed a week. It’s the perfect spot to both relax and explore as much as you want (Montepulciano, wineries, hot springs, cooking classes, horseback riding and so much more)!

Best restaurants in Montepulciano

Osteria del Conte: Montepulciano restaurant. White wine super good. Very peaceful cute restaurant. Great service. Truffle pasta and duck pici soooooo good. 

Osteria del Borgo (Instagram: @osteriadelborgomontepulciano): cheese and meat plate AMAZING. Stunning patio with views of Tuscany countryside. Great for sunset dinner. Make reservation. Gnocchi just okay (I don’t think we love gnocchi) and pici carbonara AMAZING (one of my favs we had all trip) and Florentina steak with rocket really really good. 

charcuterie board at italian restaurant in montepulciano

Osteria del Borgo

La Schiaccia Dell'opio (Instagram: @laschiacciadellopio_): soooo good. I got make your own prosciutto tomato arugula pesto buff mozzarella. The walnut cream one was also amazing.

italian panini

La Schiaccia Dell'opio

Here are 3 additional restaurants (recommended by our hotel) we would have tried if we stayed longer:

Best things to do in Montepulciano

Eat Pici Pasta: Pici is a thick, hand rolled pasta typically made from flour and water (think spaghetti or bucatini but much thicker) that originated in Tuscany. It’s SOOOOO good. We tried tomato sauce pici, pici carbonara, duck pici, pesto pici and loved it every single time.

Pici Pasta at Trattori di Fiorella, Pienza

Sunset in Montepulciano: This is a must; the sunsets in Montepulciano are some of the best I’ve ever seen. The bar, Romantico, is the perfect spot to watch. There’s a lookout that you can watch from right by the bar (whether or not you actually go to the bar).

Sunset At Romantico Bar

Go to a hot spring: There’s tons of natural hot springs in Tuscany you can explore. We went to Terme San Filipino and it was one of our favorite experiences in Tuscany. There was a good amount of people there but it wasn’t overwhelming crowded (we went on a Thursday around 10am). Make sure you wear a bathing suit and ideally, shoes you can swim and walk across rocks in, like Tevas (these are the ones I have).

Take a cooking class: We were going to do one at Fattoria San Martino but my intuition ended up guiding me to cancel and rest by the pool instead. Our hotel recommended that one as well as Argiturismo Sanguineto and Argiturisomo Coganello.

Have a pool day: The pool life in Tuscany is underrated!!! It’s so sunny, the views are magical and the energy of being outside in Tuscany is just so grounding and peaceful.

Go to a winery: See below.

Take a day trip to other nearby towns: See below.

Best Wineries Near Montepulciano

Day Trips From Montepulciano

Pienza: Pienza is a very charming small town on a Tuscan hill with beautiful views. It’s a great place to walk around for a few hours and grab a traditional Tuscan Lunch.

We had lunch at Trattori da Fiorella, an adorable Italian restaurant with delicious, authentic Tuscan dishes.

Siena: Siena is another cute town in Tuscany to explore for a few hours. There’s very rich history here so it’s really cool to see but since it was super crowded, I preferred Pienza and Montepulciano.

Montalcino: Another cute hilltop town recommended by our hotel. We didn’t go to this one but if you have extra time and want to explore more, it looks like another gem.

Google Map of All Montepulciano Recommendations

I saved all of my recommendations for you in the map below to make it super easy to get around! Here’s the full link so you can save it: https://www.google.com/maps/d/u/3/edit?mid=1LscF0iLGPggwzInH33REvmnLfy-RWBE&usp=sharing.

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