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Our day in the Tuscan countryside - Pisa, Siena, San Gimignano and Chianti

Pisa, Siena, San Gimignano with and Wine Tasting in Chianti

During our time exploring Tuscany, there was so much to do in so little time. We wanted to visit Siena and Pisa and knew we would have to arrange transportation to get to both places. To make our lives easier, we decided to book a tour with “Get your guide”, a local touring company. I suggest you book directly with them as you will be charged a bit less compared to booking through Tripadvisor.com, either way booking a tour is highly suggested in our opinion – we had such a great overall experience with it and are glad we chose this option rather than blindly planning, arranging transportation, and navigating all on our own. You will get transportation out of it and a bit of a history lesson. Our guides for the trip were Fabiana and Patricia, both Italy natives whom are passionate about sharing their culture with tourists.

Our day started at 7:30 AM where we met our group at the local train station. We got on the bus and made our way to Pisa (1.5 hrs away from Florence). While on the way, the tour guides shared some history facts about the places we were about to visit. Just as a side note, you can choose to take these tours in a couple of different languages. I hope you enjoy the remainder of the post as we break down our time in each individual city throughout the day, where we try to provide some helpful tips to those planning to explore Tuscany.

PISA: Oh man, Pisa is amazing and so worth the trip! If you don’t jump on a tour bus like we chose to do, make sure to plan transportation ahead of time. Pisa is a very small town and you can quickly cover it in less than 4 hours. The main tourist attraction here is the tower as the rest of the city is just neighborhoods. Since this portion of our trip was considered our “free time”, we decided to purchase tickets to go up the tower of Pisa.

The tower of Pisa began getting built in 1173 but was not completed until the year 1300. Due to war and engineer planning to correct the lean the project was put on hold a number of different times. If it wasn’t for these prolonged breaks the soil wouldn’t have had time to compress underneath the tower and it would have eventually fallen over. Luckily, the tower still stands and we are able to climb it, woohoo! Climbing the tower of Pisa was amazing and I recommend it for those who do not have weak legs. As you make your way up, you will notice the change in gravity. Note, this will throw off your equilibrium but is still so much fun to do. Once you reach the top, the view is breathtaking. You’ll be able to see the ­­­­­­entire city of Pisa. If you do visit the tower make sure to check in any purses or backpacks as you cannot bring it inside the building.

After going up the tower, we went into the Cathedral. The art work and architecture inside of the Cathedral is absolutely amazing. If you decide to visit this site, make sure to get a ticket from the main office. The Cathedral is free however the ticket is needed for entry. Additionally, Paul tried a cannoli from “Po’sto Cafe Pisa”. Let me note that this was the BEST cannoli we’ve had in Italy. DO NOT MISS OUT. A fun fact about this area is that the McDonalds here has cannolis, lol, who would have thought?! Oh and the famous scientist Galileo Galilei is from Pisa!!!

San Gimignano For us, San Gimignano was one of our favorite cities in Tuscany. We loved the small city and the history behind it, not to mention the unbelievable views that overlook the city and the countryside.

During the Middle Ages, the city was controlled by patrician families that built over 72 tower-like houses. The higher the tower, the wealthier the family was. While only 15 towers remain, there are a few towers that are open to the public. We purchased tickets to go up the “Torre Grossa” located in Plazza Pecori. We definitely got our work out in for the day, this tower was over 30 flights of stairs and right before reaching the top, you have to climb up a ladder to reach the outside area. Be prepared for this, there are no elevators here nor is it handicap accessible. Once you reach the top area, you will quickly realize that the stair master workout you just did was well worth it. The view at the top is gorgeous. The countryside is breathtaking and the city itself is an unbelievable view. We spent a little bit of time up here as we really enjoyed the view and took some bomb selfies!

After the tower we built up an appetite and stopped at Pizza Al Taglio. We will forever rant and rave about this place because this place had some of the best pizza in Italia! Pizza here is served by the slice which was convenient for us since we were on the go. For dessert we decided to stop at the world-famous Gelateria di Piazza. People from all over visit this place since it is dubbed as the “best gelato in the world” as well as one of the oldest gelato shops with a variety of unique flavors. This gelato shop is located on the corner of the main town square, but no worries you will not miss this place since there is always a line out the door!

Apart from the towers, there is a couple of museums that can be visited here. Also make sure to check our local businesses as a lot of them sell local wine from the Tuscan country side as well as gorgeous Italian plates and serving dishes.


Chianti Part of our tour included a wine tasting in Chianti. The vineyard we went to is known as “Poggio Amorelli,” owned and operated by the Mazzarini Family. We first toured the property and got a quick overview of the family history. The tour was followed by a wine tasting which included various types of cold cuts, breads, and a plate of pasta. Among all the delicious wines, our favorites were the Vermentino Supamente, an extra dry white wine and Grappa Di Vinacce, a dessert wine. We were able to sample truffle oil & olive oil which are also produced by the family. Fun fact, the family spends over 3,000 Euro on every pound of Truffle purchased. Talk about some expensive shrooms! Overall, this was a fun place to tour and would recommend it as a half day activity.

Siena Surrounded by the olive groves and hills of Chianti, Siena is known as one of the most beautiful cities in Tuscany. The architecture and historic sites are all well preserved and maintained by the city officials. The city has made it an imperative to preserve their culture and original gothic-style buildings, making it very difficult to change/update most of the residential buildings. You can see some of the old-style bathrooms attached to the apartments in the town which formerly functioned as communal waste areas – quite interesting. Siena is also home to one of the oldest universities in Italy. 1/3 of the city’s inhabitants consists of students studying there.

One of the biggest attractions in the city is the Siena Cathedral. Built during the 15th century and originally dedicated to the assumption of the Virgin Mary, the Cathedral remains unfinished. Half of the population was wiped by the black plague and Sienna lost much of the wealth and power it held during medieval times. Regardless, the architecture on the Cathedral is stunning. You can see it glow in a light rose color at night and glisten in the sun during the day. Another area to visit is the main square where the twice yearly Palio horse races are ran. This area is surrounded by several restaurants, the town hall, and is also host to a small fountain where everyone stops to make a wish. If you travel here during the summertime, you can watch the horse race take place July 2nd and August 16th with the thousands of locals spectating. It is a once in a lifetime experience – plan your trip accordingly so you can enjoy it yourself.

We ended our trip in Siena visiting a local gelato/tea shop called “La Costarella”. Paul got some mint chocolate chip gelato and a cannoli while I enjoyed an English Breakfast tea and a cream éclair. We wish we would have had more time to explore this city but hey, this is an excuse to come back and visit some other time!




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