May 29, 2023

The best wine tastings & authentic dining in Chianti, Italy

FILED IN: Italy, Travel

Welcome to the Chianti region of Tuscany, where vineyards and picturesque landscapes stretch as far as the eye can see. Nestled in the heart of Tuscany, Italy, this enchanting destination offers unforgettable experiences for those seeking delicious wine tastings and dining adventures. I’m delighted to unveil the best wine tastings & authentic dining in Chianti. Prepare your palate for an extraordinary adventure, where every sip and bite tells a story of passion, tradition, and unparalleled gastronomic pleasure.

Note: I strongly advise you to make advance reservations to ensure a smooth experience while you’re exploring the best wine tastings & authentic dining in Chianti and ensure a smooth experience. Certain establishments have a mandatory reservation policy in place.

Looking for more on the Tuscany region? Here are all of my guides. I have also included a map with all of the locations pinned. Feel free to save it!

The best wine tastings in Chianti

Let’s explore the best wine tastings and authentic dining in Chianti. First up, the best wine tastings in the area. Indulge in exceptional wines accompanied by delectable food pairings. Immerse yourself in the region’s renowned wineries and savor locally sourced cuisine. A remarkable journey awaits, celebrating the fusion of wine and gastronomy.

Poggio Amorelli

Founded in 1997 by Tuscan winemaker and agronomist Marco Mazzarrini and his wife Adriana, Poggio Amorelli farm is a haven located in the heart of Chianti Classico near Castellina in. Chianti. This idyllic setting allows visitors to immerse themselves in nature while savoring the estate’s wines and authentic Tuscan products. They have since expanded to three other estates – one in the Tuscan Maremma, another in the Chianti area, and a small balsamic vinegar cellar in Modena. In addition to a remarkable range of IGT and DOCG wines that honor Tuscan traditions, they produce Extra Virgin Olive Oil, Grappa, and exquisite Balsamic Vinegar, aged to perfection.

We decided to combine our wine tasting with a lunch. This is a wonderful way to discover the pleasure of the local cuisine. The dishes are prepared with high quality products – handmade pasta with eggs from their chickens, fresh truffles, seasonal vegetables from their organic garden, genuine sheep’s milk cheeses, homemade desserts and more. If you happen to be traveling to the area in the warmer months, you can request a spot on their panoramic terrace which overlooks the breathtaking Tuscan landscape. We opted for a table inside which was wonderfully intimate.

This “light lunch” included bruschette, farro, salumi, a choice of 3 pastas (I went with the Tuscan ragu), a small salad, a cheese tasting and dessert + of course a tasting through their wine, EVOO, balsamic and grappa production!

We ended up going home with: EVOO, balsamic, Chianti Classico Riserva & a Sparkling Rosé

Querceto di Castellina

Querceto di Castellina has been in the family since 1945 when a love for the land and this historical estate led Guido Masini, originally from Florence, to acquire it. The over 200-acre property became a countryside retreat for his family but Guido’s entrepreneurial spirit kicked in starting a few businesses from selling grapes to farming pigs. He eventually leased out the land for a few decades, but his daughter Laura took back the management of the estate in 1989.

The best wine tastings & authentic dining in Chianti, Italy – Querceto di Castellina

Working together with her husband Giorgio Di Battista, an architect, Laura restored the 15th century structures on the estate, transforming them into an agriturismo with vacation apartments. She converted the rest of the property into a working farm with olive groves and focused on improving the vineyards. Shortly after, she began her Tuscan cooking classes. It wasn’t until 1998 when their eldest son Jacopo began working for the estate and founded the winery.

There are a handful of tasting experiences offered on property, but we decided to go with the premium wine tasting lunch and tour, which includes antipasto, a pasta course and a traditional Tuscan main dish + a side and dessert.

We ended up going home with: Laura, a Chianti Classico

Fattoria Casa Sola

Casa Sola welcomes visitors with its rustic charm and inviting ambiance. This picturesque farmhouse offers a haven of comfort, boasting spacious apartments that provide a home away from home. Surrounded by a stunning garden, complete with a refreshing swimming pool and breathtaking panoramic views, Casa Sola is a sanctuary of tranquility.

