One of my favorite areas is Chianti, where the always-reliable Chianti Classico is made by family-owned wineries from some of the most beautiful vineyards.
If you’re wanting to take a trip to Chianti, and you want to see and do everything the area has to offer without paying exorbitant rates for a driver, you really should consider a self-guided wine tasting tour in Chianti.
As long as you have a designated driver, or be careful to sip and spit the wine as you’re tasting around the region, you can drive yourself to the wineries and towns mentioned in this itinerary.
This will allow you to plan your own route and spend as much or little time at each stop as you like. If you want to drink the wine, and don’t have a designated driver, you should absolutely not drive yourself.
If you’re hitting up Italy as part of a larger trip to Europe, be sure to check out our 2-week Europe Itinerary.
Planning for an Italy wine trip? Here's more
Should I Book a Wine Tour?
If not having to drive is more appealing to you, we recommend booking a group tour.
With a group tour, you don’t have to do any of the planning and someone else will drive you around the narrow, winding roads, but then you wouldn’t get to build your own itinerary and spend as much time as you want at the wineries of your choice.
However, we personally prefer to get a private driver and create our own self-guided tour of Chianti. If you work with a driver, like Giovanni Sirabella of Sunflower Tours, they can drive you around the area and you can still pick where you go and how long you spend.
How to Plan a Self-Guided Wine Tasting Tour in Chianti
You might be wondering if it’s difficult to get around, or impossible to find your way to the best small wineries tucked away in little hamlets throughout Tuscany, but it’s definitely doable, and to me it’s preferable to a packaged tour because you can stop off where ever you want, whenever you want – and believe me, you’ll want to do that often.
The wineries you’ll visited are all stunning, welcoming, and (fairly) easy to find. You will eat at the best restaurants, taste some of the best wine, and stay in the most romantic Italian hotels that just ooze Tuscan charm.
In order to do it right, we’ve created a custom-made, highly researched four-day itinerary for a self-guided wine tasting tour in Chianti.
How to Get To and Around Chianti
There are a few airports you can fly into to reach Chianti and the rest of Tuscany. The closest is Florence, however the airport is rather small and doesn’t support many international flights.
The next best option would be either Bologna or Pisa, both being about an hour and 15-minute drive from Ruffino, the northern-most winery on our list. Once you’ve arrive, you will need a car to get around Chianti.
Trust me, we’ve tried to get around using public transportation and hired cars, but it is very difficult. Trains and buses are very infrequent and private drivers are exceptionally expensive.
Yes, technically it can be done, but it’s really best to rent a car and drive yourself around. If you’re driving, you’ll just have to get good at sipping and spitting the wine.
Where to Stay in Chianti
Before we get to where to taste wine in Chianti, you should decide on a place to stay. You can reach all of the wineries from one central location, so don’t be afraid to choose one place and stay there for the full four days.
You can also hop around, if that suits you better. Chianti is actually quite a large wine region that extends from just south of Florence down to Siena (about an hour’s drive).
It encompasses many little towns, like Radda in Chianti, Greve in Chianti, and Gaiole in Chianti.
Where to stay is a big decision. There are hotels within each city, there are agritourism farms in the countryside, unique villas like The Strozzi Family Estate, and there are boutique hotels dotted throughout the area.
Here are the four options we recommend. All of them are affordable luxury and offer all the amenities you expect from this level of accommodations.
Villa Bordoni Luxury Boutique Hotel
Our itinerary is focused around the charming, upscale boutique hotel, Villa Bordoni. It’s the perfect place to stay in Tuscan countryside because it’s tucked away in the hills on a beautiful property that really makes you feel like you’ve found a secret Tuscan hideaway, but it’s still close to the places you want to go.
Villa Bordoni’s accommodations are charming Italian rustic style. It feels like staying in a nice farmhouse. It’s cozy and comfortable. Each room is uniquely laid out – no two are alike.
They have a wonderful restaurant, beautiful landscaped grounds, a pool, and a cooking school. What’s not to love?
⇒ Read reviews or book your stay at Villa Bordoni on Trip Advisor.
Another accommodation option is to stay at a winery near Greve in Chianti. The location of Fattorio Viticcio can’t be beat, because it is so close to Greve, in case you want to enjoy a dinner or a wine bar in town.
You will also have a wine tasting included in your stay. Expect to find rustic vineyard charm.
⇒ Read reviews or book your stay at Fattorio Viticcio on Trip Advisor.
