Best things to do in Chianti area,Tuscany

Chianti Tuscany

Chianti is  a captivating region nestled in the heart of Tuscany, spanning across Florence, Siena, and Arezzo. Its landscape boasts undulating hills adorned with quaint villages, ancient strongholds, churches, and rustic estates.

To experience Chianti is to immerse oneself in its evocative ambiance, exploring charming towns, unwinding amidst its pastoral vistas, and indulging in the pleasures of exquisite cuisine and fine wine. Nature takes center stage in Chianti, a tapestry interwoven with historical landmarks, cultural treasures, museums, and vibrant traditional celebrations.

This captivating environment isn’t just a haven of beauty and heritage; it also boasts distinctive gastronomic delights and world-famous culinary offerings. At the forefront stands its illustrious wine production, where the Chianti wine region reigns supreme among the globe’s most esteemed viticultural areas. 

We hope you’ll find our recommendations on the best things to do in Chianti useful in planning your holiday in one of the most charming areas in Tuscany.

How to get to Chianti

Car to Chianti

If you prefer flexibility and the ability to explore the region at your own pace, renting a car is an excellent choice. The drive through the rolling hills of Chianti is a scenic experience in itself. From Florence, take the SR222 road, famously known as the “Chiantigiana” route, which meanders through the Chianti Classico wine-producing region. From Siena, follow the same SR222 route for a delightful journey.

Public transport to Chianti

If you’d rather not drive, you can use public transport. Trains and buses are available from Florence and Siena to towns in Chianti like Greve, Castellina, and Radda. However, keep in mind that public transport options may be limited in certain areas, and you may need to rely on local buses or taxis to reach specific destinations within Chianti.

Plane to Chianti

The easiest way to travel to Chianti by plane is via Pisa International Airport.

Rent a car Tuscany

Rent a car Tuscany

The best way to experience Puglia and the surrounding area is to rent your own car! We recommend booking well in advance using price comparison sites like rental cars if traveling in the peak summer season.

What to do in Chianti

Quick Facts about Chianti

  • Chianti is one of the oldest wine-producing regions in Italy
  • The wine produced in the Chianti region is primarily red and is made predominantly from Sangiovese grapes
  • Within the larger Chianti region, there’s a smaller, more prestigious area called Chianti Classico
  • Wines labeled as Chianti Classico bear the symbol of the Black Rooster (Gallo Nero), a historic emblem of the Consorzio Chianti Classico. This symbol signifies the wine’s authenticity and adherence to the region’s standards
  • The Chianti region is characterized by its beautiful landscape, rolling hills adorned with vineyards, olive groves, cypress trees, and charming villages

Greve in Chianti

Discovering Chianti begins by heading from Florence along the SS 222 road toward Greve in Chianti, an inviting town serving as a gateway to this famous region. 

The focal point of the town lies within Piazza Matteotti, boasting an unconventional triangular configuration, enveloped by arcaded walkways, stores, and taverns that offer an immersive experience into the local customs. At the heart of this square, Giovanni da Verrazzano’s statue stands tall—a tribute to the renowned explorer born in Greve, credited with discovering the bay that would become present-day New York and a significant portion of the eastern United States coastline. This legacy extends to New York City, where the iconic bridge connecting Brooklyn and Staten Island was named after him in 1964. Returning to Greve, the Castello da Verrazzano stands as the birthplace of Giovanni

Don’t miss the treasures within the Church of Santa Croce, housing significant artworks like Bicci di Lorenzo’s Madonna and Child with Saints triptych. Additionally, the Wine Museum vividly depicts the rich history of Chianti DOCG, the renowned wine long cultivated in this captivating region. Greve in Chianti stands as a captivating destination, offering a blend of cultural heritage, culinary delights, and historical significance, making it a must-visit stop in your Chianti exploration.

Good to know

Greve hosts regular events like food and wine festivals that blend music and markets throughout the year, primarily concentrated during the summer and early fall. We suggest visiting the tourist information office near the city hall on the main square to ask for an events calendar for Greve and the surrounding area.


Montefioralle - Tuscany

Montefioralle, a petite and impeccably preserved medieval hamlet nestled in the Chianti hills, boasts cobblestone streets, stone houses, and an enchanting ambiance that beckons exploration. Transporting visitors to a bygone era, it offers an authentic portrayal of medieval Tuscany. Stroll leisurely through the village, relishing Tuscan culinary delights at local eateries.

