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Two Amazing Days in Montepulciano

Story and Photos by Sara Moore Edited by Amber Ballard

Spend two amazing days in Montepulciano with WanderMoore! In 2018, I had the opportunity to visit this amazing Tuscan city on a family vacation and loved every minute of it. We spent several days exploring and finding fun things to do in Montepulciano, including local wine tasting! I planned our own, self-guided, Montepulciano wine tour and it was one of the highlights of my time spent in Italy. We drank tons of Montepulciano wine, including Vino Nobile! My family and I also enjoyed dining, wandering, and experiencing the history of the city. Check out how to spend two amazing days in Montepulciano below:

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Why visit Montepulciano?

Montepulciano is a great home base to see many parts of Tuscany including Florence, Siena, Arezzo, and of course lots of vineyards. Pienza and Cortona are small towns that are within 30 km of the city. The city itself has a rich history, museums, churches, tons of shopping, great little restaurants, and gives visitors that quintessential small-town Tuscan experience. There are also many wine tours visitors can experience that depart from Montepulciano.

About Montepulciano

Located in Southern Tuscany, Montepulciano is a charming hilltop town known for its fantastic wine, charming squares and piazzas, and panoramic views of the Val di China valley. The city is full of elegant Renaissance buildings, medieval churches, and more wine shops then you could possibly ever visit. Most of which sell the famous Montepulciano wine, Vino Nobile. In the main square of the city, Piazza Grande, you will find the beautiful main cathedral and Terrazza Del Palazzo Comunale, the town hall.

A Brief History

The original city was founded by the Etruscan King Porsenna around the 6th century B.C. Over the years, the town continued to be built up on top of itself creating layers of the city. Today, you can still visit the original parts of the city as the caves are now used to house Montepulciano wine. In the middle ages, the city was fought over by the city-states of Siena and Florence.

In 1232, Siena took control of the city, and Montepulciano flourished for the next three centuries. During this time, the city became a key point along trade routes with a strong middle class which increased its wealth and trade power. The city continued to switch hands over the next few centuries. Finally, in the 15th century, the city experienced a process of renewal and new urban planning. Piazza Grande and several other key areas of the city were constructed during this time.

Later, the city was ruled by the famous Medici family. During this period many religious buildings were constructed including the main Cathedral. In the 19th century, Montepulciano became an important agricultural market and center for processing food products.

In recent years, Montepulciano has gained some fame due to being a filming location for New Moon of the Twilight book/movie series.

Where to Stay:

There are lots of places to stay in Montepulciano – all of which are pretty great. The city is divided into two different main areas to stay- within the city walls or outside the city walls. Both are great options; it just depends on what you are looking for.

Inside the city walls, you will find cute little apartments or Airbnbs to rent. Most are on little side streets and offer balconies where you can take in the vibe of the city. Upgrade and find one with a view of the valley, you won’t be sorry! If you are looking for a bit more space, stay outside the city walls. I would highly suggest renting a beautiful Tuscan Villa. Check out some amazing villas in Montepulciano HERE!

There are hotels and apartments to choose from in the area and all are just lovely. Search for hotels in Montepulciano below:

Getting to Montepulciano:

The two closest airports to Montepulciano are Rome and Florence. From there, travelers can get to Montepulciano by train, bus, and car. The nearest major cities, Florence and Siena, both of which offer bus and train routes. The main train station near Montepulciano is the Chiusi train station. Buses connect to the train station every hour. Pro Tip – busses sometimes don’t run on Sundays, so make sure to check the schedule!

I will say that renting a car does give you more options to experience Montepulciano wine tasting. You will need to rent a car, or hire a car, to fully follow my 2-day itinerary. Side note – cars are not allowed inside the city walls without a permit, so make sure to wear your walking shoes. There is convenient parking at key locations around the city, from there you can take the little orange bus to the city center, or enjoy the walk. 🙂 Suggested parking is P8 (Via dei Filosofi, 53045) or P7 (Via dell’Oriolo, 53045)- both are close to the city center. You can then enter the city through one of the main gates, Porta al Prato or Porta delle Farine.

Day 1

On your first day on Montepulciano (after you get there, park the car and all that) start out by just wandering around the city. The city has a lively feel, with tons of little wine shops, fashionable stores, pretty churches, and curvy side – streets to explore. There are also tons of places to eat in Montepulciano including coffee shops, wine and cheese bars, little restaurants, and Gelato places.

Montepulciano is the capital city of Vino Nobile, so you will want to make sure to try some of this wine while in the city. There will be plenty of options, trust me! There is a wine shop or tasting room on every corner. Make sure to find one that has some history behind it, with ancient cellars built into underground tunnels normally carved into the rock – these are amazing! I would suggest De’ Ricci both for their amazing storeroom, guest service, and great wine.

Enjoy a nice break at Caffe Poliziano. Grab yourself an Italian coffee and pastry – there are tons of yummy options. Find a spot out on the back terrace. You will be treated to a view more delicious than the pastries. After the coffee and pastries pay a visit to the Church of Sant’Sgostino.

Keep climbing (Montepulciano is a hill town after all) to the top where Piazza Grande or the city center is located. The piazza is surrounded by beautiful 15th-century buildings including, the Duomo and the Terrazza Del Palazzo Comunale, the town hall. The church is lovely and visitors can walk in and tour – a small donation is custom.

If you have any energy left, climb the Palazzo Communale tower after! For a small fee, visitors can climb many flights of stairs to the top where you will find panoramic views on all sides. On a clear day, you can even see Siena and Mount Cimone in the distance. A word of caution – the climb is strenuous and the stairwell is really cramped. Those who are afraid of heights, claustrophobic, or have any medical conditions that could be aggravated by climbing should not participate.

