The Perfect Tuscany Day Trip

My Journey in Northern Italy

Tuscany is a region in Northern Italy that I have been dreaming about visiting for a while. Thankfully, during my family trip to Switzerland and Northern Italy in May 2018, I got to visit the beautiful wine region of Tuscany through SitInMySeats Travel. During this day trip, my family and I got to visit the enchanting medieval towns of San Gimignano, Siena, Monteriggioni and a vineyard in the Chianti wine territory.

Read all about my memorable experiences in each of these amazing Tuscan towns.

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Travel Solo but Never Alone

San Gimignano:

There is a certain look to Tuscany that everyone from all over the world recognizes. From luscious rolling green hills to stunning vineyards and Italian Cypress trees to stone houses, it is hard to not fall in love with Tuscany!

If you are looking to go to that typical picture-perfect Tuscan village, then San Gimignano is just that place! San Gimignano was our first stop on the tour, so the moment I stepped off the bus for the first time that morning I was immediately in awe! I absolutely loved the scenery, beautiful medieval towers, 13th century fortress walls and just the overall atmosphere.

After taking a moment to admire the breathtaking views and let it all sink in, we were ready to start exploring! Since San Gimignano is such a small town, it was definitely a breath of fresh air for all of us since we had been surrounded by endless crowds of tourists in both Florence and Venice the few days prior.

San Gimignano has amazing stores that are perfect for souvenir shopping. My family and I enjoyed looking through the handcrafted shops as well as local food specialty stores. Since the oh-so-delicious truffle oil is a staple in this region, it was a MUST that we purchase a few bottles to take home with us. In case you do not know, truffle oil comes from a rare mushroom and is an ingredient used as a finishing oil in a variety of dishes, both Italian and non-Italian. Some dishes people love to use truffle oil with are French fries, pastas, pizzas, pureed foods, potatoes and eggs. Here in the United States, truffle oil is pretty expensive to purchase, so it definitely makes sense to pick up as many bottles as you can during your time in Northern Italy!

Some other great things to do during your time in the small hill town of San Gimignano is wander through the magical streets, walk into the 12th century Duomo di San Gimignano and climb the Torre Grossa (San Gimignano’s tallest tower and one of Tuscany’s most well known).

In addition to getting lost in this storybook town, another amazing thing to do during your time in San Gimignano is grab some refreshing gelato at Gelateria Dondoli, the world champion gelato shop! That’s right, this gelateria is known to be the world’s best gelato shop and after my experience there, I have to agree that it is! Even though I had gelato for breakfast that day, it was totally worth it because my hazelnut and pistachio cone was to die for! If you go to San Gimignano, you definitely cannot leave without stopping at Gelateria Dondoli!

Click here to discover more to see and do in San Gimignano.



Located in Central Tuscany is the beautiful city of Siena. Known as one of the more popular cities in the Tuscan region, Siena is famous for being a UNESCO World Heritage Site and is filled with gorgeous landmarks and history. Also, may I not forget that the food in Siena is amazing as well!

When I first arrived in Siena, it felt like home for some reason. As I wandered through the city, I realized that it reminded me of the small Spanish city I studied abroad in called Salamanca. Siena is filled with charming narrow streets featuring medieval buildings and a magical selection of monuments and churches just like Salamanca, Spain. It is truly a beautiful city!

*One fun fact about Siena is that it is the main city in Italy where you will hear the most beautiful Italian being spoken! It is so romantic.

There are plenty of must-see spots in Siena and they are all magnificent! The Piazza del Campo is pretty much the starting point when you arrive in Siena. One cool fact about this piazza is that it is one of the biggest medieval squares in the world and has a peculiar shell-shape. Since the 14th century, the Piazza del Campo has been the center of Sienese life! It is the place where residents will gather during an important political event as well as parties and celebrations of all kinds.

When we visited the city of Siena, it was lunchtime so we went to the best pizzeria we ever ate at in the Piazza del Campo called Ristorante Pizzeria Spadaforte (thanks to my friend Ian again for the great recommendation). I got a personal pie with fresh mozzarella, mushrooms, cooked ham with fresh basil. It was amazing to say the least!

