Tuscany is an ideal getaway, especially if you have limited time or are passing through on your epic Venice, Florence, and Rome tour. If you love castles, wine, rolling hills and green fields galore, then Tuscany is the perfect place for you. We spent Valentine’s Day Weekend there with some friends and I fell in love with all things Tuscany. In the Chianti region where we stayed, the towns were located close together so that visiting several in a day was a breeze. Based in Monteriggioni, we visited four villages in the span of two full days. Even though we were there in mid-February, which is the off-season for most things, we still had a wonderful experience and I would go back over and over again! So, here’s a weekend guide of Tuscany and all the points of interest in Monteriggioni, Castellina in Chianti, Greve in Chianti, and San Gimignano. At the bottom, you’ll find a Google Maps guide for reference!

Before you start, I recommend that you either rent a car or drive through Tuscany. I have no advice on bus routes or public transportation here, but in my opinion, it would be worthwhile to be able to drive from place to place at your own pace and see all the sights – not to mention being able to pull over on the side of the road to take breathtaking pictures whenever you want!

Monteriggioni

Just an hour south of Florence, Monteriggioni is a town in Tuscany known for its 13th-century medieval walls and watchtowers.  The old town is surrounded by an impressive wall where you can walk along the top for views of the Chianti region. We stayed at an Airbnb right outside of the castle walls within a short driving or walking distance. The view on the drive to the castle from our Tuscan rental was incredible. Monteriggioni is not only photogenic, but the people are friendly and the food is delicious. There was quite a bit to do for such a small village, even during the off-season of February. I can only imagine how wonderful it is during the summer.

Parking

• We parked for free outside of the castle on the way up the hill (you can’t miss it). There are only a few free spots, so during the summer I’m sure those spots fill up quickly and you have to pay to park. Then, you walk up well-lit steps to get inside the perimeter of the wall.

Where to Eat

• Ristorante Il Feudo – We had lunch here because they weren’t open for dinner. This place is right in the square (Piazza Roma) of Monteriggioni. They had excellent gnocchi and wine selections. The staff was extremely friendly and spoke English well.
• Ristorante da Roma – We had dinner here our first night. Their rabbit tagliatelle is to die for. The others in my group ordered meats of all kinds, from lamb and beef to wild boar. Our server was the nicest man and was so intrigued by us and our stories. We loved being able to converse with him!

Museums to Visit

• Medieval Museum – Although this place isn’t marked on Google Maps, it was actually really neat! Inside they had a great gift shop where you could buy shields, balls and chains, crossbows, and even postcards. We enjoyed a short tour of their collection of medieval gear and they even had a pillory that we could try out.
• Tourist Office – Head on over to the Monteriggioni Tourist Office where you’ll find plenty of guide maps and guidebooks, unique postcards, and more information about the area. You can also buy museum and castle wall tickets here for 2€ per person.
• Museo Monteriggioni – Connected to the Tourist Office, this interesting tour leads you through the different periods and history of Monteriggioni. There are points along the way where you can try on medieval chainmail and armor, see how the soldiers dressed, and view a variety of Renaissance weapons.
• Walls and Watchtower – We were only able to walk along a very short section of the wall because the rest of the wall was being restored. Despite the rain and the restoration, there was still a beautiful view of the Chianti region and of the town inside the wall. Purchase your tickets at the entrance or at the tourist office for 2€ per person.

Points of Interest

• Porta Franca – This is the most well-known entrance to Monteriggioni which faces Rome and is a historical landmark.
• Porta Fiorentina – On the opposite end of Monteriggioni is another historical landmark and the other entrance (or exit) that faces Florence. It has incredible views from the archway.
• Piazza Roma – From this central square of Monteriggioni, there are many photogenic points like the church, the gelato shop, the pizzeria, etc.
• Outside the walls – If you want to get a closer look at the wall, exit the Porta Fiorentina and take a right, where you can follow the path around the wall among the olive trees back to the entrance.

Medieval Museum entrance

pillory at the medieval museum

Porta Fiorentina, the historical landmark that faces Florence

The path along the outside of the wall

Castellina in Chianti

Castellina in Chianti is just a short 40-minute drive from Monteriggioni. Along the way, we encountered views of rolling hills, vineyards galore, and plenty of curvy roads to last me a lifetime! Everything I’d read about Castellina sounded so wonderful and we were ecstatic to visit. Unfortunately, we visited in the offseason AND before noon, when a lot of shops and lunch spots hadn’t opened yet. While we were able to walk the typical Tuscan streets and see the piazzas, most of the museums and castles were also closed. While this was poor planning on our part, I would recommend you add this stop to your summer list!

Parking

• We parked in a lot behind the buildings at Via Trento e Trieste, 48 where the steps up to town led us directly to the town square – Piazza del Comune. See Google Maps at the bottom of the post for better reference.

Places to Eat

• Pizzeria Chiantigiana – We opted for a small pizzeria as it was one of the few places open, and it ended up being one of my favorite pizza places so far since moving to Italy. The owner had just made fresh pizzas and it was a pay-by-the-slice type of pizzeria. We bought beer and a few slices each and pulled up a chair to the sidebar to enjoy a quick bite.

