Chianti Itinerary: Visit for 5 Days of Exploration

By | Wine & Travel Writer, Consultant & Marketer
Last Updated: August 31, 2023
Beautiful aerial view when visiting Chianti on a 5 day trip

Tuscany is one of Italy’s most well-known and highly regarded wine regions, particularly to those of us outside of Italy. We’ve all seen the images of the rolling hills covered with vineyards and olive groves, winding roads lined with cypress trees and the hilltop castles dotting the landscape. Tuscany is very much the dreamscape you imagine, but at 9,000 square miles it can be daunting to know where exactly to start. So, whether you’ve never been, or have been but are looking to explore more, let’s take a little journey to central Tuscany, the region of Chianti

Chianti comprises roughly 40,000 vineyard acres of Tuscany, but we’re going to zone in on one small area for a five-day itinerary that will allow for relaxation, vineyard exploration, cultural and historical excursions and of course, food and wine. While 5 days is typically sufficient for visiting Chianti, you can certainly extend this trip to travel at a more leisurely pace, which we highly recommend and is in line with the classic Italian lifestyle.

We can get super technical and go into the differences of Chianti and Chianti Classico, or the grapes used in the wines, and we do that here, but for purposes of this piece, we’re going to dive right in and explore. Who’s ready to join us?

How To Visit Chianti

The easiest way to travel to Chianti is via Pisa International Airport. You can find some great flight deals here. For this itinerary, we recommend renting a car at the airport, from which it’s a short 1.5-hour drive to Querceto di Castellina, the suggested accommodation.

Likewise, if you have a flight that will take you into Florence, the drive to Querceto di Castellina is only one hour, plus it will give you an option to spend a night or two in Florence on the way out. Alternatively, flights into Rome are often more direct, and it’s only a three-hour drive north from the eternal city, which makes for a great place to start or end your trip for a day or two.

RELATED: These Are the Best Wine Tours to Book from Florence

Winetraveler Pro Tip: While visiting or staying in Florence, we highly recommend taking the highest-rated guided cheese, wine and lunch day tour with Walkabout. This will get you off-the-beaten-path and ensure you don’t have to worry about the logistics of driving around yourself. You’ll see a ton, try both the food and wine with an immersive guide and have a deeper experience in Chianti. If you’d prefer a private guided experience from Florence to avoid groups, this day trip is perfect for couples. Another fun way to explore the region is on a guided bike tour!

Where To Stay in Chianti |
Un-wined at this relaxing accommodation in Castellina, Chianti, Tuscany at Querceto di Castellina. Image courtesy CloudJam.

Where To Stay in Chianti

As for where to stay, you can find many options from hotels and B&Bs to private rentals, but for this itinerary, I’m suggesting the agriturismo at Querceto di Castellina. Quite simply, this family-operated, organic vineyard estate on 130 acres, is centrally located, offers an authentic Chianti Classico experience, and will have you feeling relaxed the moment you step foot on the stunning property.

Owned and operated by the Di Battista family, Querceto di Castellina offers nine fully-equipped vacation apartments and one guest suite with the main structure dating back to the 1400s. Although historic, each apartment is private, modernized, comfortably furnished, and features a full kitchen. The Livia Suite, the only accommodation without a kitchen, offers breakfast daily.

Guests at Querceto will be welcomed by a member of the family and treated to a complimentary wine tasting of one of the winery’s organic wines. The agriturismo also offers a pool, expansive views from the terrace and private outdoor spaces dedicated to each accommodation. Family matriarch, Laura Di Battista, also runs an onsite Tuscan cooking school where guests can enjoy cooking lessons or a light lunch.

Winetraveler Tip: Querceto di Castellina is also a highly sought-after wedding destination. Jacopo Di Battista, along with his American wife Mary, directs the wine and hospitality for the winery, with Mary offering complete wedding planning for couples interested in a vineyard wedding.

5 Day Itinerary For Visiting Chianti Tuscany

Day 1 – Querceto di Castellina

Whether you’re arriving directly from your international flight, or after a few days in another European destination, for the first day in Chianti we recommend making use of your complimentary portfolio wine tasting at Querceto di Castellina. You can also lounge poolside or perhaps wander through the expansive estate vineyards, all while breathing in your Italian surroundings. It’s the perfect way to relax and immerse in the Tuscan lifestyle.