At the village’s summit rests Montefioralle Castle, regrettably inaccessible to the public; nevertheless, the castle’s exterior and the panoramic vistas from its hilltop perch warrant the ascent. The commanding views of the Chianti countryside are truly awe-inspiring. The picturesque environs of Montefioralle are ideal for unhurried walks and hikes, inviting exploration of the verdant vineyards and olive groves that define the Chianti landscape.

Depending on the timing of your visit, you might encounter local festivals and events, offering a glimpse into the lively culture and traditions of this captivating village. Montefioralle stands as a tranquil sanctuary encapsulating the spirit of Tuscany. Its medieval allure, scenic panoramas, and genuine Italian atmosphere create an irresistible draw for travelers seeking an authentic and less-traveled experience.

Radda in Chianti

Radda in Chianti, Tuscany

Radda in Chianti is a charming hillside town exuding a medieval charm that beckons exploration. Its intact city walls, narrow pathways, and delightful squares offer a pleasant experience for visitors. Explore the Museo del Chianti to delve into the rich history of Chianti’s winemaking tradition and its cultural importance. Don’t miss the chance to indulge in local wines and classic Tuscan dishes at the cozy restaurants and wine shops scattered throughout Radda.

Good to know

Ideal place to base yourself because it is close to Siena and Florence, it is the perfect area for an agriturismo experience and you can make easy day trips to Arezzo, Montepulciano and the Chianti region.


Monteriggioni is a medieval town surrounded by well-preserved walls, seemingly trapped in an era long past. Recognized for its 14 protective towers encircling the settlement, it offers an opportunity to explore unique architecture and revel in panoramic views accessible from its fortified walls. Monteriggioni’s allure is defined by its charming atmosphere and historical importance, making it a compelling stop for visitors.

Don’t miss the chance to explore the Museo Monteriggioni, situated in the town’s central square, offering insights into this enchanting town’s story. For an unforgettable experience, relish the local Tuscan cuisine at one of the intimate restaurants, fully embracing the romantic ambiance of Monteriggioni.

If you want to know more about Monteriggioni, check out our article on how to spend a day in Monteriggioni!

Good to know

If history fascinates you, consider planning your trip to coincide with the town’s yearly Medieval festival held in July.

The majority of Italians typically visit on weekends or holidays. To encounter fewer crowds, opt for weekdays or visit during the quieter hours in the middle of the day.

San gusmé

San gusmé Chianti

Just beyond the town lies the captivating San Gusmé, a quaint and timeless village offering captivating vistas. Situated in the heart of Chianti, San Gusmè remains an undiscovered treasure, providing an authentic Tuscan ambiance. Commence your day by leisurely wandering along cobblestone streets adorned with delightful shops and authentic eateries. Nearby stands the Certosa di Pontignano, a stunning monastery that hosts various events. Additionally, make sure to include Pieve Pacina in your itinerary, located less than 3 km from the town center and possibly one of the oldest churches in the vicinity.

Good to know

San Gusmè hosts a Luca Cava Festival each year on two weekends in September, offering food, crafts and wine for visitors.

San Gusmè is indeed a tiny village and the population stands approximately at 89 residents.

Gaiole in Chianti

Castello di Brolio - Tuscany

Gaiole in Chianti, tracing its roots to the Middle Ages, held significant importance as a marketplace positioned between Chianti and Valdarno, attracting various surrounding castles. Presently, Gaiole remains a pivotal hub within the region, drawing considerable tourist interest. Numerous farmhouses and wine bars in the town offer their products and warm hospitality.

In the vicinity of Gaiole, several castles and fortified sites beckon exploration, including Badia di Coltibuono, Castello di Meleto, Pieve di Spaltenna, and Castello di Brolio, now repurposed as residences for stays in Chianti and for sampling their produce.

Castello di Brolio, an imposing pentagonal fortress, boasts enchanting wall walkways and magnificent gardens, creating an evocative setting. Long held by the Ricasoli family, it serves as a prominent Chianti winery, offering wine tastings during visits.