With a deep commitment to quality and a profound respect for the environment, Casa Sola produces an impressive array of wines that reflect their “traditional and innovative” approach. Every bottle crafted is a labor of love, as they tirelessly strive for excellence and the highest standards.

While our visit was met with rain, depriving us of the opportunity to stroll through their fields, we were captivated by the glimpses we caught of the property and its surroundings. Even under the grey skies, the beauty of Casa Sola shone through, leaving us longing to return and fully immerse ourselves in its splendor.

Indulging in a tour and tasting experience with a delectable snack at Casa Sola proved to be a delightful choice, allowing us to explore and savor their exquisite wines while immersing ourselves further in the wonders of the Chianti region.

We ended up going home with: Chianti Classico & Vin Santo

Castello di Ama

Ama is a historic estate in the Chianti region with a rich past dating back to the Holy Roman Empire. The original castle was destroyed during the Aragonese invasions in the fifteenth century. However, in the early 1700s, new dwellings were constructed using the same stones, resurrecting the spirit of the castle.

In the early 1970s, Tomaso Carini and his friends embarked on a journey to revive the estate. They replanted the vineyards and built a modern fermentation cellar, setting an innovative example for the area. In 1982, Marco Pallanti, a talented Florentine agronomist, joined as the esteemed winemaker. In 1993, Lorenza Sebasti, Lionello’s daughter, took over the management of Ama. Today, Lorenza and Marco continue to share a passion and unwavering vision for Ama. They have created a legacy that combines history, innovation, and a commitment to producing exceptional wines in the heart of Chianti.

Make sure to schedule your experience ahead of time! Here are their offerings that don’t include food. We opted for one that included a tour of the property, featuring art installations and delightful wine and olive oil tastings + a delicious pairing lunch.

The best wine tastings & authentic dining in Chianti, Italy – Castello di Ama

Following our tour, we ascended to their restaurant located upstairs, where we savored a delightful lunch on the patio, offering picturesque views of the sprawling hillside.

We indulged in a scrumptious feast consisting of pasta, meatballs, and a delectable serving of wild boar – a renowned local specialty. The recommendation to try the wild boar came from a fellow traveler seated beside me on my inaugural visit to Italy in 2018, and we were not disappointed by its exquisite flavor. For dessert, we relished a citrus cheesecake adorned with succulent blackberries + a delightful trio of coffee ice cream scoops on the side.


This family-owned winery is located near the medieval village of Montefioralle in Greve. They specialize in winemaking and also produce high-quality extra virgin olive oil. The Sieni family takes great pride in their small-scale production, paying close attention to every detail to ensure the highest quality. They are committed to sustainability and obtained organic certification in 2019.

The best wine tastings & authentic dining in Chianti, Italy – Montefioralle

Amedeo Gherardini wrote the following from the Castle of Monteficalle (now Montefioralle) to his friend Francesco di Marco Datini on November 27, 1401 – 

Da poi ch’io fui qua, ò asagiato più vini, e non truovo cosa che mi piaccia altro che questo che vi mando e parmi il migliore che ci sia…e se dovete tor vino, cogliete questo che è sempre mai el migliore che ci sia”

“Since I’ve been here, I’ve tasted more wines, and I don’t think I like anything other than this one that I send you and I give you the best there is…and if you have to drink wine, take this one that is always the best there is.”

Renato Sieni, after retiring in 1964, established Montefioralle winery by renting a vineyard from the Montefioralle village’s monastery. He planted new vines and produced the renowned “S. Stefano a Montefioralle” wine, making Chianti Classico to benefit the S. Stefano parish. In the late 70s Fernando, Renato’s son, developed a passion for winemaking and joined his father. In the 1990s, when the church administration decided to sell the farm, the Sieni family promptly acquired it, marking a new chapter in their winemaking journey.

Montefioralle exclusively offers tastings by appointment. Visitors can indulge in a delightful range of their wines, including Chianti Classico, Chianti Classico Riserva, IGT, and Vin Santo. For an enhanced experience, guests have the option to savor the wines alongside a delectable light snack, which we obviously chose to do! On select days, they also provide the opportunity to book a special visit featuring a vertical tasting of five vintages of their esteemed Chianti Classico Riserva. I’m already looking forward to returning for this extraordinary experience!

