Tuscany | Italy

If you’re a regular follower of our European adventures you know that we average 3 days per trip. Italy is one of those countries where 3 days simply will. not. work.

During my undergraduate studies, I studied abroad outside of Rome and fell in LOVE with Italy! It’s such a large country with many different cities to explore — but Tuscany was the main area I have always dreamed of returning to one day with my spouse.

This post (+ the 2 following) will highlight our 8 day itinerary through Tuscany — the Siena region, Florence and Cinque Terre!

Day 1:

We flew into the Pisa Airport mid-afternoon, where we picked up our rental car, and immediately got on our way to our first stop!

Lucca is an adorable, quiant Italian city just 30 minutes north of Pisa. We enjoyed a late lunch just inside the city walls at Pizzeria In Santa Maria.


After a bit more exploring — we made our way back to Pisa to quickly see (and of course, grab a photo) with the Leaning Tower of Pisa.

You could definitely spend MUCH more time in both Lucca and Pisa than we were able to — and if your trip allows, you should! (We needed to get to Pari before sunset.)

We spent the rest of the late afternoon driving south along the coast to our first AirBnb in Pari (Province of Grosseto — 40 minutes south of Siena).


I had never heard of Pari before planning this trip — but we knew we wanted to stay a bit outside of the city of Siena. So when I stumbled upon this Tuscan farmhouse in this small, remote, super untouristy town, about an hour south of Siena… we immediately booked it!

Viola is the warm and welcoming Italian host of this AirBnb — she lives on the property and could usually be found baking (or chasing her dogs in the yard)! She made us a farm fresh breakfast each morning (which always included that day’s fresh baked good!) And even has a small “store” where you can purchase local honey, olive oil, pasta sauce, wine, pasta, herbs… you name it!

We enjoyed grabbing some goodies to cook dinner in one night.


Day 2:

After waking up to one of the most beautiful views and breakfast spreads of my life — we got on the road to Montalcino.

We spent an hour or two exploring the city — the fortress, Piazza de Popolo, and the amazing view from Bibliotheca Communal.

We ate lunch at Il Grifo Ristorante — and even though they are known for their pizza — I was too excited about finally being reunited with Ribolita Soup (traditional tuscan soup made with beans and vegetables).


With full stomachs we made our way to Castiglion del Bosco for theirwine experience.

Castiglion del Bosco is a beautiful spa and golf resort with a full winery located Northwest of Montalcino. We enjoyed the “wine experience” with 2 other couples as we got to visit the vineyard, tour the winery, and of course taste their wines! This package included a tasting of 6 wines (including the most popular from the region, Brunello di Montalcino) — with cheese, meat, and bread pairings, as well.

Although pricey, there’s not a single detail missing at Castiglion del Bosco. We would recommend this winery — (unless you’re looking for something really small/family owned).

We had originally planned on stopping at Pari’s natural hot springs on our way back “home” — but the weather forecast was calling for rain so instead we went straight back to the AirBnb to cook dinner and watch the sunset.

But if you’re in Pari — going to one of natural hot springs is a popular and relaxing way to spend your time!

Day 3:

Sadly, on day 3, we had to say goodbye to our favorite AirBnb to date. We gave Viola our best and got on the road northbound… to Siena!

Our first stop was on another Tuscan farm (Le Pietre Vive di Montaperti) where we had arranged a “Cooking Class with Nonna Ciana“. Nonna Ciana is a lovely yet spunky Italian woman who knows a thing or two about Italian cooking — and we were thrilled to learn some recipes and techniques from her and her staff!

This course lasted 4 hours — and cost us 100€ per person. During the 4 hours we learned how to make an “antipasto”, a signature main dish, homemade hand-rolled pasta, and of course, a traditional Italian dessert! — all while sipping on a delicious wines! 

If you’re looking for a Tuscan cooking class — we would definitely recommend this one! It was small and intimate… authentic… informative… and delicious!!

Unfortunately, after getting out of the cooking class, we didn’t have much time to spend actually in Siena — but it was enough to check out the Piazza del Campo and the Duomo. (I have been to Siena previously so we didn’t make this as much of a priority.)


As we continued our drive to our final destination of Florence — we made one more stop in San Gimignamo.

San Gimignamo is super charming — we enjoyed getting lost in the streets for a bit and ended our time in the main square eating gelato from Gelateria Dondoli.

Their gelato is made with organic milk and is some of the best I’ve ever eaten. You’ll know you’re at the right place when you see the long line of people waiting! 🙂

By early evening we had finally made it to Florence!

Click Here <– to read about the following 2.5 days we spent in Florence!

or HERE <– for our time in Cinque Terre!




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