The 4th stop on our trip (after NYC, Barcelona and Florence) was the rest of Tuscany! I know that Florence is part of Tuscany but Florence is it’s own little destination by itself. We spent 3 days in Tuscany exploring all of the little villages and countryside. It was so peaceful and beautiful, I fell in love!
From Florence, we took a train to Siena. The train ride is usually 1 hour and 30 minutes so not an unbearable ride. It stops a few times but Siena is the last stop. Plus it is only $15/ticket. Once in Siena, we rented a car. I definitely would recommend renting a car to explore the country side of Tuscany. But driving in the small villages, like Siena, isn’t the easiest thing ever. Driving in Italy is much easier than I thought.
2 things when renting a car:
1.) bring your state drivers license
2.) most cars are manual and small
The first of our stops in Tuscany was Siena. This is where we stayed the whole time so we made this our little home for 4 days.
Where We Stayed
We stayed in Siena the entire time we were in Tuscany, it was perfect! We stayed at the cutest hotel, Palazzo Ravizza. The hotel is completely restored and enclosed within the walls of Siena. The garden, where breakfast (included in the stay) is served each morning, overlooks the Tuscany hillside. We could have sat for hours just drinking coffee, chatting and enjoying the stunning views! Our room was large, with high ceilings and beautiful wood floors. I would highly, highly recommend this hotel!
Another thing to keep in mind is the small villages don’t allow cars to come into the walls unless a permit is given upon every arrival and departure. Make sure your hotel allows for cars to be parked on their property. Our hotel did and it was great to know we always had a parking spot.
Where To Eat
Osteria La Chiacchiera
A small, local restaurant with great outdoor tables. We went for lunch right when we arrived into town and it was the perfect way to kick off our stay in Siena. We sat outside, enjoyed pasta, cheeses, lots of wine and people watched! I ordered the Penne Pomodoro and Matt ordered the Spaghetti Ragu, we really liked each of our dishes! It had a great view of the street and buildings too.
Antica Osteria Da Divo
This restaurant in underneath The Duomo and is carved out of a series of medieval vaults. We did not have reservations but I would recommend having them. We dined in the medieval vault that was a couple steps down from the first floor. When we first got there, it was just us in the room. Once the room filled up with other people, it was quite stuffy. The room was very romantic so we got over the stuffy air, we were in a cave after all! I ordered the Vegetable Lasagna and it was absolutely delicious! Matt had the Chianti Wild Boar and he loved his too. This was one of the best meals we had in Italy.
What To See
Matt and I wandered the streets and popped into shops and restaurants whenever we saw something we liked. Siena is a relatively quiet town compared to large cities. There are still loads of tourists but not as many as a larger city like Florence.
The Siena Duomo is a medieval Catholic church with beautiful mosaic work throughout the whole church. It kind of reminds me of Alice In Wonderland. It is a beautiful, must-see so make sure you make it inside.
Churches throughout Italy are absolutely amazing! The age, attention to detail and beauty is truly breathtaking.
Matt and I initially went to Montepulciano for the wine…of course! But we ended up wandering around the town too. This is another medieval hill town that was so cute with stunning views of the Tuscany hillside. We stopped to eat gelato, drink espresso and people watch…our favorite thing to do!
Wineries in Montepulciano
Matt and I made zero wine tour reservations. When we travel, we like to wing-it and go with the flow of the day. It is probably out of norm to go to Tuscany and not make wine tour reservations but we’ve been on so many wine tours over the years. For this trip, we wanted to mix it up and go on our own. Most wineries do require tours to be booked in order to visit but we found the wineries where this wasn’t the case.
The winery is named after the founders of the estate but in 2009 was acquired by new ownership. Since it was raining outside that day, we had lunch in their tasting room and sampled 8 kinds of wine. Each wine was described to us in detail and we were also told the history of the winery, it was like we were on our own “tour”. We enjoyed a vegetarian version of the “meat and cheese” tray which was delicious- they did a great job all around!
This is a cellar located in the town centre but the vineyard itself is 2o minutes away. All we wanted to do was sample wines so we were pleased that we could easily walk from the winery around the rest of the town of Montepulciano. Really good wines but aren’t they all in Italy?! I would highly recommend sitting outside. If there is a wait, I would wait. We sat upstairs but it was stuffy and not the ambiance I was looking for.
Winery in Chianti Classico
Located in the heart of Chianti Classico is the Brolio Castle. This is the oldest winery in Italy and second oldest winery in the world! This is where Barone Ricasoli invented the Chianti formula too. Of course, we saved this one for last! We started by walking the grounds of the castle. While walking the grounds of the castle, Matt pointed out all of the ways they would protect their castle from attack. This was a nice discovery after 15 years…Matt has a plethora of knowledge about the medieval times! The grounds of the castle had insane views of the Tuscany hillside.
After we walked the grounds, we went into the tasting room for the wine tasting. Their wine was our favorite from the whole trip. It was by far the best Chianti I’ve ever had. We bought a bottle and enjoyed it that night! I recommend eating at the restaurant on the property, Osteria del Castello.
We drove around Tuscany Countryside to get from winery to winery and town to town. The views, vineyards, and farms were like something I’ve never seen before. They take such great care of their land, it felt like we were in a movie scene driving the winding roads around Tuscany. I would highly recommend renting a car just for this reason, to wander around. We got lost, laughed a lot, cussed a lot (at the car, mostly!) but had such a great time exploring Tuscany with just the 2 of us!
I am obsessed with Italy and can’t get over everything about it. I would highly, highly recommend doing Florence and then the rest of Tuscany. We loved everything about our time in Tuscany and wish we could have stayed longer. The 3 days in Tuscany and 2 days in Florence definitely were not enough. It was peaceful, beautiful, relaxing and the food, people and wine were even better than we could imagine!
A HUGE thank you to Caitlin Hoffmann founder of Wandering Eye Co. for your amazing recommendations and help planning this great trip! She did an absolutely amazing job! I highly recommend her services. We wouldn’t have had the experience we did without her help.
Is there anything you would add to your 3 days in Tuscany?