Good to know

Brolio’s museum honors Baron Bettino Ricasoli (1809-1880), the multifaceted second prime minister of Italy, celebrated for his diverse roles as a scientist, farmer, winemaker, statesman, and entrepreneur. Dedicated to chronicling his life, the museum spans three rooms within the castle’s tower. Among his achievements, Baron Ricasoli is recognized for formulating the Chianti Classico recipe, now part of DOC regulations. Advanced booking is necessary for guided tours as no walk-ins are allowed.

Castellina in Chianti

Castellina in Chianti - Tuscany

Castellina in Chianti, a charming town with roots tracing back to the Etruscans, emerged atop a hill, commanding views of the surrounding valleys. Brimming with souvenir shops and outlets representing local wineries, its strategic location lent it significance as a key military and strategic hub positioned between Florence and Siena.

The town retains its prominence with the commanding fortress at the heart of the central square and the enchanting pathway of Via delle Volte, offering glimpses of breathtaking vistas. While wandering through the streets, visitors can marvel at magnificent noble residences once owned by influential Sienese and Florentine families.

The Church of S. Salvatore, reconstructed after World War II, merits exploration for its stunning 14th-century fresco housed within. Another noteworthy attraction is the Archaeological Museum of Chianti, which chronicles the ancient history of the region and houses numerous Etruscan artifacts, making it a compelling visit.


Volpaia - Tuscany

Volpaia, a captivating fortified village resting atop a hill in Chianti, captures the spirit of a medieval Tuscan settlement. It showcases immaculately preserved structures and meandering stone pathways that invite exploration. Explore the village’s layout in depth, making it a point to visit the Castello di Volpaia, which has been transformed into a winery. Take part in guided tours of the wine cellars and savor the exquisite wines offered for tasting. Moreover, the village hosts a delightful dining venue, La Bottega, where you can relish the flavors of local cuisine.

Panzano in Chianti

Panzano has held significance since the 12th century, playing a crucial role in defending Florence’s territories. The Castle of Panzano stood as a key defense for the Republic of Florence during conflicts with Siena, leaving remnants that still echo through the ancient town.

Traces of the castle remain evident in the ancient town, dominated today by the Church of S. Maria, dating back to 1200, but completely rebuilt in 1800 according to the neoclassical style. Taking a stroll through the historic town offers a glimpse into bygone eras, and pausing in the main square for a glass of wine is a delightful experience.

Panzano has various wine bars and restaurants where visitors can enjoy wine tastings and sample local products. Not far away lies the Pieve di San Leolino, dating back to 982.  Inside, you can find precious artworks crafted by local masters.

San Gimignano

San Gimignano - Tuscany

San Gimignano earns the nickname “Medieval Manhattan” due to its iconic towers that symbolized the wealth of noble families. This UNESCO World Heritage site is steeped in history, showcasing remarkably preserved medieval architecture that evokes a journey through time. Meandering through its intricate network of narrow streets, visitors can uncover hidden spots and explore museums such as the Museo Civico and the Collegiate Church. Don’t miss tasting the well-known Vernaccia di San Gimignano wine and the town’s famous gelato.

What to eat and where

Trattoria La Castellana, a rustic restaurant nestled in the Chianti region, atop Montefioralle’s hill near the medieval town, offers an authentic taste of Chianti cuisine in a warm family setting. Emphasizing fresh, seasonal, and high-quality ingredients, the menu features traditional recipes with a contemporary twist. Specialties include dishes with fresh truffle, appetizers showcasing local meat cuts (such as Tuscan ham, salami, and sausage), an assortment of cheeses, homemade pasta, wild boar, classic Florentine-style steak, and artisanal desserts. The cellar boasts a selection of Chianti wines from top local estates, along with renowned red wines like Brunello and Montepulciano, and a curated collection of fine wines from across Italy.

If you’re seeking an unforgettable culinary experience in Radda in Chianti, Osteria Le Panzanelle is a must-visit. Situated amid the picturesque hills, this charming osteria boasts a menu crafted with seasonal and locally-sourced ingredients. Indulge in exquisite offerings such as the flavorful pici pasta infused with truffle essence, the delightful homemade ravioli, and an array of tantalizing bruschettas. Adding to the allure, the outdoor terrace offers breathtaking vistas of the stunning Chianti countryside, enhancing your dining experience with unparalleled views. Osteria Le Panzanelle promises a delightful blend of delectable cuisine and scenic charm, making it an essential stop for discerning food enthusiasts.