Wine Tasting in Panzano at Accademia del Buon Gusto

You may already be familiar with Panzano due to its association with Dario Cecchini’s famous butcher shop, which gained recognition through its feature on the popular Netflix series, Chef’s Table. However, during our visit in 2022, Walter and I found ourselves somewhat disappointed with our experience. I assume the post-pandemic era has brought about changes, and the place has become more crowded and popular, resulting in a different vibe than what was portrayed on television. Nevertheless, it’s important to remember that television often presents a heightened reality. I don’t mean to discourage you from going, but I suppose we set our expectations too high. On the bright side, the food and wine were generally good.

Note: Unfortunately, I learned that the wine shop I am about to mention is now closed due to the passing of Stefano. However, I still feel compelled to share my experience because his shop was greatly cherished in the Chianti region. I feel incredibly fortunate that my mom and I had the opportunity to meet him and embark on a delightful tasting journey at his establishment.

We were in Panzano because Marta and Bernardo of Selvabella B & B recommended this spot! They told us it is a unique experience and warned us that we would probably be there for 3 hours. We tasted through 20+ wines ranging from Chianti Classico, Reserva, and IGT or Super Tuscan. The tasting is free, but we obviously left with leave with a couple of bottles. Stefano, the owner of the shop, was a wonderfully cooky knowledgeable man who told stories as he poured.

The best authentic dining in Chianti

If you’re looking for more of an interactive dining experience, check out this post about my favorite cooking classes in the region!

Note: House wine in Italy rarely disappoints! This is a great way to save some money if you plan on eating out for most meals! Even deciding to go with house wine for lunch and a nicer wine at dinner can make a huge cost difference!

Azienda Agricola Ammirabile

As we embarked on our journey back to Bologna, we yearned to conclude our trip on a high note. When I stumbled upon the glowing 5-star reviews of Azienda Agricola Ammirabile on Google maps, I knew without a doubt that we had to book a tasting and lunch. Upon our arrival, we were greeted with warmth and genuine hospitality by Grazia, who skillfully crafted an extraordinary meal for us to savor.

Driven by their deep love for nature, Giovanni and Grazia were inspired to establish a close connection with the natural world, embracing its rhythms and principles. Thus, in the 1980s, the Ammirabile farm was born in the heart of Tuscany. Today, it remains a family-operated business, with Giovanni, Grazia, their daughters and their husbands actively involved in its daily operations.

Nestled amidst the breathtaking Chianti hills, the farm spans across 20 meticulously tended hectares. Six of which are dedicated to vineyards, 10 of which have flourishing olive trees. The remaining area comprises a thriving woodland, home to the diverse Tuscan wildlife. Giovanni and Grazia’s unwavering commitment ensures that the farm’s wine and oil are exclusively crafted from their own hand-picked grapes and olives, with close attention paid to every stage of production, from field to bottle. This meticulous approach guarantees the creation of exceptional products that beautifully embody the distinctive characteristics of the region’s terroir.

Our epicurean journey commenced with an enticing starter, followed by Penne with freshly-harvested artichokes from their very own garden, then a by a luscious Eggplant Parmesan. The grand finale arrived in the form of a divine homemade cake. We went home with some of their olive oil, a delightful rosé, and a bottle of their esteemed Chianti Classico wine. You can request to book here!

Ristorante Pestello

Located in the heart of the Chianti countryside, the historic Antico Pestello Restaurant has origins dating back to the 1800s. They have a diverse menu of traditional dishes featuring black truffles, porcini mushrooms, and Pecorino cheese, an extensive wine selection, and exceptional grilled meats cooked over a wood-burning fire.

The best wine tastings & authentic dining in Chianti, Italy – Ristorante di Pestello

The intimate and inviting ambiance of the converted stable rooms preserves a timeless charm, while the summer terrace offers a romantic al fresco dining experience. Since 1994, the Martinucci family has lovingly operated the restaurant, with Teresa and Maria Pia’s culinary skills in the kitchen and Federico’s attentive care in the dining room, curating an experience that makes every guest feel right at home.

