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Cortona, AR

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Cortona Wine Tours

5.0 (2 reviews)
Open • Open 24 hours

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3 years ago

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We Drive You Tuscany

We Drive You Tuscany

4.9(22 reviews)
52.6 km

Absolutely incredible service -- Thomas went above and beyond!…read more We had the pleasure of having Thomas as our driver in Siena, and we honestly couldn't recommend him enough. It was a Sunday in Italy and we were completely stuck with no transport. Thomas arrived in a lovely, air-conditioned van, helped us with our bags, and immediately went out of his way to make sure we had the best possible experience. As soon as we got in the car, he told us all about Montepulciano -- the best vineyards to visit, what prices to expect, and how to get around. We hadn't booked anything, but Thomas contacted his friends and organised everything for us. He even took us to our hotel, waited patiently while we checked in, and never rushed us. He then arranged a taxi to collect us after our vineyard tour and even negotiated the price for us -- something we never asked him to do! At the vineyard, he personally walked us in and introduced us to his friends. Thomas truly saved our day and turned what could have been a stressful experience into one of the highlights of our Italian trip. He was incredibly kind, patient, generous, and genuinely wanted us to have the best experience possible. If you have the option to book this service, do it! And if you get Thomas as your driver, you're incredibly lucky. Thank you so much, Thomas, for making our experience so special!

Tomas was very knowledgeable of Assisi, Cortona, and all of Italy. He also spoke English very well…read moreand was very friendly. He was an excellent and very safe driver and knew the area very well. My wife and I highly recommend him as a driver and tour guide.

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We Drive You Tuscany
We Drive You Tuscany
We Drive You Tuscany

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Podere di Pomaio - outdoor gathering area at villa

Podere di Pomaio

5.0(2 reviews)
24.0 km

We rented a villa at Podere di Pomaii for a family vacation. It is a perfect property for such an…read moreescape - very close to Arezzo but on a hill with views that feed your soul, breezes that sing, and villas that offer all you need to enjoy your stay. Plus it is a green winery that produces a delicious variety of wines and olive oil. The winery tour and tasting alone would be worth the trip to this property. Great wine to drink, wine knowledge to feed your mind, and enough artisan food samplings to feed the most robust appetite. The villa we rented had 6 bedrooms each with its own bathroom. All beautiful in their simplicity and generous space. The villa is designed and maintained to the highest degree. There are inside and outdoor gathering spaces to join together for a meal, relax your way to the beginning of the day, or laugh, talk, and drink until the calendar page flips over. There is even a pool to remove the heat of the day. Everyone we met from owners to tour guide to cleaning staff have the nicest and most pleasant demeanors - helpful, friendly, and welcoming.

Podere Di Pomaio is a beautiful winery that is as "green" as it gets! My family and I had a tour of…read morethe vines and cellar, followed by an incredible lunch and tasting. Iacopo, the owner and winemaker, and our tour guide Bonella (spelling?) were very welcoming, kind and informative. It's an incredibly beautiful location with wine that reflects the beauty in which it is made. Several of us came home with multiple bottles. Perfect location for an event/wedding/reunion, or just for tasting delicious, organic wine at its best!

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Podere di Pomaio - Vineyard

Vineyard

Podere di Pomaio - Tasting with light lunch in the tasting room

Tasting with light lunch in the tasting room

Podere di Pomaio - Iacopo and Marco, the 2 founders of Podere di Pomaio * Green Winery

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Iacopo and Marco, the 2 founders of Podere di Pomaio * Green Winery