Points of Interest

• Rocca Street – Also known as Via Della Volte, this was one of the main reasons I wanted to visit Castellina in Chianti. It’s a covered tunnel that housed the original street, where the patrons could bypass the fortress. Throughout the tunnel, there are historical landmarks and dates, and other markings on the walls. On the right side, there are windows from which you can see the rolling hills. On the left side, there are boutiques, enotecas (wine shops), cafes, restaurants, and gelato shops. It was even more interesting and beautiful in person than what was portrayed online.
• Rocca di Castellina in Chianti – Right off the main square, Piazza del Comune, is the Chianti Castle. It was closed when we were there but I would’ve liked to visit the inside.
• Overlook – This overlook provides a great view of miles and miles of the Chianti Region. You can find this point via the Google Maps I have included at the bottom of the post for reference. You can’t miss it, with the big Chianti Rooster at this intersection of roads.

Greve in Chianti

Located just 30 minutes from Castellina (or an hour from Monteriggioni), Greve in Chianti was one of my favorite towns on this trip. The square! Oh, all the colors and flowers! Nothing could rain on my happiness parade over the vibe of Greve in Chianti, not even the rain…

Parking

• We parked in the Greve Carpark, by the Town Hall (Comune di Greve in Chianti). It was within walking distance of the town center. And you can’t miss the town hall…the top looks like a castle!

Places to Drink

• Dolceforte di Martini Allegra – Okay, we didn’t eat in Greve but we did try to escape the rain at a neat café that offered some warm drinks. They made amazing Irish coffees and cappuccinos while we relaxed and warmed up in this eclectic bar of sorts.

Points of Interest

• Piazza Matteotti Giacomo – This is the town square. It’s adorable. All the arches!! Need I say more? Okay, actually I will. Along the sides of the square are shops under terraces and archways. There are cafes, restaurants, wine bars, meat shops, boutiques, and souvenir shops, among many other things. There is an eclectic antique shop with wine openers from decades ago and even an artist’s shop with beautiful paintings of the famous villages in Tuscany.
• Verrazzano Statue – The huge statue in the town square is Giovanni da Verrazzano. He was the head of Castello di Verrazzano. You can read more about him here in my previous post.

Wineries

• Castello di Verrazzano – 15 minutes from the center of town, this castle sits atop a hill with magnificent views of gardens and grapevines. We absolutely loved this wine tour. It deserved its own post about our experience and wine tasting. Check it out here.

Typical tuscan hill side

Castello di Verrazzano is located in the hills of Greve in Chianti

San Gimignano

San Gimignano topped all of the villages! I could have spent the entire weekend exploring here. Everywhere I turned, there was a beautiful street, a panoramic view, or a castle! It was pouring rain the entire time, so my pictures didn’t turn out the best.  We weren’t always able to see into the distance, but I can only imagine what it would be like on a clear day. Oh my! I will definitely go back and spend more than a few hours there during the summer!

Parking

• We parked right outside the front entrance, and it was just a few steps and a crosswalk to the town center. You have to pay to park, and there are ticketing machines.

Where to Eat/Drink

• Bar Firenze – We stopped in here to (again) escape the rain and I was delighted to discover they had delicious gelato! The guys in our group had cappuccinos and espressos, as well. The owners of this place were incredibly friendly and actually taught us how to say a few things in Italian and corrected our pronunciations when needed. (I am always grateful for constructive criticism!)

Points of Interest

• Museum of Torture – While I didn’t go in here myself, the guys with me did, and they enjoyed it well enough. Torture isn’t really my thing, but for guys who love war and all things medieval, it was right up their alley. This Museum is on the right as you walk in through the front archway!
• San Gimignano 1300 – This museum illustrates life in the 1300s and inside they have a scale city model. It was incredible!! On the walls were the house family coat of arms and flags from the 1300s as well. I highly recommend stopping in here. There is no charge!
• Rocca di Montestaffoli – This is a fortress with amazing views of the region from atop the wall. Inside the wall is a small park dotted with olive trees and benches.

Shopping

• They had so much great shopping here! And souvenirs! Something for everyone. I saw plenty of stores with medieval clothing, weapons, swords, and shields. The guys loved these (and, admittedly, so did I). The ceramics were beautiful and reminded me of Nove, but much much brighter and happier, with all sorts of paintings on them – everything from lemons to the Tuscan hills. There were many tourist and meat shops, with wild boar being prominent. I managed to find an amazing little shop where they had flavored olive oils like pepperoncino, mushroom, and many other types. They also had uniquely shaped, colored pasta that I took home as gifts to my family when I made a surprise visit shortly after this trip. These are always great gift ideas by the way!

I hope this post has inspired you to visit Italy soon, and hopefully, you can use this weekend guide of Tuscany to see some amazing sights, eat at wonderful restaurants, drink lots of tasty wine, and enjoy the region with your friends or loved ones. For more information about Italy in general, visit my Italy categories at the top of this page for more posts about this amazing country. If you’re looking for even more villages to visit in the Chianti region, I gathered lots of info before my trip from Chianti’s tourist site, which has tons of advice and even more historical background!

Ciao and, as always, thanks for reading! If you loved me, share me!

Summer Rae

Thinking about booking now?? If you’ve never used Airbnb before, sign up with my link here, and you’ll get $40 off your first trip, or use the Booking.com search tool on this page to find great deals and hotels in the area! Every little bit helps me in return!!