Chianti Wine Road Itinerary in Tuscany for Wine Enthusiasts

What is Strada del Vino del Chianti or Chiantigiana?

Welcome, Wine Enthusiasts! In this article, we’ll take an exciting journey along Italy’s world-famous Chianti Road—Via del Chianti. Picture yourself surrounded by rolling vineyards, visiting quaint stone villages glimmering in the sun: THIS is the true essence of Tuscany. This is where the magic happens. You’ll explore Chianti’s finest and, perhaps, even learn a secret or two about the art of winemaking. Get ready to uncork the magic of Chianti, losing yourself in a unique world of medieval towns, world-class wines, and breathtaking landscapes!

As I outlined in the “How to Explore Tuscany in 1 Week” article, the Chianti Wine Road (also known as “Chiantigiana”) stretches between Florence and Siena, passing through picturesque towns such as Grassina, Impruneta, Panzano, Greve in Chianti, and Radda in Chianti. Each town adds the suffix “in Chianti” to emphasize its strong connection to this land and add a distinct character.

This itinerary will make everybody happy, from wine enthusiasts to history buffs, and nature fans alike. An amazing experience that will create unforgettable memories.

Follow This Chianti Wine Itinerary

Start an extraordinary adventure through Tuscany by following the winding SR222 Chianti Wine Road from Florence. This scenic drive will lead you on a fascinating discovery of the Chianti region’s charming landscapes, historical villages, and world-famous vineyards—not forgetting, of course, the finest wines produced here and the rich cultural and culinary heritage that awaits!

Discover Grassina: Day 1 on the Chianti Wine Road

This Chianti wine road itinerary assumes you are departing from Florence.

Grassina: The Village of Washerwomen

Morning: Begin your “wineventure” in Florence by picking up your rental car and setting off towards Grassina.

Once a bustling hub for local washerwomen, whose rhythmic pounding of clothes echoed through the narrow streets, the village has kept an authentic charm that transports visitors to a simpler time.

Grassina’s Attractions

Chiesa di San Martino a Strada (Church of San Martin) is a historic church with a single nave and a pitched roof. Inside, you will find a painting attributed to the school of Verrocchio—depicting the Virgin and several saints. If the name Andrea del Verrocchio sounds familiar, it’s because he was a famous sculptor and painter master —and yes, Leonardo da Vinci’s teacher. Imagine the creative energy that flowed within those studio walls!

Outside, a frescoed tabernacle by Pietro Annigoni graces the corner with Via Chiantigiana.

Monumento alla Lavandaia (Laundress Monument), in Piazza Umberto I is a life-sized bronze statue symbolizing the town. It depicts a laundress washing clothes, adorned with small animals on her dress.

Fonte della Fata Morgana (Fata Morgana Fountain): Bernardo Vecchietti commissioned this unique garden architectural jewel between 1573 and 1574. Inside is a fountain featuring a marble statue of Fata Morgana (Morgan the Fairy) created by Giambologna.

Events in Grassina

On Good Friday, Grassina comes alive with a sacred tradition—the Historical Reenactment of the Passion of Christ. Since 1634, over 400 costumed figures traverse the town center in a solemn Historical Procession, joined by another 80 characters who bring to life 14 scenes depicting the life of Christ, culminating in the Crucifixion.

Where to Stay in Grassina

Villa Grassina

In the hills near Florence, you will find this characteristic Tuscan Baroque villa nestled in the tranquility of the charming countryside at the gateway to the Casentino Forests National Park, along the roads of Chianti Rufina. The villa, with its elegant facade, underwent a complete renovation, restoring not only its function as a farm but also as a vacation retreat. Surrounded by woods, meadows, and olive groves, Villa Grassina is an agritourism establishment that respects tradition.

• Location: Via di Grassina 5, Pelago, Tuscany, Italy.
• Overview: Villa Grassina is a charming estate surrounded by vineyards and olive groves. It offers rustic-style apartments with modern amenities, making it an ideal base for exploring the Tuscan countryside.
• Accommodations: The apartments feature exposed wooden beams, terracotta floors, and cozy fireplaces. Each unit has a fully equipped kitchenette, allowing guests to prepare their own meals.
• Amenities:
  • Swimming pool with panoramic views
  • Tennis court
  • Outdoor dining areas
  • Barbecue facilities
• Proximity to Attractions:
  • 20 km from Florence
  • Close to the Chianti wine region
• Traveler Reviews:
  • Villa Grassina receives positive reviews for its tranquil setting and authentic Tuscan experience.
  • Guests appreciate the friendly staff and the opportunity to explore nearby vineyards and historic towns.
  • Some visitors recommend renting a

Chianti Wine Road – Day 1: Afternoon

Impruneta

Afternoon: Continue to Impruneta, renowned for its centuries-old tradition of terracotta production. Admire the town’s architectural beauty and perhaps even find a unique Tuscan memento. Nearby, Strada in Chianti, a charming hamlet, draws you in with its peaceful atmosphere. Explore the historic St. Christopher Church and soak in the stunning views.

