Things to do in Montepulciano, Tuscany: The Best Sightseeing Tours

March 29, 2022 Agatha Simes

Montepulciano makes a great base for exploring the Tuscan hill towns. Just make sure to pack well-broken-in walking shoes, because cars aren’t allowed in the center of town. Explore the Duomo of Montepulciano and the Palazzo Tarugi… or sample the local wine, Vino Nobile di Montepulciano, which has been praised for centuries.
Restaurants in Montepulciano

1. Private tour Brunello di Montalcino and Nobile di Montepulciano wine experience in Tuscany

Piazza del Duomo, 50122 Firenze FI, Italy Tuscan Safari
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5.0 based on 4 reviews

In this p tour, you will travel from your hotel/accomodationton the historic town of Montepulciano, sampling its atmosphere and wine before moving on to the Tuscan hill town of Montalcino. Afterwards, you will be driven back to Florence via the panoramic Cassia Road that travels through the beautiful Tuscan countryside. From there you will be driven to Montepulciano where you will have time to enjoy wines in Contucci Here you will be able to take part in a wine tasting before traveling onwards to Montalcino, departing at around 12noon.Montepulciano to Montalcino. The first stop on this section of the trip will be a  wine farm, or similar, where you’ll enjoy the farm’s own wines. Montalcino. Then it is  to the medieval hill town of Montalcino.. You will be able to walk through its charming city centre and see its medieval fortress – guided by your tour leader.Return to your hotel/accomodation You will arrive back in Florence city centre at approximately 5pm.

Inclusions: Wine tasting, Driver/guide, Hotel pickup and drop-of

Exclusions: Gratuities

Reviewed By Lisa M

The day was good however a couple of constructive feedback points for you 1) when I first looked at the trip the meeting point was at the end of the road the hotel was on, however your e-ticket and website made us go to the main bus station 20 mins tram ride away and the tour guide commented as I hadn’t checked in a Julian’s Bar, as everyone else had. 2) the second point is to do with the final leg of the trip in Siena, when it was pouring with rain and we were about to head back to the bus and the tour guides boss had come up with another great idea for the small cost of €3 everyone could get the trenino back to the bus, half the clients didn’t want to do this and we were made to stand in the rain getting wet whilst the main tour guide waited for the trenino to arrive before the walkers were allowed to set off on foot back to the bus. Had I not stepped up and asked for the walkers to be allowed to walk with a guide without waiting, we would of been soaked!

2. Private Tour: MONTEPULCIANO Wine Tasting Experience

52044 Cortona, Province of Arezzo, Italy Do it in Tuscany - Tours & Services
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5.0 based on 2 reviews

Private guided wine tour and tasting in Montepulciano, Tuscany to discover Nobile and the most amazing wine estates and cellars in town and in the wonderful countryside,famous for its rolling and soft hills, vineyards and olive groves.

Inclusions: Lunch, Wine tasting, Snacks, Tour escort/host, Private tour, Alcoholic Beverages

Exclusions: Gratuities, Hotel pickup and drop-off outside of Siena and Arezzo province - to be quoted

Reviewed By smolly7

Having arrived in the Cortona area with very little planned I researched a few things to do. Finding this fabulous company was wonderful after emailing late (very late) on a Saturday evening Federica made everything happen seamlessly for a 10am pick up the following morning. We were met by a passionate bundle of energy called Francesco who proceeded to give us a fabulous walk through history and the process of growth and harvest on the way to our first stop. Francesco’s knowledge of the regions and the individual wines was extensive. He was and engaging and patient with our questions. Each vineyard was a contrast to the next, in regards to the process of winemaking. We were throughly relaxed and the day was full of laughter from start to finish. We truely can’t thank the team enough for giving us such a fabulous insight into the regions wines and countryside. If you’re ever in the area allow this business to look after you it is a must while in Tuscany. Ciao????

3. Montalcino and Montepulciano Tour from Florence

Piazzale di Porta Romana, 50125 Firenze FI, Italy Tuscany Private Tour
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5.0 based on 1 reviews

Travelling in Val d'Orcia is an unforgettable experience. Your eyes become dazzled by the beauty of the colours of this land, unsurprisingly a UNESCO World Heritage Site. This tour has been created for you to discover the most painted corner of Tuscany, made of enchanted landscapes, tree-lined avenues. Sunrises and sunsets of extraordinary, unique colours in the world are one great addition when wandering the road from Montepulciano to Montalcino through Pienza, considered one of the most amazing routes of Italy.

