Pisa, San Gimignano, Chianti, and Siena!


My first trip to Italy was the type of vacation where we had a lot of ambitious ideas for what we’d like to do, but got there having done so much at home that we ended up truly vacationing. Walking, drinking a lot of wine, eating a lot of food, and then drinking more wine….if it was too late for more caffe.

This time, we wanted to make sure we saw the things we didn’t get to see last time around! One of the main places on our list was San Gimignano in the Tuscan hills!

It turned out, I found this amazing tour for under  on Viator (you get $10 off with that link!), and it took us to Pisa, San Gimignano, stopped in Chianti Classico for lunch and wine tasting, and then to Siena to round out the day before heading back to Firenze.

As I mentioned before, I’m not too bougie to book a tour when it comes to traveling! It’s a great way to cover a lot of ground in a day, and to make sure you don’t miss the highlights!

Speaking of highlights, here is the best of this day tour through Tuscany!

Pisa

We started early in the morning at the Santa Maria Novella Train Station (and got there just in time to grab cappuccino and cornetto before the morning started), and boarded a double decker charter bus on our way to our first stop- Pisa! We were dropped off just outside of the famed Miracle Square, home to the Leaning Tower, church and duomo.

This part of Pisa doesn’t have much to see outside of the main square, which even early in the morning on an overcast day was full of people on the ground, in the air, and just all over the place trying to get their own tourist-y photo with the tower! Pisas beautiful historical center is a marvel with the detailed marble buildings and walkways!

San Gimignano

After we boarded the bus from Pisa, we started through the rolling hills of Tuscany toward San Gimignano.

On the way, our tour guide mentioned that the main piazza there had Gelateria Dondoli, famous for the Best Gelato in the World. I didn’t honestly hear much else after that….oh except something about the Great Pilgrimage, and how the rich built their homes up in tall towers so they could always see who was coming, and how of the 72 original towers, 14 are still there. Whoop, there it is.

San Gimignano is a very picturesque city…every street you take leads to an amazing photo opportunity, and there is an amazing white wine called Vernaccia that is specific to a type of grape only grown in this region! Of course, I bought some.

Also, yes we got gelato! I got organic strawberry and Zainab got a Saffron specialty flavor. Both were definitely amazing, but it’s hard to say the best in the world because all of the gelato in Italy kinda tastes like the best in the world…am I right?

Chianti Classico

Speaking of wine! After heading out of San Gimignano, we headed to Chianti Classico to the Casa Frassi Winery for wine tasting and lunch.

I cannot stress to you how much I love this place. From the moment we pulled in, it was the enchanting scene you dream about when you dream of a winery in Tuscany. The owner walked us through three of his wines as we overlooked the ever-rolling hillside, and then we went into what used to be a monastery (and is now the dining room) to enjoy a three course lunch. I snuck out of lunch a little early to buy some wine and olive oil to ship home, and took the opportunity to profess my love to him in the hopes that he’d let me move there and live happily ever after-which didn’t seem to woo him much. Lol.

Siena

Siena has some of the most breathtaking architecture I’ve ever seen. Grand churches and squares and even the banks are built with crazy details like heads carved into the trim of the building. This part of Italy is also very strict to this day on neighborhoods and family, and being born into your neighborhood. We actually were there on a “Bank Holiday” and got to see a parade, and all of the 14 flags/crests of each commune. It was pretty amazing!

Just before it was time to head home on the bus, we stopped at a cafe and had a coffee granita drink and it was the perfect end to a long day on our feet!

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