Poggio Casciano at Ruffino Winery
Opening in March to guests, Ruffino Winery offers unique accommodations in their Poggio Casciano renaissance estate. It’s everything you want from a stay in Tuscany.
The views are incredible, the estate is incredibly – it feels a bit like staying with a member of the royal family. They have a pool for guests, an outdoor terrace where breakfast is served, and a sprawling estate vineyard.
Perhaps best of all, the location is perfect, just a 30-min drive from the Florence airport, and a great launching point for the rest of Chianti to the south.
⇒ Contact Ruffino Winery for information and to book a stay.
Castel Monastero Resort & Spa
Castel Monastero Resort & Spa is part of the Leading Hotels of the World group and is a luxury property. It is perfect for a relaxing stay.
The resort is set in a restored 10th century medieval hamlet and the historic castle offers beautiful views of Tuscany, a pool, a wellness center and 2 restaurants – one gourmet and one traditional Tuscan food.
4-Day Self-Guided Wine Tasting Tour in Chianti
The best way to see and experience Chianti Classico wineries in Tuscany is on a self-guided wine tour. We have personally visited each of the wineries listed on this schedule and recommend each one.
We’ve included a timed schedule that you can follow. You can, of course, omit any you don’t think you have time for, or rearrange them as you see fit.
Noon: Lunch and wine tasting at Marchesi Antinori's Rinuccio 1180
If you fly into Florence or Bologna, it’s a quick 1-hour drive down to Antinori. It’s also on the way to Villa Bordoni, where I really recommend staying.
It is located not far off the main freeway, so it’s the perfect first stop as you enter Chianti. Whereas many of the wineries in Chianti are small, family-owned operations, Antinori is just the opposite.
It is a stunning winery and well worth the visit. The grounds of the winery are huge. After you drive up to the guard gate, you’re given instructions on where to park and how to get to the winery, which includes walking up a huge spiral staircase to the top level of the building.
You’re able to book a tour and a tasting, or just a tasting if you’re pressed for time (or, like us, have heard the same story about 900 times at other wineries.
However, I think the best way to do a tasting at Antinori is to have lunch at their restaurant, Rinuccio 1180, located on top of the building with a fantastic view.
If you’re lucky, the weather is nice and you can sit at the outdoor patio, but even inside has a great ambiance and bustling energy. Pairing the wines with food is a great way to really enjoy a wine, and the restaurant makes that easy to do by providing wine flight pairings of the same wines you would try in the tasting room.
3:30pm Cooking Class at Villa Bordoni
I recommend taking a cooking class at Villa Bordoni. You can drive there right after Antinori. But don’t worry, you will cook first and won’t eat the fruit of your labor until dinner time.
We spent the afternoon learning how to make Italian favorites in the professional kitchen, instructed by one of the restaurant chefs who was very skilled and knowledgeable.
The classes vary, so check their website before you go to make sure you find one you like. There are many cooking classes in the area, but this is one of the best. Plus you can stay at the hotel, so it’s just a quick walk back to your room when the night is over.
What you cook in the class is what you’ll be eating for dinner that night in the restaurant at Villa Bordoni. It’s a small dining room, rustic and charming.
You don’t have to put together the meal yourself, which is the best part. The chefs will do the work to turn your pasta and preparations into a delicious multi-course meal.
7pm Dinner at Villa Bordoni
After an hour relaxing with a pre-dinner drink and snacking on the foccacia we’d made in the class, we were served a 4-course dinner of the dishes we had made in the class with endless bottles of wine for the table to share.
It was such a great time and one of the best things we did in Chianti.
Alternative: Dinner at Ristorante La Castellana
If you don’t wish to do the cooking class and dinner at Villa Bordoni, we recommend having dinner at La Castellana in Montefioralle.
Ristorante la Castellana is one of the best restaurants we ate at in Chianti. It’s located in the small town of Montefioralle, just a few miles from Villa Bordoni.
The dining room is very small and intimate with stone walls and floors. It truly feels like you’ve stumbled up on a Tuscan gem at this restaurant. The menu is actually quite extensive for such a small place – but not surprising, as the tables are always full!
The owner provided us with the best, most personalized service. We felt like friends instead of strangers. At the end of the meal, he brought out a bunch of bottles of limoncello and housemade grappa for us to try. It was simply fantastic.
10am Tasting and tour at Montefioralle Winery
The small town of Montefioralle is just a few minutes from Villa Bordoni, and even easier to get to is the winery by the same name. Montefioralle Winery is a small, family-owned operation, but they are one of the most welcoming we visited.