Day 2

On day two in Montepulciano, I suggest creating your own wine tasting tour. Follow my full guide to make it a perfect Montepulciano wine experience! If you don’t feel like driving yourself, there are lots of great tour options in the area as well.

Vino Nobile

The main Montepulciano wine you will want to taste on your tour is Vino Nobile or Nobile di Montepulciano. The name means, “the perfect wine, of noble men” and/or “of all wines, is the king”. It has been declared one of the best wines in all of Tuscany! Made up of primarily Sangiovese grapes, it has a ruby red color. For my wine lovers- It is a full-bodied wine with an intense bouquet full of hints of amarena, blackberry, and forest fruits such as cherries. It also has a fresh crisp flavor and the tannins are pronounced. Another great wine to try on your tour is Chianti Classico – one of my personal favorites.

Driving around the Italian countryside may be one of the most amazing experiences you will ever have. Add in Montepulciano wine tasting and it just gets that much better. Just be careful – make sure you have a designated driver or hire someone to drive you around- the wine will catch up to you quickly. In order for you to have the best experience possible, I have broken up the vineyards/wineries into regional areas – closest to the city, Mid-range away, and farthest away. I also would not recommend you visit more than three or four in one day. Most have really cool tours you can take and some will take up to several hours. See the self-guided tour options below:

Montepulciano Wine Tour #1- Cantine Dei, Montemercuio and Salcheto

Cantine Dei

This amazing vineyard just can’t be missed! Their historic buildings mixed with their new modern travertine cellar makes visiting Cantine Dei a Montepulciano Wine must do. You can also book a villa on-site for the full wine experience. Their wine tour offers you a taste of 3 wines and takes about 45 minutes. To visit for yourself, get all the additional info you need on their website- HERE!

Montemercurio

A small vineyard, located close to the city, Montemercurio has been family owned for over 50 years. Their tasting room is open 10 a.m. to 6 p.m. each day- on the weekend you must make reservations before visiting. To book a tasting, visit their website HERE!

Salcheto

Salcheto, meaning Willow Tree, is located just outside of the city. You can take a tour of their cellars or order wine by the glass. Make sure to leave time to grab a bit at their restaurant, The Enoteca. Salcheto also have a 13th-century Villa you can book and stay right on-site. Visit their website for more info- HERE!

Montepulciano Wine Tour #2- Cantine Fanetti, Boscarelli and Icario

Cantine Fanetti

Cantine Fanetti has open tasting hours from 10 a.m. until 6 p.m.- open each day except on holidays. You can taste their wine, olive oil, and tour the estate. Check out more info about Cantine Fanetti on their website- HERE!

Boscarelli

This small family-owned winery produces about 100,000 of the good stuff each year. They offer a variety of tours ranging from 10 Euros per person all the way up to 50 Euros. All the tours offer something unique and interesting but most importantly lots of wine. All tours must be booked in advance. Find more info on visiting HERE!

Icario

This 20-hectare vineyard, is situated just a few minute’s drives from Montepulciano. They offer several different tours and tasting options including their Classic Tasting Experience, Premium Tasting Experience, and Wine Lounge Prestige Experience.I recommended you book in advance. They also have an amazing patio with killer views! More info on their website- HERE!

Montepulciano Wine Tour #3- Poliziano, Villa S Anna, Palazzo Vecchio and Avignonsei

Poliziano

In the same family for three generations, Poliziano vineyard is worth the drive out of the city for some Montepulciano wine! Their tour includes a visit to the cellar, vineyard, historic archives, and a tasting of several wines. Paliziano also has a wine club you can join. For more info visit their official website – HERE!

Villa S Anna

Villa S Anna is a women-owned vineyard and has been in the Fabroni family for more than 200 years. Their wine tour/tasting includes a nice tour of the property and a tasting of 4 of their wines. The tour lasts about 1.5 hours in total. Check out their official website for more info HERE!

Palazzo Vecchio

Set on a 12th-century estate, Palazzo Vecchio started producing Vino Nobile in 1990. They offer a variety of options to taste Montepulciano wine. I would suggest their Tour and Wine Tasting package. You get a tour of the beautiful vineyard and a taste of 6 of their wines. The tour does take about 2 hours and must be booked in advance. To book a wine tasting or lunch experience check out their website- HERE!

Avignonesi

Located furthest from Montepulciano (although the driver really is lovely), this amazing vineyard is the perfect spot to start or finish your wine tasting day. I would suggest booking their Cellar Door Experience! They offer wine tasting, lunch options, and a variety of fun Tuscan experiences. These you must book ahead. They include balloon rides, cooking classes, and even a falconry experience. Visit their website HERE!

By the time you are done with a day of Montepulciano wine tasting, you will be exhausted! For dinner, take it easy and choose someplace near where you are staying, order the largest bowl of pasta possible, and head to bed early. 🙂

Montepulciano is a city I could return to again and again- I just loved it and I hope you will too! I hope my guide was helpful and informative. Make sure to comment or ask any questions below!

Check out some of my other adventures in Italy- HERE!

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About the Author

Sara Moore

Travel Blogger at WanderMoore | Website | + posts

Hi my name is Sara and I am the creator of WanderMoore! 🙂 I started WanderMoore in early 2020 after leaving a full-time job in the Communications/Marketing field to stay home and raise my kiddos, Mila and Liam. I wanted something fun to work on in my free time and WanderMoore has become one of my biggest passions! Thank you for reading my post! I can't wait to share more of my travel adventures with you 🙂

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