Overnight: Settle in for the night at the charming Villa Il Leccio in Strada. This 18th-century villa, nestled amidst vineyards and olive groves, offers authentic Tuscan hospitality with its elegant accommodations and exquisite local produce.

Explore Greve and Panzano: Day 2 on the Chianti Wine Road

Greve in Chianti

Morning: Get into the heart of Chianti, starting with Greve in Chianti, the true capital of the Chianti wine road. Discover the secrets of Chianti Classico at any of the engaging museums, and seize the vibrant atmosphere of Piazza Matteotti, a triangular square lined with artisan shops and restaurants.

Greve’s excellence extends beyond wine, including delicious cured meats and handcrafted iron and wood products, all showcased in the charming market square, which comes alive with outdoor fairs on weekends.

What to See in Greve

Greve’s triangular-shaped square, Piazza Matteotti, serves as the town’s main point of reference. Despite not being a perfect square, it remains the focal point of Greve. What sets this place apart, aside from its unusual shape, is the portico that wraps around three sides of the square. This portico continues to house boutique shops, artisan workshops, and delightful restaurants. The beauty of Greve lies in its compact size—you can easily explore the entire town on foot. And right in the heart of the square, near the city hall, stands a large statue of Giovanni da Verrazzano. If you are from New York/New Jersey this name will sound very familiar…. Yep, we are talking about the renowned explorer who discovered the Hudson Bay in New York and was born just a few kilometers north of Greve. Perhaps you noticed Castello da Verrazzano along the Chiantigiana before reaching Greve?

Greve is also famous for some butcher shops and meat specialties. For example, the renowned Antica Macelleria Falorni is a must-visit butcher shop. But also the Antica Macelleria Cecchini in Panzano in Chianti is renowned worldwide. Led by the legendary butcher Dario Cecchini, this establishment is a must-visit.

Greve’s Events

Greve hosts several annual events. The Flower Festival typically takes place around May 1st, and the town also celebrates the feast of the Holy Cross, its patron saint, with festivities throughout the year.

Panzano in Chianti

Afternoon: Head to Panzano in the afternoon, and immerse yourself in the idyllic charm of Panzano in Chianti, an idyllic holiday resort at 498 meters above sea level.

History meets charm in Panzano! Explore the 19th-century Santa Maria church, built on a medieval base. Take a photo on its stunning stone staircase and imagine the castle that once stood there (a remnant of the tower is still inside!). Wander the quiet, cobbled streets, feeling like you’ve stepped back in time. Follow the main road connecting the town’s two halves, browsing charming shops and artisan workshops filled with local treasures.

Two Sides of the Coin: Panzano offers two entrances, each revealing a different side. Arriving from Florence or Greve in Chianti, you’ll first encounter the lively Gastone Bucciarelli square, bustling with shops and restaurants. The historic center lies just beyond, waiting to be discovered.

Where to Stay in Panzano

Villa Il Palagio

• Location: Via Il Palagio 59, Pian dell’Isola, Rignano sull’Arno, Tuscany, Italy.
• Overview: Villa Il Palagio is an elegant villa surrounded by a large private garden. It offers air-conditioned accommodations with flat-screen TVs and fully fitted kitchenettes. Florence is approximately 30 km away.
• Accommodations: The suites and apartments come with free Wi-Fi, a seating area with a sofa, fine parquet floors, and neutral color tones that create an elegant ambiance. Some units even offer balconies or valley views.
• Amenities:
  • Swimming pool
  • Rooftop terrace with panoramic views of the Tuscan countryside
  • Games room with a billiard table
  • Laundry facilities
• Proximity to Attractions:
  • 3 km from The Mall outlet shopping center
  • 15 km from the Chianti wine area
• Traveler Reviews:
  • Overall, Villa Il Palagio receives a very good rating based on 162 reviews.
  • Positive aspects include the great location in the Tuscan countryside and spacious villas.
    

Chianti Wine Road – Day 3: Radda in Chianti

Radda in Chianti

On day 3 of the Chianti wine tour itinerary, you will head back on the road towards Radda in Chianti. This lovely town exudes timeless beauty as you admire it from its hilltop location, nestled between the Arbia and Pesa rivers and covered by an intricate web of vineyards.

Radda is synonymous with vineyards. Situated at the center of Tuscany’s Chianti region – dubbed by English expats “Chiantishire”—its location offers spectacular vistas in every direction. Built during the 15th century and later rebuilt after Spanish troops destroyed it, its Palazzo del Podesta’ stands as one of Radda town walls primary landmarks with ceramic coats of arms from noble Radda families adorning its honey-colored facade while Church San Niccolo houses an iconic 15th-century “Madonna and Child,” which came straight from Radda Castle chapel!

