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 Tuscan Adventure

I got back from Italy about a week ago, and I’ve had a little trouble adjusting back to that pesky thing we call reality.

My love affair with Italy started before I can remember, largely due to my heritage being partially credited to the country. I love authentic Italian cuisine, music, and culture.

This year, I took what I learned from my trip in Fall 2015 to try to make an even better experience possible, and I’m pretty pleased with how it all worked out!

For this adventure, I scored a $668 RT flight out of LAX and right into Florence, Italy where I planned to stay. I booked this flight last October, but I was tracking the flights using Skyscanner, my favorite flight tracker/predictor site, since May!

Once my flight was locked in, I hit AirBnB to find the perfect apartment to use as my Florence launchpad for my Tuscany plans.

When I originally started planning, I didn’t even have a travel companion. But I had dates, tickets, and reservations….and faith that everything would work itself out accordingly. But of course, my amazing friend Zainab once again came through and was my travel companion!

IMG_1478.JPG

Zainab and I outside the Cieto Chiarli Winery in Bologna

There is truly something to be said of friends who travel together. I look forward to more adventures with her…and we will succeed in stealing Alex away with us next time!

Once all of the most important arrangements were made, I had plenty of time to “map out” an itinerary of sorts, to make the most of Florence and the surrounding areas. Last time, we spent 4 days in Rome and 3 in Florence, and I regretted not having more time in the heart of Tuscany!

Ideally, I wanted a few free days to roam the city and re-visit some of our favorite things from the last visit (which actually weren’t places, but more along the lines of specific types of potato chips and candy bars, lol), and also a few days outside of the main city exploring-there will be more involved posts for each day trip, soon!

My favorite way to book Day Tours and experiences is using Viator, a site/app that books for you via the various companies across the world to get you amazing deals on even more amazing adventures. Get $10 off anything you book when you use this link.

Some of the highlights:

Day 1: Piazzale Michelangelo…and a GELATO FESTIVAL

This slideshow requires JavaScript.

Day 2: Cinque Terre

This slideshow requires JavaScript.

Day 3: Exploring Firenze: Profumo Santa Maria Novella and the best dessert espresso drink!

This slideshow requires JavaScript.

Day 4: Pisa, San Gimignano, Chianti Classico, and Siena

This slideshow requires JavaScript.

Day 5: Bologna-The Food Tour to End All Food Tours

This slideshow requires JavaScript.

Day 6: More Romaing Firenze…Really Making Our Last Day Count! The Leather School, The Central Market, and more!

This slideshow requires JavaScript.

Again, this is a mere taste of all we did! There will be smaller posts later with tips for all of these amazing places to see if you head to Firenze/Toscana!

Want to follow me on the adventures to come (only 53 days until I head to Greece)?

Instagram

Facebook

Twitter

Snapchat: SeeSondraSlim

I love to post my favorite shots on social media, and I always have behind the scenes fun on Snapchat! I’d love to take you along on my adventures! I still have Phoenix, Greece, New Orleans, Palm Springs, maaaaybe New York City, and San Francisco planned for this year!

Happy Travels!

See Sondra Sign-off-stacked