Founded by Laura Di Battista’s father, Giudo Masini in 1945, Querceto di Castellina was intended as a countryside retreat for his family; however, his daughter Laura and her oldest son Jacopo had other intentions. In 1988, Laura began renovating the property’s cottages into an agriturismo and improving the vineyards.

In 1998, Jacopo continued his mother’s improvement of the vineyards and produced the winery’s first vintage. The vineyards have been sustainable since 1998 and organic since 2012. While mostly comprised of Sangiovese vines, guests will also find Merlot, and two white grapes – Roussanne and Viognier. Querceto is the only winery in the Chianti Classico producing a white wine with this particular blend of grapes (along with traditional Chianti Classico and IGT wines).

Depending on your desires and the time you arrive, additional tasting options are available at Querceto, including a wine and artisanal cheese pairing, a winery tour combined with a portfolio tasting, and a unique vertical tasting of various vintages of Querceto di Castellina wines to demonstrate how they change over time.

For those with parties of six or more, the agriturismo offers one of the most intimate and personalized experiences, dinner in the vineyard. The menu is chosen with you prior to your visit, and after an aperitivo on the winery terrace, you’ll be escorted to the Livia vineyard for a four-course candlelight dining experience prepared by Chef Laura. The meal will close with a coffee service at your choice of location: the vineyard, tasting room or covered terrace.

If you’re traveling with a smaller group or are looking for an alternate dining option, on this first evening in Chianti I suggest a short 10-minute drive to Dario Cecchini, a butcher shop and kitchen run by renowned butcher and chef, Dario Cecchini. Some of you may remember it from his episode on Netflix’s Chef’s Table. Being a butcher, you can expect plenty of meat options at each of his three restaurants, Officina della Bistecca, Solociccia, and Dario DOC; however, vegetarian options are also available. Seatings range from 10 to 50 euros per person depending on the restaurant and are served with a house wine. Guests are also invited to bring their own wine (there is no corkage fee).

On Day 2 of your Chianti trip, expect to spend a day in medieval Pienza.

Day 2 – Pienza, Italy

After the exquisite dinner of night one, it’s time to get your legs moving for today’s active day trip. Drive 1.5-hours to Pienza and leisurely roam the ancient city’s streets, browse the numerous porcelain shops, or if you’re so inclined enjoy some orange and fennel gelato (or any number of other flavors) at Buon Gusto Gelateria. Plan to spend two hours wandering this historic Tuscan city before heading for lunch at Podere il Casale.

Within a brief 10-minute drive, you’ll arrive on a ridge in the Sienese hills at Podere il Casale, where you can look back for a breathtaking view of Pienza. An organic farm, the structures at Podere il Casale date back more than 300 years. Here you’ll find stables, farm animals, hives for honey production, olive groves, gardens and a scenic wooded area. This self-sufficient farm offers a lunch featuring products grown on the farm or sourced from organic neighbors. Reservations are recommended (and special diets can be accommodated in advance) for the dining room situated in an old restored barn with a large fireplace, or outside in either the farmyard or on the beautiful terrace which overlooks the Val d’Orcia, Pienza and Monte Amiata.

Winetraveler Tip: You can also purchase items to takeaway for later, and with the full kitchens at Querceto, it’s a great option for a light meal at sunset back at your vacation apartment. In addition to wines, cold-pressed extra virgin olive oil, pasta and honey, raw milk sheep or goat cheeses are also available.

If time allows, Podere il Casale offers several experiences at the farm from truffle hunting to farm tours, or cheese-making demonstrations. However, if you prefer more walking and exploration, drive back an hour toward Querceto to Siena.

Siena is one of the quintessential Tuscan cities and worth an evening of exploration. Take a guided walking food and wine tour in Siena, Drink on the Piazza del Campo, or dine in one of the narrow, cobblestone streets of the historic center before returning to your apartment for the night. (Note: You’ll have to leave your car outside of the city center as cars are not allowed.)

Chianti Itinerary: How To Spend 5 Days in Chianti, Tuscany • Winetraveler
A taste of what you can expect at sunset while relaxing among the vines in Castellina at the heart of Chianti Classico.