After our fulfilling lunch, we strolled through the city a little bit and admired the beauty from all around. Our first stop was to see the Siena Baptistery behind the famous cathedral. Built in 1325, the Baptistery is one of the most important religious sites in the city. Once you go inside, you could admire the stunning frescoes and the bronze and marble baptismal font. When we were finished strolling through the Baptistery, we walked around and saw the outside of the house of the Medici (political building), Torre del Mangia (bell tower) and then made our way to the beautiful Duomo di Siena. Even though we only walked past the Medici building and bell tower, we did make our way into the cathedral, which was so peaceful and gorgeous!


The Duomo di Siena has a white and black façade and the interior includes esoteric symbols and religious stories throughout. After you first walk into the cathedral and look up, you will spot all of the Popes’ heads (both current and past) from above. It is so cool! I also highly recommend making your way into the Piccolomini Library that includes frescoes by Pinturicchio as well as the Piccolomini Chapel where Michaelangelo carved the statues of the four lower niches from 1501 through 1504.

Click here to discover more to see and do in Siena.


The third stop on our Tuscan day trip was to the small fortress town of Monteriggioni. Even though Monteriggioni is so small, it is filled with so much beauty. In addition, this lovely town was definitely the best place to grab a mid afternoon coffee and relax!

Offering immaculate views of the surrounding Chianti region, Monteriggioni represents one of the most important walled castles in Tuscany. The Castello di Monteriggioni (castle) has preserved its intact structure and dominates the surrounding landscape. It was built between 1213 and 1219 for defensive purposes. It is truly magical to see in person! In addition, it is also nice to see the town’s beautiful Romanesque church, Chiesa di Santa Maria Assunta.

Monteriggioni is also a gorgeous town to take a lovely stroll or sit in a little garden and read a book. Since I was so exhausted from walking through Siena and San Gimignano earlier in the day, it was nice to finally relax in one of the gardens and take in all of the beauty surrounding me.

Click here to discover more to see and do in Monteriggioni.

Wine Tasting in Chianti:

Nestled in the heart of the Chianti territory of Tuscany, the Poggio Amorelli estate is where you could taste the amazing wines of Marco Mazzarrini. The man behind the magic is a Tuscan oenologist and agronomist who built Famiglia Mazzarrini – a brand that serves the highest quality of wines bottled at the source and made following the ancient tradition of Tuscan chianti.

When we first arrived at the vineyard, we were given a tour and background of the history and production of Famiglia Mazzarrini. We then were brought into the estate where we settled into a tasting room.


Just like every other wine tasting I have done in the past (which have been many), we tasted a few whites and reds, including a delicious Prosecco. They were some of the best wines I’ve ever had and it isn’t because I tasted them while being in Tuscany. You could tell from each sip that the wine was high quality and our guide even taught us how to properly hold a wine glass. (We’ve been doing it wrong all along and who would’ve known because no one else ever corrected us. Leave it to the Italians who know it all!) In between each wine tasting, we also got to taste the regional olive oil, truffle oil and balsamic vinaigrette on fresh Italian bread. They even served us a charcuterie platter. It was all so delicious!

My family and I loved everything we indulged in at Famiglia Mazzarrini so we ordered a few bottles of wine, olive oil, truffle oil and balsamic vinaigrette to be shipped to our house back in New Jersey. The day those products came to our front door felt like Christmas morning!

Click here to discover everything else to see and do in Tuscany.

I hope you all enjoyed reading about my time in Tuscany. It was truly a magical day exploring these beautiful towns and wine tasting! If you have any questions regarding my trip to Italy, please feel free to email me at, contact me via social media or leave a comment below.

Happy Travels!


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2 Comment

  1. Dear Taylor
    Thank you very much for your story.I just visited Florance and these cities few days ago and was interessting what you would say. Reading your story was great. As if I am there again and have that great experience again. Especially great taste of gelato. Thank you very much for sharing.
    With regards

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