The 10 Best Walking Tours in Province of Arezzo, Tuscany

May 27, 2021 Carley Gatson

The province of Arezzo or Arretium (Italian: provincia di Arezzo) is the easternmost province in the Tuscany region of northern Italy. Its capital is the city of Arezzo. The province is bordered by the regions of Marche, Emilia-Romagna, Umbria, and the provinces Siena and Florence of Tuscany. It has an area of 3,235 square kilometres (1,249 sq mi), a total population of about 347,000 in 37 comuni (singular: comune), and a density of 107.2 people per square kilometer.
Restaurants in Province of Arezzo

1. Wine Tasting and Tour in an Organic Winery

Podere di Pomaio • Green Winery, 19 Località Pomaio, 52100 Arezzo AR, Italy Podere Di Pomaio Green Winery
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5.0 based on 21 reviews

Nestled 3mi (5 km) from the city center of Arezzo, you're just a 10 minute drive from this unique wine tasting opportunity. One of the 14 most beautiful wineries of Tuscany, thanks to its unique wine cellar in bio-architecture, and the 'Think Green' philosophy for a sustainable and environment-friendly production. The tour offers the chance to visit vineyards, wine cellar and taste 3 wines matched with Tuscan cold cuts and pecorino cheese. It is also possible to have lunch together with the wine tasting.

Inclusions: Food tasting, Wine tasting, Guide

Exclusions: Hotel pickup, Transportation to/from attractions

Reviewed By KSpritzz

10/10 stars for Villa Leopoldina and Podere di Pomaio winery! We live in Italy and can say confidently this was the best stay we've ever experienced. Every detail was intentionally though through for guests, and the sustainable winery experience topped everything off. The private pool, stylish villa, amazing floor plan and so much more.. We cannot wait to return!

2. Cortona Private Guided Tour

Cortona Piazza Garibaldi, 52044 Cortona, Province of Arezzo, Italy Umbria Con Me Day Tours
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5.0 based on 1 reviews

Cortona has become very popular several years ago thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is set in Cortona; the protagonist immediately falls in love with the town, its people, and villa Bramasole that she purchases and fixes up.

Inclusions: Local guide

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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.

3. Arezzo Art and Wine

TerraPura, Via Cavour, 84, 52100 Arezzo AR, Italy TerraPura
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5.0 based on 1 reviews

Discover the thousand-year old cultural heritage of Arezzo, the hidden gem of Eastern Tuscany. We will walk you through all iconic places of our home town for a fantastic journey back in time: the Roman Amphitheatre, the Medieval Piazza Grande and its tangle of narrow lanes, the Medicean Fortress, the gothic Cathedral, the world-renowned frescos by Piero della Francesca and the mesmerising Casa Museo Ivan Bruschi. We will end our tour in an organic winery in the hills just above the old town for a unique wine tasting experience. You will get the chance to taste Arezzo’s best wine accompanied by some tasty antipasti (vegetarian/vegan variations upon request) as the sun slowly sets over the vineyard

Inclusions: Your wine tasting experience at the local winery is included in your participation fee!

Exclusions: Entry ticket to the Basilica di San Francesco

Reviewed By emilders

Me and three friends did TerraPura's Winetastic tour and it was incredible! Chris and Mirko took us to two distinctly diverse and unique wineries- one of the oldest Wineries run by a woman and her 2 daughters and the other set in a castle atop one of the most breathtaking views I think I have ever seen. Chris and Mirko were welcoming and very knowledgeable about the cities of Montalcino and Montepulciano- they even took us up to the top of Montalcino city hall for yet another breath taking view! Without a doubt one of my favorite days in Italy.

4. Siena, Cortona, Montepulciano & Val D'Orcia from Florence - Semi private tour

Via Nazionale, 149, 50129 Firenze FI, Italy Italy on a Budget Tours
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5.0 based on 7 reviews

Explore in the comfort of a 8 seat van the most beautiful Tuscan towns made famous through films together with a passionate local driving guide. Enjoy lunchoverlooking the rolling hills of Montepulciano while tasting famous wine. Wander the winding streets of Cortona walked by Diane Lane in "Under the Tuscan sun", watch out for the vampires of the Twilight saga " New Moon" in Montapulciano and taste the famous Noble of Montepulciano wine. Explore the locations made famous by Michelle Pfieffer in "A Midsummer night's dream" and Ralph Fienes in " The English patient". Spot the iconic rolling hills of Tuscany from " Letters to Juliet" and enjoy a taste of the local lifestyle by sampling fine local wine, cheese and other products from the region.