A tour of the winery takes only about five minutes and leads you through the fermentation room and the cellar, then up to the tasting room, where you’ll be seated for a private tasting.
During the nicer summer months, tastings can be done outside in their courtyard, with a fantastic view of the vines and the towering town of Montefioralle in the background.
The tasting includes generous pours of all of their current wines – Chianti Classico, Chianti Classico Reserva, IGT and a Vin Santo. As Chianti Classico is their specialty, they always have at least two years available for a vertical tasting.
We were also greeted with a plate of food to help discover how the wines pair with food. Since it was a private tasting, we were able to take as much time as we wanted to taste the wines and ask questions.
The wines were all very good and also reasonably priced. They offer an option to ship wine back to the U.S. They are open by reservation only, every day of the week from 10am to 6pm.
To book your visit and tasting: firstname.lastname@example.org.
11:15am - Wine tasting at Fattoria Viticcio
We fell into the trap of following the Google navigation to get to Fattoria Viticcio, which we were warned against prior to going. I will take a moment to warn you against it, too.
If you do follow Google, you will end up in a place far, far away from where you mean to be. Using the written direction on the website is the way to go.
Once you’ve gotten on the right road, you will snake your way up and up until you reach the wine cellar and farmhouse, surrounded by 40 hectares of organically farmed vineyards, located just 5 miles from the town of Greve.
If you’re not staying at Villa Bordoni, you should consider staying in the charming apartments at Fattoria Viticcio. Viticcio is not small, with a production of 300,000 bottles a year, but they are by no means a large winery either for Chianti.
Their first harvest was in 1964, with just 20,000 bottles, and their first entirely organic production started in 2013. Tastings are available every day by appointment only from 10am to 4pm.
The fee is €10 and includes a tasting of 4 wines – Bere (a blend of Sangiovese, Cab and Merlot), Chianti Classico, Chianti Classico Riserva, and Gran Selezione – along with salami, cheese and olive oil, also made on the property.
You can also take a tour at 11am or 3:30pm, by appointment.
1pm - Greve
Walk around the town of Greve, stopping for lunch at Enoteca Ristorante Gallo Nero in Greve. Stop for some wine tasting at Enoteca Falorni. Greve is a cute little town that’s easy to walk around and is a fun addition to the itinerary.
4pm - Wine tasting at Vignamaggio Winery
One of Tuscany’s oldest farming estates, Vignamaggio has transitioned to organic agriculture for environmental conservation, and they’ve also embarked on a vine-variety restoration project to bring back older, lesser-known varietals from the area.
There are many activities you can do at Vignamaggio, including wine tasting and tours, cooking classes, horseback riding, or enjoying lunch or dinner at the restaurant.
They offer a couple of different levels of tastings, so check out their website to decide what fits your schedule and make a reservation. They offer one of the area’s only wine-paired, multi-course dinners.
7:30pm - Dinner at Ristoro di Lamole
I was so intrigued by the ravings that I made sure it fit in our plan to eat there. We went on a Friday afternoon for lunch, after having been out wine tasting for a few hours. We had been forewarned about the drive – and I’ll make sure you are equally forewarned.
It’s not a bad drive, just really windy and long. Once you arrive at the top, you will be rewarded with one of the most amazing views.
The restaurant is very popular, so make sure you’ve made a reservation. During the high season, it would be wise to book a few weeks ahead, if not more.
They have a lovely indoor dining room with seats that face the view, and they also have a covered outdoor patio, that I assume can be opened up in nice weather.
The owner is one of the nicest people we met during our time in Tuscany. He was very helpful with the menu and even sat down with us an gave recommendations for other things to do in the area, when he learned that we were travel bloggers.
The food is outstanding. While we were deciding what to eat, we were brought a plate of cheese wedges with truffle honey to snack on. Delicious. I was excited to order the burrata, because it’s one of my favorite things to eat, and every bite was savored.
We also ordered a beef tartar and black rice risotto, both of which were fantastic. If we could have stayed and ordered the entire menu, we would have, and if it wasn’t such a long drive to get up there, we would have definitely gone back for another meal.
You’ll want to have a bit of a slower, more relaxed third day. We find that it’s difficult to keep going at full force at this point. Today, we suggest heading to Panzano to enjoy a lunch at Soloccicia, which lasts around three hours.
There are a few other wineries in the area you can go to, if you feel up to it.
