What to do and see in Montepulciano, Tuscany: The Best Tours

April 22, 2022 Chanda Heide

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. 120 Minute Private Vacation Photography Session with Photographer in Tuscany

Tuscany, Italy Flytographer
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5.0 based on 1 reviews

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Tuscany and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in Tuscany, including where to eat & what to see from your vacation photographer. Return from your trip with beautiful, high-quality vacation photos — the best souvenir ever. We specialize in: - honeymoons - family trips - engagements - anniversaries - romantic getaways - multi-generational trips - babymoons - solo travellers - and just because! With over 10,000 5-star reviews, Flytographer is the global leader in vacation photography and has captured over 3 million memories for travellers across six continents. We’ve been featured across A-list media, including Conde Nast Traveler, Oprah, Forbes, Travel + Leisure, New York Times, BRIDES, Martha Stewart Weddings, InStyle Magazine, Elle, Buzzfeed, Refinery29, Huffington Post, & many more.

Inclusions: Private photo shoot with a professional photographer for individuals, couples and groups, Online image gallery delivered within 5 days of your shoot, 60 high resolution digital photographs, All taxes, fees and handling charges

Exclusions: Proposal photography not included with this package, Entrance fees to shooting locations, Food and drinks, Transportation to and from photoshoot

Reviewed By gratefulfortravel

We use flytographer all over the world when we travel, but it was fun to do a shoot here in Victoria during COVID. I would highly suggest if you're looking for good photos of your family.

3. 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 ????

4. Dining experience at a local's home in Montepulciano with show cooking

Montepulciano, Montepulciano, Tuscany Cesarine
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5.0 based on 1 reviews

Immerse yourself in a private dining experience at a local's home, enjoy an exclusive show cooking and taste authentic recipes from Montepulciano treasured in family cookbooks passed down by real Italian Mammas. Feel the warmth of Italian hospitality as you connect with local people. Enjoy a 4-course menu including starter, pasta, main course with side dish, dessert with drinks included (water, selection of red and white wines from regional cellars and coffee). This experience is held by Cesarine: Italy’s oldest network of 1000+ home cooks all over the country in more than 500 cities. They are passionate and welcoming hosts that open the doors of their own homes to curious travellers for immersive culinary experiences.

Inclusions: Private show cooking, Private 4-course dinner or 4-course lunch, Beverages (water, wines and coffee)

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Reviewed By touch_of_grey_SF

Having done several professional cooking classes in different countries, we re not new to this experience. This hosts for these dinners should do the same to better understand the expectations of their clientele. First the dinner we selected, as the title implies, was supposedly in Montepulciano where we were staying, and we were looking forward to walking to a local house for dinner. The dinner instead was 15 minutes by car in a neighboring town (montepulciano stassi I think) so that was not what we expected. Our host Barbara was very nice and we experienced a real cooking experience in her home which was tastefully decorated. However the menu consisted only of a soup appetizer and simple pasta entree and no second course - not a typical or complete Italian meal based on our experience. And the dishes were all very simple - pasta and tomato sauce and a soup which also had bread in it - no protein - and a basic wine. Given that the cost was in excess of $300 for a couple, this menu choice and wine - Rosso, the most basic tier of red wine - felt cheap to be honest. Given the cost and other experiences we had (in admittedly more expensive cities like London and Paris) the food and wine choices left us feeling little disappointed. Do this with the understanding that it is not a good value and a less sophisticated cooking experience than elsewhere.

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. Wine Tasting and Tour of The Most Beautiful Cellar in the World

Via di Collazzi, 7, 53045 Montepulciano SI, Italy Umbria Con Me Day Tours
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4.9 based on 23 reviews

A visit to this Cellar is a voyage in time and history: here is the essence of the sweet Tuscan earth, the wine, that they already took care of, worshiped and consumed in happiness and joy, with passion and tenacity our distant ancestors, the Etruscans, some centuries earlies than the Christian era.