Inclusions: Light lunch in a local winery including 2 wine tasting including the famous " vino nobile di Montepulciano", Wine and cheese tasting in a 13th century cellar, Air-conditioned vehicle, Orientation walk of Montepulciano and free time, 1h free time to explore Cortona, Orientation walk of Siena and free time

Exclusions: Gratuities, Pick up / Drop off

Reviewed By amrutaprasad029

Beautiful experience... We had booked the tour online and it was better than expected ... Beet well planned too ... And great guide

5. Inside Renaissance

TerraPura
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5.0 based on 1 reviews

If you think that Florence is the cradle of Renaissance we will prove you wrong with this tour! Take a journey through the hidden birthplaces of art & crafts genius: we will bring you to Michelangelo’s home town Caprese (not to be mixed up with the homonymous tomato-and-mozzarella dish!). the picturesque hill town of Anghiari we will walk you through the natural backdrop of Leonardo’s lost masterpiece The Battle of Anghiari. Next, you will discover Antiche Officine Busatti, a mesmerising bottega from 1860, where old textile craftsmanship is still alive and transmitted to the next generations. The tour then continues to the town of Sansepolcro, where you have the choice to visit either the Museo Piero della Francesca or Museo dell’Erboristeria, located in a fascinating 19th century Tuscan villa. This tour is all about the secrets of Tuscan genius.

Inclusions: All Fees and Taxes

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Reviewed By emilders

Me and three friends did TerraPura's Winetastic tour and it was incredible! Chris and Mirko took us to two distinctly diverse and unique wineries- one of the oldest Wineries run by a woman and her 2 daughters and the other set in a castle atop one of the most breathtaking views I think I have ever seen. Chris and Mirko were welcoming and very knowledgeable about the cities of Montalcino and Montepulciano- they even took us up to the top of Montalcino city hall for yet another breath taking view! Without a doubt one of my favorite days in Italy.

6. Private Full-Day Tour of Assisi and Cortona from Florence

Ciao Florence Tours and Travels
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4.6 based on 9 reviews

Relax on this private, full-day tour of Assisi and Cortona. Enjoy the personalized attention of your private driver and discover the place where St. Francis and St. Clare were born and visit the wonderful hilltop town of Cortona. A relaxing day trip between Umbria and Tuscany at your own pace! Hotel pickup and drop-off from Florence is included with a driver.

Inclusions: Hotel pickup and drop-off, Mercedes vehicle, Speaking driver, Free time in Assisi and Cortona, Bottled water, Wi-Fi

Exclusions: Food and drinks, Local guides in Assisi and Cortona

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.

7. Assisi and Cortona Day Trip from Florence

Piazzale Montelungo, Firenze FI, Italy Ciao Florence Tours and Travels
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4.1 based on 126 reviews

Discover the enchanting hilltop towns of Assisi and Cortona on a day trip from Florence, led by a local tour leader! Walk around Assisi, and learn about the life of St Francis of Assisi on visits to the Basilica of San Francesco and the Convent of Santa Chiara. Stop to admire the 9th-century church in Santa Maria degli Angeli before continuing to the Tuscan town of Cortona for some free time to explore.

Inclusions: Journey by fully fitted GT Coach, Expert multilingual escort, Assisi tour with professional guide, Stop for panoramic pictures at Passignano sul Trasimeno, Entrance fee to St Francis'Basilica, Entrance fee to Santa Chiara Church, Entrance fee to Santa Maria degli Angeli Church

Exclusions: Hotel pickup and drop-off, Food and drinks, Gratuities

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.

8. Arezzo private guided walking tour

Piazza Del Duomo, 3, 52100 Arezzo AR, Italy Arezzo Faberest
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4.0 based on 1 reviews

During this 2.5-hour private tour your expert guide will take you through the most important and interesting sports in the beautiful city Arezzo.Although still far from most of the touristic flows, this mid-sized Tuscan city is truly beautiful and its his

Inclusions: Expert tour guide, Private tour

Exclusions: Entrance fees to museums/attractions (in case you decide to visit any of them in particular), Entry/Admission - Santa Maria della Pieve, Food & drinks

9. Arezzo Walking Tour with Professional Guide

Via Giuseppe Pietri, 41, 52100 Arezzo AR, Italy Umbria Con Me Day Tours
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4.0 based on 1 reviews

Sitting on top of a hill at the junction of the 4 valleys that compose its province, Arezzo was a great Etruscan and Roman city. In the Middle Ages Guido Tarlati, important Bishop in the XIV century, turned the city into a great cultural and artistic centre.

Inclusions: Professional guide

Exclusions: Gratuities

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.

10. Taste of Italy Food Tour to Chianti and Umbria from Rome

Via Giovanni Amendola, 32, 00185 Roma RM, Italy Green Line Tours
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3.8 based on 246 reviews

Discover the foods, wines and hill towns of Tuscany’s Chianti wine region and Umbria on this engaging full-day tour from Rome! Accompanied by an expert local guide, travel through Tuscany’s rolling countryside and visit the lovely medieval town of Cortona, with time to explore its cobbled lanes and absorb its old-world atmosphere. Enjoy a tasty regional lunch at a rural farmhouse restaurant, and wind through the vineyards of Chianti to the hill town of Montepulciano. Here, sample some delicious local wines at a traditional cellar before heading back to Rome.

Inclusions: 4-course lunch, Local guide, Transport by air-conditioned coach (maximum 50 people), Hotel pick-up (only for certain hotels located in central Rome - to be reconfirmed by the supplier after booking)

Exclusions: Gratuities, Drinks with lunch (available to purchase)

Reviewed By nth1234

Wonderful tour of St Peters finishing with the cistine chapel with Alessandro. Once again this guide was first class in his delivery and knowledge of the place. Sean the boss of Angel Tours was excellent with his communications and I thoroughly recommend this company, will definitely use again.

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