Wine Tours in Tuscany with Italy and Wine - Exaiming the wine color

Wine Tours in Tuscany with Italy and Wine

5.0(120 reviews)
80.3 km•Santa Croce

TL;DR - this tour is a delight to those who truly care about the entire winemaking process,…read morehistory, and culture. My wife and I planned our dream vacation to Italy with a focus on food and wine. Our time in the Florence area mandated the intentional trip to my (and now OUR) favorite winemaking area - Montalcino. We spent months planning and researching and came across this wonderful local company - "Italy & Wine Tours." Upon review of their website we were captivated by their intentionality to have the time be an intimate and thoughtfully curated all day adventure from Florence through the Chianti region, into the romantic hills of Val d'Orcia, and onto the hillside of Montalcino. To our delight - on the day of the trip we found that we were the only couple who signed up to go that day. Our tour guide Nicolò (who was INCREDIBLE and has formal WSET training/certification) was joined by the delightful daughter (Ippolita) of the company's owner. It was the best experience traveling with them. From the moment we were introduced to the moment we were dropped off at the end of the day we never stopped talking, laughing, sharing stories, and learning more about our favorite shared passion - Italian wine. Now onto the WINE! I won't spoil your trip with too many specifics, but our tour began from the beginning - how did Brunello di Montalcino come to be? We toured the streets of Montalcino and immersed ourselves in local history, tradition, etc. following the city, we were off to the first winery. The first winery focus was on the (traditional) aspects of Brunello. The centuries old family fortress made it abundantly clear. It was an idyllic location through the cellars, learning about the soil, property history for pilgrimages, ancient Rome, and crusades. We sampled 4 wines produced by the site which trended towards elegant, refined, and approachable. During the tasting we were blessed with a delicious and traditional private Italian lunch. Afterwards we went to the second winery which was slightly more modern (in winemaking style) but nonetheless a delight. We dove deeper into soil composition, weather, aging conditions, and micro-factors. The wine at the second location was big, bold, wonderfully complex and personally my preferred style. We concluded our time thanking our hosts and guides over and over again with multiple bottles in hand to bring home and shared with our family. We sincerely hope you (the reader) get to experience Italy and Montalcino in the same way we did. Personal highlights / Why choose this company: - historic, locally/generational owned wineries - not large corporate productions. - 2 production styles helped compare/contrast the same type of wine helping me choose future bottles more accurately. - The tour guides / owners. They care about you, and hospitality is so genuine. Please support companies like this. Thank you so much Nicolò and Ippolita. You are forever in our hearts and we hope our paths cross again in the future!! *David & Kenzie (Seattle, WA)

Our Montepulciano wine tour was one of the highlights of our trip to Italy, and much of that was…read morethanks to Niccolò. From the moment we left Florence, he transformed what could have been a simple drive into a fascinating journey through Tuscany. We spent the day discussing Italian history, culture, education, and different perspectives on life, which added tremendous depth and meaning to the experience. Niccolò is knowledgeable, engaging, and genuinely passionate about sharing his country with visitors. By the end of the day, he felt more like a friend than a guide. The wineries themselves were equally impressive. We especially appreciated visiting family-owned vineyards where generations of winemakers have preserved traditions while producing exceptional wines. The hospitality was warm and authentic, and each winery offered a unique glimpse into the rich heritage of the Montepulciano region. The wine tastings were outstanding, but it was the stories, family histories, and personal connections that made the experience truly memorable. This tour provided far more than wine tasting--it offered an opportunity to experience the culture, people, and traditions of Tuscany in a meaningful way. If you are considering a wine tour from Florence, I highly recommend this experience, and if you are fortunate enough to have Niccolò as your guide, you are in for a remarkable day. Thank you, Niccolò, for making our day so special and for sharing your knowledge, insight, and enthusiasm with us. We will remember this experience long after the last bottle of wine is gone.

Photos
Wine Tours in Tuscany with Italy and Wine - Shiva our fabulous guide and group in San Gimignano

Shiva our fabulous guide and group in San Gimignano

Wine Tours in Tuscany with Italy and Wine - San Gimignano square

San Gimignano square

Wine Tours in Tuscany with Italy and Wine

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Cortona Wine Tours - winetours - Updated October 2026

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