Inclusions: Cellar tour, Bruschetta with extra virgin olive oil, Wine tasting

Exclusions: Transportation to/from attractions

Reviewed By D1271ETdianaw

We had a fascinating morning with Alessandra, exploring Assisi and learning about its history. It's such a beautiful place, and Alessandra made it come alive for us. The 'Umbria con me' attention to detail was superb, and booking lunch for us at a local restaurant afterwards was a lovely touch.

8. Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Tours of Tuscany
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4.9 based on 27 reviews

This full-day tour will bring you a taste of the complex, full-bodied Brunello reds that make this region every wine lover’s dream. We will pick you up at your hotel & take you to some of the lesser-known vineyards with high-quality wines. After your first tasting, take some time to explore the hilltop town of Montalcino, where we will visit a second Brunello winery. Then we will continue to Pienza, a UNESCO World Heritage Site & a unique example of the ideal city according to Renaissance architecture. Then one last stop in the small town of Montepulciano, where you can taste the exquisite Nobile di Montepulciano wine & meet the winemakers that make the magic happen. Enjoy a special lunch featuring local specialities. Pick-up & Drop-off at your accommodation 3 wine tastings at boutique wine cellars Lunch with wine pairings & local specialities Visit Pienza & Montepulciano Small group: limited to 8 guests Don’t drive while you wine & dine! Let us take care of everything.

Inclusions: 3 Winery tour and tasting, Pairing lunch at a historic winery, Bottled water, Air-conditioned vehicle, WiFi on board

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

9. Cities, Cheese and Wine Tour in Pienza & Montepulciano

Tours of Tuscany
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4.8 based on 17 reviews

Pienza and  Montepulciano Wine Tour - Experiences 1 day exciting trip in Valdorcia Tour Length: 7/8 hours. Dates: Every season.  Days of Week: Everyday. Departure Point: From your accommodation - pick-up and drop-off in Florence , Siena , Pienza , Montepulciano, Chianti Area or South of Siena province. Departure Time: From Siena or nearby 09.00/09.30 AM – Florence 08.00AM Note: During this excursion transport will be made in a Mercedes 9 seats minivan which offers the maximum comfort, with air-conditioning, large panoramic windows and comfortable seats. Unless you don't specify you want to remain private, is possible to be joined with some other people in the party ( maximum 1 van ) Popularity: *****  (best seller wine and food tour in Tuscany)

Inclusions: Tour and tasting in an historic wine cellar, from the oldest and famous of the Brunello area and famous worldwide. Visit the town of PIENZA - Cheese Tasting Light Lunch at a HISTORIC WINERY IN MONTEPULCIANO DOWNTOWN Visit of a third winery in the Nobile di Montepulciano Area Area Bottled water Lunch Wine Tastings, Lunch, Snacks, Alcoholic Beverages, Air-conditioned vehicle, WiFi on board

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

10. Full-Day Winery Tour in Montepulciano with Tasting and Lunch

Tours of Tuscany
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4.8 based on 34 reviews

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run, boutique vineyards with high-quality production. Get picked up at your hotel in Siena (or anywhere within Siena province) & venture into the Tuscan countryside with a small group and a local guide Together you’ll visit two vineyards in the rolling hills of Tuscany, both boutique wineries specializing in Brunello reds. From there you’ll head to the enchanting Medieval town of Montalcino, where you’ll visit two historic wine cellars. After a leisurely walk within Montalcino’s fortress walls, it’s off to Pienza, a UNESCO World Heritage Site that offers the best panorama of the Val d’Orcia, along with high-quality artisan crafts & unique pecorino cheese. Lunch will take place in yet another charming town, Montepulciano, where you can enjoy traditional Tuscan delicacies in a Cathedral-sized wine cellar.

Inclusions: 3 Visit and wine tasting , Lunch Wine Tastings, Bottled water, WiFi on board, Air-conditioned vehicle

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

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