Travel Guide: Chianti

Jun 16, 2023by Madi Lowry

by Madison Lowry

Last summer we completed a month-long trip through France and Italy in the Chianti Classico region of Tuscany. While wine was the main attraction, we had the most beautiful week under the Tuscan sun and cannot recommend a trip here enough! If you decide to make the trip, here are some of our tips and favorite spots we visited. 

How to get there:

Start your journey in Florence (Firenze - pictured below). From here, you can either rent a car to drive to your destination or take a city bus. We took the bus from Firenze to Greve in Chianti and then rented a Vespa to take us to our accommodations!


**Take the bus from the SITA Bus station next to the Santa Maria Novella train station. Let a train station employee (working behind the glass) know where you are headed, and they will help you get on the right bus. We often find it helpful due to the language barrier, to put our destination in Apple/Google Maps, select the public transit option, and show this to the train station employee.**

Although we had a blast driving the Vespa all around the countryside, we would recommend renting a car to beat the summer heat with AC, enjoy a more comfortable ride, and feel a little safer. (The good news is that they still drive on the right side of the road in Italy.) However, if you are on the adventurous side (and want to save a little money on gas), definitely get a Vespa! Is there a more quintessential Tuscan experience than this?!

We found Greve in Chianti to be very central to all the wineries and other cities that we wanted to visit. But to get as far as Sienna, which is the southern termination of Chianti Classico, you will have to drive for about an hour. Our longest ride was an hour and a half to Montalcino - one way…but luckily this is some of the most pristine driving on Earth!

Where to stay:

We stayed in a town called Lucolena, which is a 17-minute drive from Greve in Chianti. The short drive was always a blast on our Vespa and was more than worth it to spend time out of the city and in the wine country. Main places to stay:

  • Airbnbs: Always a great option for unique stays if you are planning to stay in the city centers. Not our first choice, but still great and inexpensive finds.
  • Agriturismos: This is a ‘farm stay’ or style of vacationing in farmhouse resorts. The bookings will range from individual rooms to entire houses for larger groups or families. We opted for one of these and stayed at Fattoria L’Ottavo in Lucolena. Most can be found by searching ‘Algriturismo’ on and exploring via the map. All of these places are farms, so will likely produce their own wine and/or olive oil, and might have some chickens and goats hanging around! At ours, we had our own apartment, wifi, breakfast, access to a pool, and the option to taste wine and olive oil. The employees also helped us book dinner reservations each night at local restaurants that were way better than we could have found on our own. **Sadly, do not expect A/C, but you can set A/C as a filter on — these resorts are expensive.** Side note: you won't reeeeallly need A/C. Even in the hottest part of summer, Chianti enjoys really cool nights due to a cooling breeze brought in by the coast. And during the day you should be drinking wine by the pool or in nice A/C at the tasting rooms.


  • Hotel: The nicest option of all! There are many 5-star hotels in the wine country, often attached to reputable wineries. Our top recommendation, and on our wish list, for a hotel stay is at San Felice. This hotel, actually an old village surrounded by vineyards, has an on-site Michelin star restaurant, gorgeous pool, tennis courts, gym, chapel, spa, heliport, tesla chargers, e-bikes, and of course REALLY delicious wine (they sell internationally).


Where to eat: 

As mentioned in the “Where to stay” section, we recommend asking your host or concierge for local recommendations and assistance with booking reservations. Of course, they will be able to recommend restaurants that are close by and way better than Google will provide, but they will also be able to assist with reservations when the language barrier may get in the way. Places we ate and recommend:

  • Officina Della Bistecca: This world-famous steak restaurant was featured on the Netflix show, Chef’s Table. **See the famous chef Dario talking to guests in the photo below** Be sure to make reservations ahead of time!! This place is a must. I will leave out details so it can remain a mystery, but I will say be prepared to eat A LOT of meat. 


  • Ristorante Pizzeria La Cantina - This restaurant is located in the town of Greve. We recommend getting reservations as this was one of the most packed spots in this small town.
  • La Castellana - Located in Montefioralle, a small village above Greve. A large majority of dishes featured truffle! We sat on the patio (across the street from the small restaurant) and had the most stunning view of the countryside.
  • Osteria il Rifugio del Chianti - This was recommended by the concierge at our agriturismo and was arguably the best dinner we had. There was no real menu here. The chef asked us, "What do you like?" and started bringing out course after delicious course.

***You will find house wine at most restaurants. Don’t be shocked if you thoroughly enjoy these wines (and the price per fiasco (bottle)). You are in one of the best wine regions in the world after all, so of course the house wine is going to be phenomenal. 

Where to drink wine:

Besides the obvious answer of “everywhere,” here are the places we visited:

  • Castello di Verrazzano - This was our first stop! A gorgeous property atop a hill with 360 views of Chianti. We also tasted olive oil on our visit here - get ready to be shocked by olive oil and possibly fall in love with drenching plain bread in quality olive oil...
  • San Felice - This winery was mentioned in the 'Where to stay' section earlier as the grounds were stunning! The wines were equally impressive.
  • Antinori - There is a chance you've seen photos of this gorgeous property (modern architecture with spiral staircases hidden by vineyards). You can book a wine tour and/or tasting ahead of time or head there on your own for lunch and wine tasting in their wine shop on your own time. This was one of our later stops on our trip, so we opted for the latter option after already hearing the history of Chianti Classico about 10x.
  • Castello di Volpaia - This is an ancient village built, literally, on wine production. Book a tour and wine tasting here and spend some time in this cute place. There is a small bistro you can eat at as well!
  • Castellare di Castellina - Not only were these wines delicious and the views amazing, but the thing that stood out to us was also their wine labeling. Each year, a bird is chosen for each wine they produce and a painting of that bird is featured on each wine of that vintage.
  • Castello di Radda - Here we had a private wine tasting in our own second-story room with large windows overlooking the vineyards. The wines were poured for us and we were left alone to taste and hang out by ourselves! Again, the wines were amazing.
  • Ricasoli (Castello di Brolio) - This is another village worth visiting for a tour and tasting! This was an actual walled-in castle that felt straight out of a fairytale. There is a wine-tasting room off the main castle grounds and a restaurant hidden in the trees where you can have lunch and/or taste more wine. This is also the location where (apparently) the recipe for Chianti Classico was founded.