Prone To Wander

Tuscany is known to be one of the most beautiful regions in Italy and one of the most picturesque regions in the world. My husband and I were coming up to our five year anniversary and I knew it had to be special. We spent a full week in Italy but today’s post will be about the road trip we took through Tuscany. 

• Day 1: Florence
• Day 2: Montepulciano, Monticchiello, Sienna
• Day 3: San Gimignano, Pisa, Cinque Terre (Vernazza & Manarola)
• Rental Car Return Day: Lucca
• Map

Day 1: Florence

We started our road trip in Florence. Florence is probably my favorite city in Italy due to its emphasis on Art and all of the walkable attractions. We spent one full day here, (partly due to coming in late from Paris because of a delayed flight), and I would definitely recommend staying longer. Two or three days in Florence is necessary to see the sights and experience the culture. 

We purchased skip the line tickets to see Michelangelo’s David and it was worth every penny! We used “Get Your Guide” to purchase the tickets and the instructions were very easy to follow. We spent the morning seeing the David before it got crowded. One of my favorite parts is the walk up to the David. You are able to see other sculptures that were not finished and they look like they are trying to come out of the marble. 

After the David, we went to Cathedral Santa Maria del Flore, which is the main Duomo in Florence. This is another time it is important to purchase skip the line tickets! We wandered around enjoying the prettiest church I’ve ever seen. I love the greens and pinks that decorate the Duomo.

We grabbed some coffee and a cornetto and headed to Ponte Vecchio. This is the oldest bridge in Florence and where the most condensed jewelry stores are. It is so fun seeing the merchants and everything that is available for sale. 

We walked over the bridge and headed to Relais Piazza Signoria which hosts beautiful museaums and statues for all to view. This area is an integral part of the art emphasis in Florence. 

We ate lunch at the infamous All’Antico Vinaio. We grabbed an amazing panini on foccosia bread that makes my mouth water as I type this. Florence is known for its panini sandwiches and this one truly takes the cake. I ordered the “Summer” sandwich and my husband and I split it. They are huge!! 

After wandering through the tittle streets and alley ways, we had a little tea and dessert at Gilli. My friend recommended this and said it was. A little bouje, but it was so cute! It definitely was on the pricier side but the desserts were decadent. I had an Earl grey, as usual, paired with a tirimisu, because… ITALY. 

After carbing up, we walked to Pizza Michelangelo to see one of the best views in Florence. The steps were under renovation so we walked up the street right next to the stairs. It was a climb, not going to lie, but well worth it! It is always interesting to see the street vendors and the performers. 

Walking back down to the city we had to go to the Santo Spirito neighborhood to find the wine holes. We went to Bebe to order orange wine and sip it in the street. One you’re done with the glass, you put it on the table out front or bring it inside. It is a MUST-try! 

We ended the night with some burrata, tomatoes, and spaghetti. We also topped it off with our first gelato of the trip. Pistachio is always the flavor to pick. A truly successful day in Florence. 

Day 2: Montepulciano, Monticchiello, Sienna

We rented our car and drove out of the city. We headed toward our first stop: Montepulciano. This town is famous in the Tuscany region for its wine! It was an easy 1.5 hour drive from Florence and we walked up the steep hill to the center of the city. The views were INCREDIBLE. I cannot describe for you how beautiful the rolling Tuscany hills looked.

We wandered through the streets and went to the main square. We ended up eating lunch at this beautiful restaurant called, “Cafe Poliziano” with a patio overlooking the view. I would highly recommend eating here!

Then we drove about twenty minutes to the small village of Monticchiello. We went through the windey cypress road and landed at the entrance point of the city. This city has the most beautiful view in all of Tuscany that I have seen. It’s very small and only has about a 200 population. 

We ended this day with staying the night in my favorite Tuscany town besides Florence which is Sienna! Sienna was stunning. There is something about the main square that just draws you in. The main Square is shell shaped and has an incline. There are so many cafes and restaurants around the square that make sitting there magical.

We got a huge slice of pizza for 2€ and I got the best pistachio gelato of my life! I loved wandering through all of the shops and streets. What a charming town! 

Day 3: San Gimignano, Pisa, Cinque Terre (Vernazza & Manarola)

We started our day with going to San Gimignano. We were able to go on market day and I loved seeing all of the fruits, veggies, meats, and clothing. It was such an authentic experience seeing the older Italians purchasing their items for the week. There were a lot of students wanting around on field trips. It was a beautiful stop in Tuscany and very worth it! 

Our hotel was in Forte dei Marmi. We stopped to take our bags there before we drove to La Spezia to park our car at the train station and head to the Cinque Terre! We went to two different towns. First, we went to Vernazza where we walked through the streets and had a beautiful view of the water. Then we took the train to Manarola. You do not have to purchase these train tickets in advance. We showed up and were able to get on a train within fifteen minutes. The trains are the best way to see the Cinque, Terre towns due to their speed and affordability. It’s about 6 minutes to get from town to town on the train.

We had apertive at Norma Dossum and watched the sunset. That was one of the most beautiful views I’ve ever seen in my life. It was truly unreal. I would highly recommend that restaurant because the view was so spectacular. You couldn’t take your eyes off of it! 

Rental Car Return Day: Lucca

Road tripping was the best way to see Tuscany. A few times I felt a little car sick, but I took a less drowsy Dramamine (if you’re in the U.S., the Walgreen’s brand is my favorite) and ended up being okay. I loved seeing the views and stopping along certain view points along the way. To make this trip better I would have added one or two more days to feel a little more relaxed. Overall, it was so memorable and I would want to do it all over again! 

Our Route