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!

A Day in Cinque Terre

A rainy Sunday was the start to our second full day in Tuscany, and it wasn’t any less delightful!

I’ve seen photo after photo of these 5 coastal villages-and yet I still wasn’t prepared for how amazing they are!

When planning this adventure, I actually opted to book this Day Tour through Viator (new customers get $10 off their order when you use my link!), because it eased a lot of the transportation concerns for us. We left at 7:30 in the morning from the Santa Maria Novella Train Station on a bus and drove just short of 2 hours to La Spezia, an industrial city just at the base of the mountains leading to 5 tiny coastal villages ranging from populations of 300-3000 people.

On this trip, we visited 4 villages: Riomaggiore, Manarola, Monterosso, and Vernazza.

The weather made for some overcast photos, but I like to think they still captured the beauty of the villages and the fascination that surrounds the brightly colored buildings and blue waters.

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My favorite thing about taking tours like these, is that there is someone to guide you to the best photos and history in the area, but you also get the opportunity to explore independently and find your own gems. Plus, you’re sure to meet some interesting people-and even make some new friends!

Some of my favorite shots from this trip (PS, all of these photos were taken by Zainab and I on our iPhones!):

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When it comes to shopping, none of these villages really tickled my fancy. There are lots of small, rather pricey shops-which I’m sure ties into the whole “Population: 300” thing.

We did have an amazing blackberry tart at a small cafe in front of the ocean in Vernazza, some super strong caffe correto (espresso+grappa) in Monterosso, where I think we also found the small place that made fresh lemon slushes….and had an option to add vodka.

We added vodka, obviously.

I think moreso than anything, I was too busy taking in how beautiful and well-preserved these little villages were to get too preoccupied with the wares they offered. I saw a lot of the same kitschy and touristy trinkets and small bottles of liquor and oils that you can find most anywhere in Italy…so I stopped worrying about where to shop and what to buy and just enjoyed the ocean instead.

It’s worth noting that there is a train that goes from La Spezia into the villages. It’s very fast, and rather efficient! At the end of the day, there were at least 400 of us piled on the platform waiting for a train that was delayed over 30 minutes…and things got real. People were pushing and arguing and being rude! And it took FOREVER to get off of the train and to the meeting point with our bus because of the crowding and lack of manners!

But I had expected way more tourists and crowding, especially on a Sunday. I was pleasantly surprised at how we had a lot of room to breathe as we made our way through Cinque Terre, moreso during the first half of the day!

This trip really made me want to focus more on the Italian coast on my next trip (although I just have such a love for Florence, and will probably start/end there always), because it really is one of the most beautiful, natural wonders. Sprinkled with history and character, it really draws you into its charms!

Have you been to Cinque Terre? What were your favorite things to see and do?

Happy Travels!

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