Recommended Attractions in Radda

Piazza Ferrucci is at the core of Radda, where the remnants of its original castle dominate this iconic square. From here, you can enjoy unparalleled panoramic views reminiscent of medieval Europe.

Apart from being home to the headquarters of the Chianti Consortium (founded in 1924 and Italy’s oldest, symbolized by a black rooster), this little village boasts a splendid medieval center that invites exploration on foot. Not far from Radda lies Gaiole, once an important commercial hub in the past and now a paradise for wine enthusiasts and agriturismo lovers. In the vicinity, you’ll find several fortified dwellings, such as the Pieve di Spaltenna, which houses a precious wooden crucifix dating back to the 1400s, and Castello di Brolio, the Ricasoli family’s residence since the 12th century and still producing excellent Chianti Classico today.

 Radda: Where Vines Rule Supreme 

Radda’s terrain provides ideal conditions for cultivating vines and olive trees, with wine being the mainstay source of income for the local population. Radda’s winemaking traditions have a deep history, and the international community has celebrated the long-standing recognition of Radda wines. Grand Duke Cosimo III officially recognized and established Chianti district boundaries through his Chianti Classico law enacted 300 years ago, marking it as the world’s first legal wine production area. This year marks this anniversary.

Where to Stay in Radda

Relais Vignale & Spa

• Location: Via Pianigiani 9, Radda in Chianti, 53017, Tuscany, Italy.
• Overview: Relais Vignale is a charming historic villa nestled in the Chianti Classico area. Its panoramic views across the Tuscan countryside and vineyards create an enchanting backdrop. The villa, renovated according to its original architecture, offers the standards of a 4-star hotel.
• Accommodations: The elegant rooms feature individual designs, air conditioning, heating, and satellite TV. Some suites boast balconies or terraces with views of the surrounding hills. Antique furniture, frescoed ceilings, and grand fireplaces add to the villa’s allure.
• Dining Experience:
  • Vignale Restaurant: Savor traditional Tuscan dishes and fine local wines. The menu includes grilled meats, cold cuts, cheeses, and aromatic pasta dishes. In summer, dine on the magnificent panoramic terrace; in winter, enjoy the heated terrace veranda or the warm and welcoming rooms in the “Taverna.”
  • Wine Tastings: Attentive staff organize tastings in the property’s wine shop.
• Amenities:
  • Outdoor heated pool surrounded by a floral garden
  • TV room, lounge bar, and library
  • Free Wi-Fi in communal areas
• Exploration:
  • Explore the nearby villages of the Chianti Classico wine region.
  • Both Siena and Florence are under an hour’s drive away.
    

Palazzo Leopoldo Dimora Storica & Spa

• Location: Via Roma 33, Radda In Chianti, 53017, Tuscany, Italy.
• Overview: Palazzo Leopoldo is a blend of history and elegance. It comprises a patrician villa dating back to 1310 and an adjacent historical building. Nestled in the medieval center of Radda, surrounded by the Chianti countryside, it offers a captivating stay.
• Accommodations: The ancient manor offers uniquely decorated large rooms for accommodations. Junior suites and spacious suites feature original fireplaces and frescoes. Each room includes a 32-inch LCD TV and complimentary mineral water.
• Wellness and Fitness Area: Guests can indulge in massages, sauna, Turkish bath, and relax on the sun terrace. The heated indoor swimming pool with a hydromassage area is a delightful retreat. Additionally, there are two outdoor hot tubs and a private spa area available upon request.
• Dining Experience:
  • La Perla Del Palazzo: The hotel’s fine restaurant serves delectable Tuscan cuisine. Dine amidst lush gardens or on the beautiful terrace overlooking the Chianti hills.
  • Cooking Courses: Guests can participate in cooking courses held in the historic kitchen of the building.
  • Wine Tastings: Explore the flavors of the region in the property’s wine shop.
• Local Attractions:
  • Chianti Cashmere Goat Farm: Approximately 0.9 miles away.
  • Podere L’Aja: Just 0.3 miles from the villa.
  • Palazzo Del Podesta: A historic landmark right at your doorstep.

Transportation

One of the best ways to enjoy a Chianti wine tour is by either renting a car or hiring a car service company, that can offer comfortable and reliable transportation, professional yet friendly drivers, a tailored itinerary designed around your preferences and budget, plus all necessary reservations, entrance fees and logistics handled for you, leaving you free to have fun while they take care of everything for you!

Many car service companies offer Chianti wine tours from Florence or other locations in Tuscany. Check my page on transportation for info on rental cars and car service with drivers.

Conclusion

If you’ve always wanted to explore wineries in Tuscany while enjoying breathtaking scenery, rich history, and delicious cuisine, la Strada del Chianti is perfect for you. Download the free Chianti Wine Road Itinerary here. Here are some guided tours you may be interested in: CHIANTI TOURS.

If you are interested in a list of accommodations and best eateries, write a comment below.

For a list of recommended wine tour operators, click here.