For an authentic taste of Tuscan cuisine within the enchanting medieval village of Volpaia, La Bottega di Volpaia stands as a must-visit trattoria. Set in a rustic ambiance, this eatery offers a delightful array of dishes such as the hearty ribollita, flavorful homemade pasta, and the enticing Volpaia mixed grill. Complementing the cuisine, the trattoria proudly showcases a selection of local wines and village-produced olive oil, enhancing the culinary experience with genuine regional flavors. With its charming setting and delectable Tuscan fare, La Bottega di Volpaia promises a memorable dining experience immersed in the rich heritage of Volpaia’s medieval charm.

Where to Stay

Castello di Spaltenna, is a historic castle-turned-hotel that offers a luxurious and romantic getaway in the heart of Chianti. Experience the charm of a medieval castle with modern amenities. The beautiful gardens, panoramic pool, and exquisite dining make for an unforgettable stay.
Address: Via Spaltenna, 13, 53013 Gaiole in Chianti SI, Italy

Villa Bordoni is an elegant boutique hotel set in a restored 16th-century villa surrounded by vineyards and olive groves. Enjoy the tranquillity and beauty of the countryside. The hotel’s restaurant serves gourmet Tuscan cuisine, and its attentive staff ensures a memorable stay.
Address: Via S. Cresci, 31-32, 50022 Mezzuola, FI, Italy

Fattoria Montecchio offers rustic and comfortable apartments on a working vineyard and olive farm. Immerse yourself in the agrarian life of Chianti, participate in wine and olive oil tastings, and relax in a peaceful, rural setting.
Address: Str. Montecchio, 4, 50028 San Donato FI, Italy


What makes Chianti wine special?

Chianti wine, originating from Sangiovese grapes native to Tuscany, has evolved through time and regulation. In the 1800s, it was composed mostly of Sangiovese with Canaiolo, Malvasia, Trebbiano, and other grapes. Today, Chianti Classico mandates 80% Sangiovese, allowing for a blend with Merlot, Cabernet Sauvignon, or other rare varietals.

To bear the “gallo nero” (black rooster) label, a genuine Chianti must contain 12% alcohol, aged for 10 months. Stringent regulations differentiate it from Super Tuscan wines, which don’t adhere to these rules. Variants like Chianti Classico Riserva and Chianti Superiore have distinct aging requirements and alcohol content.

When should i visit Chianti?

Each Chianti season possesses its unique allure. During spring, the landscape bursts with a variety of blossoms: wisteria in April, roses in May, adorning the stone walls of farmhouses, alongside scattered lilies and poppies in the fields. Summer unveils vast sunflower fields, resonating with the symphony of crickets and cicadas. Autumn transforms the vineyards, painting them with enchanting hues of orange, red, and yellow, showcasing the splendor of fall. Meanwhile, winter casts an atmospheric spell with morning fog and chimney smoke billowing into the air.

When is the best time to visit Chianti for a wine tour?

Most people advocate for visiting Tuscany during spring or fall, citing them as the ideal times. However, here’s an insider tip: A journey to Tuscany, complete with a Chianti wine tour, remains splendid throughout the year. Every Tuscany season presents unique experiences, from the blossoming allure of spring to the celebratory grape harvest events in autumn. 

How many days do i need in Chianti?

For a brief visit, allocating 2-3 days should suffice to explore the key attractions and enjoy wine tastings at renowned wineries. This timeframe allows for visits to notable wineries, local villages, and dining experiences at authentic Italian restaurants.

However, to fully engage in the Chianti region and savor a more unhurried exploration, consider dedicating 5-7 days or even an extended period. This extended duration grants ample opportunity to delve into lesser-explored wineries, participate in cooking classes, embark on scenic hikes, and genuinely embrace the Tuscan way of life.

Are there any Tuscan dishes to try while in Chianti?

When visiting Chianti, it’s a must to savor famous Tuscan delicacies like Bistecca alla Fiorentina (T-bone steak), Pappa al Pomodoro (bread and tomato soup), Ribollita (vegetable and bread soup), flavorful Pecorino cheese, Panzanella (bread salad), and Cantucci (almond biscuits). Don’t miss pairing Cantucci with Vin Santo, a delightful sweet dessert wine, to enhance the culinary experience.

No Comments

Post A Comment