A Romantic 4 Day Tuscany Itinerary (Chianti Region in Italy)
Summary: An example 4 day Tuscany itinerary across the Chianti Wine Region that will show you the most beautiful parts of Italy. It includes things like renting Vespas, taking a pasta cooking class, and more!

Disclaimer: Some of the links in this post are affiliate links which just means I make a small commission if you purchase from them with no additional cost to you!
This might be a controversial opinion, but rural Tuscany truly is one of the most beautiful places I’ve ever seen. It has an untouched rustic charm while inspiring awe around every twist and turn of the mountain roads. That said, Tuscany is a large region and everything is very spread out, so where exactly should you go to see the best of it?
I spent a few days slowly exploring the Chianti region of Tuscany. We chose this area because Chianti wine is one of my favorites, so I wanted to be right in the heart of where it’s made. This section of our trip made for the perfect relaxing, but still adventurous, bridge between two larger cities we were visiting.
The Difference Between Tuscany and Florence
When we hear people say “Tuscany,” we often think of rolling hills, wineries, and beautiful landscapes. While that’s pretty accurate for rural Tuscany, the geographical region of Tuscany also includes the city of Florence, or Firenze! So, if you say you’re taking a trip to “Tuscany and Florence,” most people will likely know what you mean, but it sounds a bit funny if you’re familiar with the different regions of Italy.
Different Regions In Tuscany
While Tuscany is a region of Italy, it’s also made of 10 provinces:
- Florence
- Arezzo
- Grosseto
- Livorno
- Lucca
- Massa Carrara
- Pisa
- Pistoia
- Prato
- Siena
To confuse things even more, there are also wine regions in Tuscany that aren’t necessarily official geographical regions, but they are used to distinguish Italian wines. A wine region can span through multiple provinces.

Chianti is one of these wine regions! It spans across Florence, Arezzo, and Siena, and you’ll see a lot of the little towns in Chianti are located within the triangle of these three provinces.
When looking at a map, you’ll also notice several towns with Chianti in the name: Greve in Chianti, Gaiole in Chianti, Castellina in Chianti, etc. These are all different villages in the Chianti region that are relatively close together and make for an excellent road trip to see them all!

Where to Stay in Chianti
In my opinion, if you’re going to be staying in the hills of Tuscany, it doesn’t get much better than a castle winery with acres of rolling hills surrounding it. This was my only requirement when looking for hotels and to my surprise, there are a TON of options like this. Honestly, it’s probably hard to go wrong when you’re in this area, but I’ll tell you more about the castle we stayed at.
Castello di Meleto is located in Gaiole in Chianti and it is genuinely one of the most beautiful places I’ve ever stayed. The view from the castle is awe-inspiring with vineyards as far as you can see.


They offer a few different types of rooms on the property. We were traveling with three couples, so we opted for the 3-bedroom apartment which was perfect for us. It came with a fully functional kitchen, living space, and three bathrooms for us to use. It also included access to two pools, one of which was mere steps from our door.
Castello di Meleto has a tasting room, so you can also just come for the day and experience it if you don’t have a lot of time. They specialize in Chianti wines, so most of them are red, but they had a few whites and sparkling options for us to try, too.




How Long to Stay in Tuscany
We stayed in the Chianti region of Tuscany for 4 full days before heading into Florence to explore the city. I thought this was the perfect amount of time to be able to slowly explore this area without feeling rushed. This post highlights a 4 day Tuscany itinerary, but you can always add to it or subtract from it to make it your own.
If you don’t have as much time to spare, you can always opt to stay in Florence and embark on a day trip to Chianti or other parts of Tuscany. I would recommend doing this if you don’t want to drive, or if you’ll only be in Florence for a short time.
How to Get Around Tuscany
You’re going to want to rent a vehicle when you’re visiting rural Tuscany. We flew into the Bologna airport, rented a car there, and drove to our accommodation. From there, pretty much everything we did was at least 30-45 minutes away. I’m sure there are taxis or cars for hire in this area, but we drove so much that relying on that would have likely been an unnecessary hassle.
If you’re visiting from the US, you’ll need an international drivers permit to drive here. All you need to do is visit your local AAA office and they can handle that for you. It doesn’t take long at all, but to legally drive, it’s needed.
I’ll also note that the roads are generally very narrow and curvy. We had a few people in our group get sick from all the twists and turns. They are prone to motion sickness, though, so if that’s not usually an issue for you, you should be fine.

4 Day Tuscany Itinerary
Day 1: Check Into Your Hotel + Wine Tasting
I always like to take things a bit easy when I first arrive somewhere just to get my bearings and avoid rushing around as much as possible, so that’s exactly how this 4 day Tuscany itinerary will start.
When you arrive in Tuscany, drive to your hotel and check in. If you’re staying at Castello di Meleto or a similar winery hotel, take a walk around the property to really soak it all in. It was incredibly tranquil here and it’s definitely worth spending some time taking in the vastness of the scenery and the surrounding views.
When you check in, ask the attendant about the wine tasting schedule. If you can reserve a time that first afternoon, that would be a perfect way to spend the first day. Get to know your surroundings and the wine it has produced!
Castello di Meleto has a restaurant at the bottom of the hill and you can check for available reservations when you check in. We were able have dinner here on our first night and it helped get us so excited to see more of Chianti on day 2. We ate incredible pasta, drank delicious wine, and listened to a cover artist play our favorite songs all night.