11am Wine tasting at Ca di Pesa
If you’re staying at Villa Bordoni, inquire with the concierge about booking a tasting and tour at Ca di Pesa estate outside of Panzano.
They have a relationship with the winemaker, Diego Ciurletti, who has been making wine in Chianti for many years. They will be able to set you up with a tour of Ca di Pesa, which has a long and interesting history, including being rented by Antonmaria Gherardini, mother of Mona Lisa.
The house has been owned by the Auerbach family since 1998 and they’ve transformed it into a lovely home and winery, which will soon have a dedicated tasting room.
It is also available for rent in the summer months and would be a fantastic place for a family reunion.
They are committed to producing the best possible Chianti wines from their estate vineyard and continue to strive for perfection. Diego will happily tell you about the wine production and share with you the wines he has crafted.
They make a Rosato, a Chianti Classico, and Chianti Classico Riserva. We instantly fell in love with the Riserva. It is aged for 24 months in new French oak barrels, which makes it a surprisingly bold, textured wine.
1pm Lunch at Soloccicia in Panzano
You’ve probably heard about Solociccia, if you’ve done any food research on Chianti. It’s owned by famed Tuscan butcher, Dario Cecchini. For lunch and dinner every day (except holidays) they host a family-style lunch (read: party), where every dish is composed of meat.
It’s called Officina della Bistecca. If you’re a meat lover it’s an absolute must to indulge in this meat-centric lunch. The menu consists of six meat courses, seasonal vegetables, beans with extra virgin olive oil, Tuscan bread, wine, olive oil cake and grappa. All for just 30 euro.
And you’re welcome to bring your own wine – there’s no corkage fee.
Lunch is served in two seatings: 1pm and 1:30pm. Dinner is served at 8pm and 9pm. Reservations are a must (as far in advance as you can). You can book on their website.
The family-style lunch at Solociccia is a long affair, up to 3 hours. Be prepared to stay around to enjoy this fantastic meal. The plates just keep coming. And they are piled high with more food than you can imagine.
I especially love the seasoned salt they make there. It is served with the vegetables at the beginning of the meal.
Visit Fattoria La Fonti
After leaving Solociccia, it’s likely you won’t really be up for more wine tasting. If you are, check out nearby Fattoria La Fonti. You can visit the winery for a tasting from March to November, Monday to Friday, from 10am to 6pm and Saturday from 11am to 5pm without an appointment.
All other times are by appointment only. Also, if you want to tour the cellars, you need an advanced appointment.
10:30pm Tour and Wine Tasting at Castello di Radda
Located just a short drive from the town of Radda in Chianti is the winery of Castello di Radda. The estate was acquired by the Beretta family in 2003 with the purpose of expanding their wine business, which includes other wine estates in Italy.
Castello di Radda was built as a modern cellar located among the 45 hectares of vineyards, which are mostly south east and south west facing and particularly well suited for the growing of Sangiovese and Canaiolo.
These grapes are used to make their Chianti and Chianto Classico wines. A visit to the winery can include a tour of the vineyards, to illustrate the make up of the calcareous clay soil, which is fantastic for growing Sangiovese.
Once you’ve had a walk through the vineyards, you’ll better be able to understand the wines in your glass.
While at Castello di Radda, you’ll also be able to take a tour of the facilities, so you can see where the wine is made, and the systems and mechanics they use to craft such artfully produced wine.
We were lucky enough to visit during the harvest season, so were able to see the winery in action. You’ll finish your visit to Castell di Radda with a tasting of their collection of wines.
They currently have a Chianti Classico, Chianti Classico Riserva, a Chianti Classico Gran Selezione called Vigna Il Corno, and a Super Tuscan called Guss, named for the Gussali Beretta family.
All of the wines are well paired with local Tuscan foods. We particularly loved the Guss paired with lamb chops.
A reservation is needed in advance to see and experience the vineyards. They are open from Monday to Friday from 10:30am to 5:30pm. From April 28 to October 13, they are also open on Saturdays.
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12:30 Lunch at Principe Corsini's Osteria Le Corti Restaurant
From both a historical and viticultural perspective, a visit to Principe Corsini is an absolute must.
You’ll have a chance to tour the winery, but first we recommend stopping in at Osteria Le Corti for a lunch of traditional Tuscan dishes, served in the ancient wine cellar, overlooking the barrel room.
Not only does it offer this unique and fascinating atmosphere, the food is prepared with seasonal, fresh ingredients that showcase the best of the area’s cuisine, served with perfectly paired Principe Corsini wines.