We started with the Assorted Antipasto Plate, made up of deliciously prepared cured meats, cheeses and bruschette. The highlight of our meal was undoubtedly the Steak with Chianti Sauce, a delectable combination that left a lasting impression. For dessert, we ordered the exquisite panna cotta, the traditional torta della nonna, and a decadent chocolate cake that rivaled the renowned offering from Mariposa Trattoria in Bologna. The only thing missing was some mascarpone. IYKYK

Ristoro di Lamole

Paolo and Filippo fell in love with Lamole in 1993 – the colors, sunsets, and vineyards. Their mission: to make Lamole known through kindness, top-quality ingredients, and cellar that everyone can appreciate. After 30 years, Lamole’s magic still captivates them.

The best wine tastings & authentic dining in Chianti, Italy – Ristoro di Lamole

Chef Ettore blends innovation and tradition, creating dishes that harmoniously merge simplicity and refinement. In 2019, Paolo’s daughter, Marta joined the team, infusing the company with fresh energy and ideas. Lamole became one of our favorite meals during my first trip to Tuscany with my mom – from the stunning view to the impeccable service and inventive Tuscan dishes, it was sheer perfection. When I returned with Walter, we were equally impressed. Anything you order here will be supreme!

For our first dishes, we savored the delectable Warm Red Onion Pudding infused with fragrant truffle. Additionally, we enjoyed the Black Venus Risotto accompanied by fresh vegetables, which added a vibrant touch to the dish. Lastly, we couldn’t resist trying the exquisite Ricotta & Pear Ravioli, with its creamy filling and subtle sweetness.

Onto the second dishes! We enjoyed a succulent Roasted Tuscan Chicken stuffed with dried prunes, served atop a bed of creamy mashed potatoes, as well as the daily special of a refreshing Artichoke Salad with creamy burrata cheese.

Osteria Volpaia

Osteria Volpaia has three inviting private dining rooms and a sprawling terrace that leaves guests in awe. Our dining experience on the gorgeous terrace was nothing short of delightful, as we were captivated by the stunning surroundings while savoring our meal. The culinary artistry displayed at Osteria Volpaia was evident in every dish presented to us, as each one was meticulously plated with a visual appeal that matched its exceptional taste.

One of the defining features of Osteria Volpaia is its commitment to embracing the seasons and celebrating the abundance of fresh and local ingredients. This dedication is reflected in their menu, which undergoes changes throughout the year. With each season’s arrival, Osteria Volpaia seizes the opportunity to showcase the best flavors of the moment by utilizing the freshest and most readily available ingredients. Many of which are sourced from the town’s own organic gardens. I love this conscious approach – harmonizing with nature’s rhythms and making it easy to indulge the senses with the vibrant flavors of the region.


Bar-Ucci is owned by Paola Barucci, who was born in and has always lived in Volpaia. She opened it in 2002 for her mom and dad, to thank them. Inside the bar you will find photos that retrace their family history. Nowadays, her mom Gina help by making cakes.

The best wine tastings & authentic dining in Chianti, Italy – Bar Ucci

Paula has always worked in the wine world, which has helped her appreciate her beloved Chianti even more. Her wine list includes different areas of Tuscany, from producers she knows personally.

“The best compliment my clients pay me is when they tell me they feel at home and I never expected such a success of positive comments, which is why I would like to thank everyone with my affection and esteem.”

“The Tuscan and Chianti tradition of food has very ancient roots, but from the Etruscans to the present day the recipes have not changed much. Simplicity, a few predominant spices, bread without salt and the splendid cold cuts and cheeses are still the basis of eating today daily.”

Walter ordered a beer and I had a spritz, then we shared the Cacio e Pepe and Wild Boar Pappardelle. Of course we couldn’t leave without trying Gina’s cake! It seems you can’t go wrong with anything on the menu and we definitely felt at home 🙂

Curious about Volpaia? I wrote a whole post about this medieval village here.

Planning a trip to Italy? Get inspired by the rest of my Italy content!


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Growing up near Pasadena, CA, my creativity blossomed as I delved into the LA food scene, food styling, photography, and storytelling. Now, I curate content centered around food, beverage, and travel, while indulging in hobbies like thrifting. Italy holds a special place in my heart, where I found love and embarked on a new chapter in Bologna. Join me on this creative journey of food, travel, and love.