Day 2: Rent Vespas in Chianti and Explore
On the second day of your 4 day Tuscany itinerary, I’d suggest exploring the many little villages within the Chianti region. Renting a Vespa and pretending you’re the main character in a romance movie is the perfect way to do this!
Yes, you still need an international driver’s permit to drive a Vespa. Also, I’ll add that I had very high hopes for my ability to drive one of these. I didn’t think it would be difficult and to be fair, it probably wasn’t. I tend to have a lot of confidence in my abilities, but then become a scaredy cat when the time actually comes. It was a lot more terrifying than I originally thought it would be and I ended up riding on the back of my fiance’s Vespa. Arguably, this was much more fun! He and his dad both have a lot of motorcycle experience, and they were very comfortable driving.

We rented Vespas from Chianti Family Rent. If it matters to you, these are an off white color (some people love the red!). The rental process was easy. We filled out waivers and the owner gave us a few lessons and pointers, and we were off.
If you end up not wanting to rent Vespas, that is totally fine. Just drive your car to the different areas!
Here are a few villages that we explored:
Gaiole in Chianti
While Castello di Meleto is in Gaiole in Chianti, there’s also a little town that you can drive into and explore for a bit. We had a cappuccino at Bar Centrale most days here. There is also a grocery store if needed, and a few specialty shops if you’d like to take home some Tuscan pottery.


Radda in Chianti
Radda in Chianti is incredibly picturesque. There’s a small town here with buildings lining the hills that it’s built on. You can easily spend an hour or two walking around this town. We came here for dinner one night and ate a restaurant aptly named Pizza Pie with delicious pizza that the locals even seemed to enjoy.
Castellina in Chianti
We didn’t spend much time exploring this area, but I wanted to add it in specifically for this one restaurant: Ristorante Albergaccio di Castellina. We stopped here for lunch on our Vespa adventure and nearly had the place to ourselves. The food was tasty and the scenery surrounding it was magic.

Monteriggioni
Monteriggioni is a medieval walled city in Tuscany that makes you feel like you just stepped back in time. There are lots of things to do here for all types of interests with plenty of shops and restaurants to explore. There is also a lot of history with the medieval watchtowers and churches. When visiting this town, you’ll park in a parking lot and then walk uphill quite a bit, so just be prepared for that! It’s worth it.


Greve in Chianti
Greve in Chianti is larger than all of the towns above. We stopped here for lunch on our way from Chianti to Florence. Ristorante Pizzeria La Cantina had excellent pizza and gelato if that’s what you’re craving. This city is very similar to lots of small Italian cities with different stores, restaurants, cafes, grocery stores, etc.
Day 3: Pasta Cooking Class in Siena
This happened to be my favorite day we spent in Tuscany. You’ll want to book this cooking class before you leave for your trip to make sure to get a date that works well for you because it will likely sell out.
Late morning, you’ll arrive at Simone’s farmhouse that looks like it belongs on a movie set. It’ll require driving over some very bumpy roads, but you’ll come to an adorable stone house surrounded by vineyards. You’ll also be greeted with a glass of incredible wine which you can refill as many times as you’d like!


Simone will already have the cooking supplies laid out for you and you’ll get started making fresh ravioli and tiramisu. Simone makes this class so much fun and you’ll leave having learned how to make some of the best food you’ve tasted.

When you’re done preparing everything, you’ll get to explore the property, take some photos by the vineyard, and continue drinking wine while Simone cooks the pasta for you. Then, you’ll sit down as a large group and have a late lunch together.

Experiences like this are what truly make me love travel. Meeting new people in a tour or class setting is perfect for an introvert like me who wouldn’t normally go up to someone to start chatting.
Day 4: Visit Nearby Vineyards
The last day of this 4 day Tuscany itinerary will include visiting a nearby vineyard or two to taste some different wines. Of course, if someone in your group is driving, they can’t drink with everyone, so you may opt for a car hire or a group tour for this day if that would be an issue.
Castello Vicchiomaggio would be an excellent option to drive to. This is a beautiful estate with sprawling Tuscan views and delicious wine. They offer tastings daily, but I would recommend making a reservation online so they know you’re coming.
If you’re not staying at Castello di Meleto, this would be a great time to visit this castle as well. Like I mentioned above, it’s simply beautiful and should not be missed!
There are countless wineries in this area to choose from, so you can also ask your hotel for nearby recommendations to get a local’s perspective.
I hope this Tuscany itinerary was helpful in planning your trip to the Chianti Wine Region! Don’t hesitate to reach out on Instagram with any questions.