Inclusions: Departure from your hotel, Visit of Montepulciano, Typical tuscan lunch + wine tasting + visit of a winery, Visit of Pienza, Visit of Montalcino + 3 wine tastings, Languages: Italian, English, Lunch, Alcoholic Beverages

Exclusions: Gratuities

Reviewed By 628brendah

What an amazing day! It started with truffle hunting with Roberto and his two dogs - Ori and Chloe! We learned a lot about truffle hunting and how the dogs are trained. Chloe was 'in training' and it was fun to see how Roberto used both dogs. They found about 12 truffles in all of various sizes! Then we headed to a small family winery where we ate the fruits of our labor!!! We had a 4 course 'absolutely delicious' meal, tasted a lot of great wines, in addition to olive oil and honey! We even bought a bottle of wine to take with us and watched Sylvia add the DOCG label by hand (which are closely tracked by the region)! We had a great tour guide, Paelo, with us the entire day! He picked us us at our farmhouse, was our translator when needed, was very courteous and informative! I would highly recommend this very unique experience! And I would recommend Tuscany Private Tours. They were very easy to communicate with and very responsive!

4. Private The Essence of Tuscany: Chianti Classico, Montalcino, Montepulciano

Caf Tour & Travel
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5.0 based on 1 reviews

Following the scent of the Great Wines through the most stunning landscapes of Chianti, Val d’Orcia and Val di Chiana

Inclusions: Pick Up and Drop Off at the hotel in Florence if centrally located, Transport by deluxe ari-conditioned vehicle with WIFI on board, English/Italian speaking driver, Typical Tuscan Lunch in a family run Farm, Wine and Food Tasting with 3 wines and local products in a cozy Winery

Exclusions: Gratuities, Everything not mentioned as Included

Reviewed By aakebe

Only 7 people and the tour was by Van. The driver guided us during the drive but no guide joined us at our stop in Castellina. Professional presentations at the wineries. Especially at Poggio Amorreli with Andrea where we were treated with Spumante, one white and two red Chianti and one supertuscan. We also got bread, cheese, salami with their own balsamic vinegar and olive oil. The driver called for a taxi upon arrival in Florence ????

5. Orvieto and Montepulciano Wine Tasting Private Day Tour from Rome

Rome Italy Explora
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5.0 based on 1 reviews

Want to visit Italy, but looking to see more than just the tourist cities? Orvieto is your answer and is perfect for a day trip from Rome. The historic, and beautiful section of the city is located at the top of a steep hill. The well-preserved Gothic and medieval buildings will make you feel like you're frozen in time. You can easily walk out of beautiful architecture, historic buildings, or interesting spots to people-watch. Montepulciano, Montepulciano, Montepulciano, Montepulciano, Montepulciano, Montepulciano in Italy and abroad. Montepulciano has a distinct peculiarity, in which you have been dug out underneath the prestigious palazzos.

Inclusions: Pick-up and drop off with luxury transportation and private chauffeur, Private English-speaking tour escort at your disposal, Entrance tickets in the Orvieto Cathedral (Duomo), Light wine tasting in Orvieto, Visit to the most ancient and beautiful wine cellar in Montepulciano, Wine tasting with three different wines in Montepulciano, Snack with local products (cheese, cold cuts) in Montepulciano

Exclusions: Food or drink choices made outside the scope of the organized tasting tour, Gratuities (optional)

Reviewed By GiulianaD137

We wished we could see Pope Francis but we could never expected we could see him so closely thanks to Rossana great effort. Rossana and our driver Luigi are both great persons and the visit to the Pope very well organized. They both were professional, supportive, engaging and very helpful. Rossana took really a great effort to make the visit tailored to our needs and she had great sense of humour. Big thanks to R and L. We would highly recommend this tour.

6. Montepulciano from above!

Porta al Prato, Via Gracciano nel corso, 53045 Montepulciano SI, Italy Elisona Lishi
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5.0 based on 1 reviews

That's a walking tour in the center of Montepulciano. We are going to visit the main attractive, the narrow streets, the panoramic views of the town, then we will go up in the Tower Hall, the highest point of Montepulciano to have a breathtaking view of the Valleys around the city. Then we will finish the tour with a Wine tasting.

Inclusions: We are going to an ancient Wine Cellar so you can taste the Vino Nobile di Montepulciano.

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7. Civita di Bagnoregio + Orvieto + WineTaste in Montepulciano Private Tour from Rome

Rome Italy Explora
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5.0 based on 1 reviews

Want to visit Italy, but looking to see more than just the tourist cities? Orvieto is your answer and is perfect for a day trip from Rome. The well-preserved Gothic and medieval buildings will make you feel like you're frozen in time. Together with Montalcino, Montepulciano is well known for the great production of red wine, it "Noble of Montepulciano" is one of the most appreciated Italian wines in Italy and abroad. Civita di Bagnoregio is a magical, surreal, fantastic place located on a top of a hill that can only be reached by crossing a narrow pedestrian bridge. Nick-named "the town that is dying", two citadel has Etruscan and Medieval origins. Suspended in time and space, Civita di Bagnoregio is beyond doubt one of the most beautiful and characteristic Italian villages. Arm yourself with a camera because you will be faced with breath-taking views!