Day 3 – Chianti Classico

Perhaps you’re inclined to lounge about the grounds of Querceto today, or maybe a few winery visits would be of interest. If spending the day poolside with a good book, followed by a light lunch prepared by Chef Laura is your idea of perfection on this Tuscan morning, by all means, indulge yourself and pick back up with the itinerary at Monte Bernardi for an afternoon wine tasting.

However, if you’re craving more wines and vines, after a breakfast on the winery terrace drive 25 minutes to Villa Calcinaia in Greve. Villa Calcinaia has been in operation since 1524 and today is operated by the 20th generation of the Capponi family, an important noble family from Florence. In fact, if you’re lucky, Count Sebastiano may even host your tour and tasting! Reservations must be made in advance and can include a tour and tasting or a tour, tasting and light snack.

From here, head back toward Querceto, and make another easy winery stop at Monte Bernardi. The estate name — Monte Bernardi — originated in 1085 but the first estate wines weren’t produced until 1992, as most of the grapes were sold to neighboring wineries. The tasting room for this small production winery is open from April to October by appointment only with visits including options of a tour and tasting or tasting only.

As for dinner this evening, I recommend the Osteria Le Panzanella, a short 10-minute drive from either Monte Bernardi or Querceto. It’s a classic Tuscan Osteria with a wine list that is sure to please any wine lover.

Day 4 – Kidding Around

Much like the previous day, you can opt to lounge about Querceto for the morning, or start your day with a 35-minute drive to Riecine. Originally owned by a monastery until the 20th century with church archives from 1112 A.D. providing the earliest known record of the vineyards by the same name, Riecine offers tastings Monday through Friday in the newly appointed tasting room. The winery is closed in December and open to tastings on Sundays by appointment only.

As for today’s lunch and adventure, I suggest the unique experience found at Chianti Cashmere. Chianti Cashmere is a working goat cashmere farm, and by reserving ahead of time, you can visit the farm, interact with the goats and learn how cashmere is produced. This unique experience is then followed by a simple, leisurely lunch in the kitchen’s little garden. Local cheeses from area sheep and goat farms, wine from the neighboring organic vineyard, and fruits and veggies from the local farmers’ market are all served. Beginning at 4 p.m., you can visit the cashmere shop for yarn, handwoven scarves, shawls, throws and even cashmere goat’s milk soaps.

Winetraveler Tip: If you’re spending more time in the region and are so inclined, depending on the season, Chianti Cashmere also offers sheering and shepherding experiences!

Finally, if time permits, or if you opted to lounge at Querceto for the morning, it’s easy to squeak in a visit at nearby Il Molino di Grace, which sits on more than 70 acres of vineyards that have been producing traditional Chianti Classico wines for over 350 years. In addition to classic wines expressive of the region, Il Molino is within 10 minutes of Querceto and accepts walk-ins for tasting. Tours are also available by appointment.

Day 5 – Tuscan Food

For the final day of this itinerary, we suggest booking a cooking class with Chef Laura at Querceto. Your class will begin in the morning with a visit to the local market and butcher to select the perfect ingredients and is followed by an expert tutorial from the master herself. Classes are as hands-on as you want to get – join Laura in preparing the four-course meal or sit back with a glass of Querceto wine and watch how it’s done. The class culminates with lunch on the terrace which can be enjoyed with wine pairings or a bottle of their L’aura Chianti Classico. It’s the ultimate way to experience the Tuscan lifestyle on your last day in Chianti.

Alternatively, spend the morning relaxing and head into Castellina for the afternoon. Here we recommend a visit to Bibbiano, a winery and olive oil producer since 1865. By making an appointment in advance, you can select your wine experience ranging from a tasting in the vineyards overlooking the Val d’Elsa, to a tasting of historical vintages, or a food and wine pairing prepared by the house. And of course, this being your last evening, we also recommend an exquisite dinner at Ristorante Albergacccio di Castellina. Here you’ll be treated to creativity and quality, new tastes and flavors and fine-dining presentations within a family atmosphere. It’s a great way to end your stay and reflect on the experience over a final bottle of Chianti Classico.

Plan Your Getaway

As always, the Chianti itinerary suggested above can be done as a whole, or in parts, depending on the amount of time you have and the pace at which you want to move. No matter how you choose to spend your time in this quintessential Tuscan region, it’s sure to seep into your soul and create memories to last a lifetime. Buon viaggio!

Frequently Asked Questions about Visiting Chianti

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