Osteria Le Corti is open for lunch every day. Dinner is by reservation only.
For reservations and information: Phone: +39 055 829 3026 Email:email@example.com
1:30pm Winery tour and tasting at Principe Corsini
To envision Tuscany as it was in the 14th century, one has only to visit Principe Corsini. The estate was purchased in 1363 by the Corsini family for the production of wine and olive oil.
In the 16th century, owner Bartolomeo Corsini and his brother Filippo commissioned the construction of Villa Le Corti, which adequately reflected the family’s status in the community.
The vast underground cellars were built in the early 1600s to manage the production of wine and olive oil from the surrounding sharecroppers, which required great organization and space.
The original design is still useful for the current facilities, and everything has been kept original.
Visitors can visit the villa and the historic wine cellar on a guided tour. The villa is a true sight to see. Having been restored by the current owners, Clotilde and Duccio Corsini, the villa displays architecture from the late Renaissance at its fully historical glory.
You’ll see ancient crests, inscriptions, Roman busts and period artifacts as you pass through the impressive courtyard inside the villa.
Following a tour of the villa, you’ll have a chance to walk through the production areas for both wine and olive oil, and into the cellar where the wine, and even some grapes being dried for Vin Santo, sleep peacefully.
If you didn’t already try the wines during your lunch at Osteria Le Corti, you’ll finally have a chance to try the many wines in the Principe Corsini collection, including the Le Corti Chianti Classico DOCG, the Cortevecchio Chianti Classico DOCG Riserva, the Zac IGT Sangiovese (which was our favorite), and the Don Tommaso Chianti Classico DOCG.
The lineup of wine by Principe Corsini doesn’t end there. You can choose to taste a number of others, but we think these reflect the heart of the winery. Enoteca Le Corti is open on Sunday and Monday 10am-3pm, Tuesday 10am-5pm, and from Wednesday to Saturday 10am-6pm.
Phone: +39 055 8293026
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3:30pm Winery tour and tasting at Ruffino Winery
Ruffino Winery has more than 140 years of history. It was founded in 1877 by cousins Ilario and Leopoldo Ruffino, who wanted to try their hand at winemaking.
Their wines soon became well known in the region and internationally, winning them a gold medal for their Chianti in the 1881 Milan Wine Exhibition.
Ever since then, they’ve been making exceptional wines, even becoming the official wine supplier to the Italian royal family. This is one winery in Chianti you don’t want to miss.
In fact, if you have time to spend, we highly recommend staying at Ruffino for a couple of days to soak up the beautiful surroundings and enjoy the offerings of the winery.
As we mentioned in the “where to stay” section, Ruffino’s accommodations will open in March 2019 and with it comes an extraordinary estate experience, complete with a pool to lounge around, a terrace with spectacular views, and the opportunity to stay in for a decadent lunch.
If you only have a few hours to spend at Ruffino, be sure to book one of their tour and tasting experiences that start with a 1 hour 15 min tasting of the Ruffino classics, to a 2-hour vertical wine tasting of their most iconic wine, the Riserva Ducale Oro.
During each, you’ll have the opportunity to see the cellars and walk around the property to take in the sweeping vineyard views.
The wines you’ll definitely want to try at Ruffino are the Chianti Superiore (which is now being bottled in the classic Chianti bottle we so love), the Riserve Ducale Oro Gran Selezione DOCG, the Modus 93-point rated Toscana IGT, and the newly released, limited edition Romitorio di Santedame Chianti Classico Gran Selezione.
If you can spare the time, we highly recommend speaking with Ruffino about setting up a wine tasting lunch while you’re there. There’s no better way to experience and taste the wines, as they pair so well with the local cuisine.
Ruffino is open from Monday to Friday from 9am to 6pm for prearranged tours and tastings. Be sure to make an appointment in advance.
Phone: +39 055 64 99 712 | Email:firstname.lastname@example.org
After experiencing Ruffino Winery, you are within close proximity to Florence.
From here you can go into the city or very easily reach the airport to fly home.
Chianti Infographic – Please share on Pinterest!
We know you will love Chianti as much as we did. There are so many more wineries and restaurants besides the ones mentioned that you can visit. If you have a week or longer to spend, we highly recommend staying longer at each to truly discover all they have to offer.
The hospitality in Chianti is incredible. Do stop back in to tell us what your favorite winery experience in Chianti is! We want to hear from you.
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