Inclusions: Pick-up and drop off with luxury transportation and private chauffeur, Private English-speaking tour escort at your disposal, Entrance tickets in the Orvieto Cathedral (Duomo), Light wine tasting in Orvieto, Visit to one of the most beautiful wine cellars in Montepulciano, Wine tasting with three different wines in Montepulciano, Snack with local products (cheese, cold cuts) in Montepulciano, Entrance tickets to Civita di Bagnoregio, Free time in Bagnoregio

Exclusions: Gratuities (optional), Food or drink choices made outside the scope of the organized tasting tour

Reviewed By GiulianaD137

We wished we could see Pope Francis but we could never expected we could see him so closely thanks to Rossana great effort. Rossana and our driver Luigi are both great persons and the visit to the Pope very well organized. They both were professional, supportive, engaging and very helpful. Rossana took really a great effort to make the visit tailored to our needs and she had great sense of humour. Big thanks to R and L. We would highly recommend this tour.

8. Val d'Orcia private tour: Montalcino, Pienza and Montepulciano

Ciao Florence Tours and Travels
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5.0 based on 3 reviews

Experience the heart of Tuscany by visiting the enchanting Val D’Orcia led by your private driver. Let your personal chauffeur do all the work and take you on a journey through the spellbinding Val D'Orcia countryside, a region known for its scenic beauty, picturesque villages, rolling hills and cypresses! Explore in total freedom the enchanting towns of Montalcino, Pienza and Montepulciano and savour the best wines in the world! The first stop will be Montalcino, land of the world-renowned Brunello wine, a labyrinth of cobbled streets, quaint wine shops and Romanesque-style churches. The following stop is Pienza, which stands high upon a hill and dominates all the Orcia valley with extraordinary views. The last stop reaches Montepulciano, home to the famous Vino Nobile vineyards and more recently famous for the filming of the vampire movie "New Moon". Enjoy your free time in the most elegant village of the entire Val D'Orcia.

Inclusions: 9 hours chauffeur driven hire, Pick up & drop off at your hotel, Bottled water, Free time in Montalcino, Pienza and Montepulciano, Wi-Fi

Exclusions: Guided tours in the villages - Free time only

Reviewed By J Adam K

Took the walking tour today with Safe as our guide. Wonderful experience. Safe spoke flawless English and his passion for Florence, art and history was addicting. We hope to do something similar in the future.

9. Horseback riding with Tuscan picnic

Valdichiana Living, Piazza Grande, 7, 53045 Montepulciano SI, Italy Valdichiana Living
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5.0 based on 1 reviews

A horseback riding to slowly explore, in the open air, the most beautiful and scenic places in the area: a guided horseback riding through the Tuscan hills

Inclusions: Horseback riding (2 hours), Picnic based on typical products, Glass and glass carrier

Exclusions: Transportation service

Reviewed By mauds494

When we arrived at the agency, we were told that our booking date was 2 days later, I made a silly mistake when I booked it online. We were disappointed as we were really excited to have the guided tour. The lady at the agency directly welcomed us with a smile and a found a solution for our tour to happen the very same day , 1h30 later with just the 2 of us. Our first impression was therefore very good and the guided tour confirmed our idea. Our guide, Elisona was very kind and took the time to explain the history of Montepulciano to us. We were impressed by the cellars and had a really good time. The second visit was the best (Crociani) for the kindness , the good bread, olive oil and cheese and of course , the good wine. Elisona even helped us to bring the wine to our car that was down the city. We recommend! Thank you for the kindness ! Maud and Jacques.

10. Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting

Tuscany Top Drivers
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4.9 based on 7 reviews

Spend a day exploring the wine region of the Val d'Orcia (Orcia Valley) with this full-day private tour from Florence. With your private group of no more than 7 passengers in the vehicle, you'll visit Montalcino, Montepulciano, and take in the scenery of the Orcia Valley. Enjoy a Brunello di Montalcino wine tasting with lunch in a small family run winery. (Price is per group.)

Inclusions: Hotel pickup and drop-off, Private tour, Transport by air-conditioned minivan

Exclusions: Food and drinks, Lunch, Wine tasting

Reviewed By chiahkk

Teresa, our private guide was friendly and knowledgeable. She drove our family of 5 from Singapore in a big comfortable Mercedes van. She was a safe and careful driver. Teresa was professional throughout and gave us background information and history of places we visited or passed on the way. She helped us to book a restaurant we wanted for lunch at Siena. We ended the day a little later but she was cheerful to the end. I would recommend her tour.

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