Stonekings Do Italy… the Best Things to Do in Tuscany Italy

When we last left off, we had said arrivederci to the capital of Italy [AKA Rome] and we headed for the gorgeous and picturesque scenery of Tuscany! **see my Rome travel guide here**

I felt like I had this idea of what to expect when we got to Tuscany–mostly in part to the movie Under the Tuscan Sun–and let me just preface this entire things to do in Tuscany Italy post by saying it sure didn’t disappoint. Our travel agent had set up a private driver to take us from Rome to Tuscany and we were able to stop along the way to check out a few of the smaller cities prior to our arrival at our next hotel.

I’m breaking down each of the towns we visited throughout our trio of days in Tuscany:

The Best Things to Do in Tuscany Italy

Orvieto

We took a little detour before Cortona and went to Orvieto for a little sightseeing and lunching in this quaint and cute little town! It’s a sweet little village located on a cliff surrounded by gorgeous green valleys and where the Etruscan population settled… we stopped into the most amazing butcher shoppe, dined at a highly-recommended bistro called La Pergola for lunch, and then grabbed a few family souvenirs while we visited… olive wood cheese boards and serving utensils, a few handmade pieces of pottery, and a miniature Pinocchio ornaments for the girls. We absolutely loved this town!!!

**while in Tuscany, I fell in LOVE with their region-rich pasta called Pici… if it was on the menu at any trattoria we visited, I ordered it–think of it as super thick spaghetti, very rich and dense and OH so tasty… just trust me on this one and order whenever you find it!!**

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The Best Things to Do in Tuscany Italy featured by top US lifestyle blog Hello! Happiness The Best Things to Do in Tuscany Italy featured by top US lifestyle blog Hello! Happiness; Image of a woman wearing denim jacket and striped dress.Yellow Striped Dress [sold out/shown in black here] | Cropped Denim Jacket | Pochette Metis Crossbody
Floral Headband [sold out/similar here] | Sasha SunniesAudrina Sandals

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Cortona

Once we left Orvieto, we headed to check-in to our hotel, the Relais la Corte dei Papi. David, the owner was the epitome of everything you’d expect from someone that wants to make sure his guests are well taken care of and his family’s resort is truly one in a million… everything was to the nines in true Tuscan decor and grandeur and so peaceful, which was a welcomed change from the hustle and bustle of Rome.

The first afternoon we settled in poolside for a bit of R&R and drank wine before getting dressed for dinner. Luckily for us, the on-site restaurant was absolutely incredible and is situated in the old cellar of the former residence. It had so much character we ate there both nights during our stay and the dishes were unbelievable… the presentation, the ingredients–seriously if you ever go to Cortona this would be my hands down recommendation for dinner!

The next morning, we had a private driver that chauffeured us all throughout Tuscany–hopping from town to town–and checking out so many incredible monuments, famous spots and such, and just taking in the beautiful countryside, while settling into a few cafes for vino, gelato, and caffe of course.

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Montepulciano, Pienza and Montalcino

The first town we visited on our full day of tours was Montepulciano…. we loved the piazzas and the views were to die for!! These two hilly towns in southern Tuscany were ideal for little day trip visits — so much history and tradition everywhere. We did a bit of souvenir shopping, stopped into a cafe for our daily gelato fix AND got to take in a few wine tastings and sample some of their famous vino nobile wines from a local winery with a fun underground tour and tasting with their owner.

And let’s not even talk about the famous Pecorino cheese from Pienza–absolutely incredible and of course we shipped home so we could recreate some fabulous charcuterie trays back at home, too!

Finally, we visited Montalcino–it was an added little bonus once Jeff told our driver how much he LOVES brunello wines and that’s what they are known for. Fast forward to the BEST wine shoppe in town and we sent home SO many bottles… after this, we should be turning into full blown sommeliers ;).

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Pink Jacket | Lemon Graphic Tee [sold out] | Ripped High Waist Jegging | Audrina Sandals | Cosmo Sunnies

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Siena

Hands down my favorite town in Tuscany, Siena has the most incredible scenery all built within its city walls. You may be familiar with its annual horse race, the Palio di Provenzan, which is where each of the 17 historic neighborhoods within Siena compete with horse races to beat out their rivals! When you’re born in Siena, you’re born into a contrade depending on where you live within the city and you’ll remain that animal for your entire life [examples of contrades are the eagles, caterpillars, owls, giraffes, etc]. Seriously, I found this so very fascinating and I’ve been reading more about Siena’s history since we returned home… suffice to say I’m obsessed with all things about this 14th century village. The Piazza del Campo is one not to miss and the Cathedral was one of the favorites we visited as well.

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Cropped Jacket | Blush Jumpsuit | Guana Cay Necklace | High Key Sunglasses

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Chianti

Last but not least… before leaving Tuscany, we got to take in the a town called Barberino Val D’elsa in the Chianti region, how fitting, for a little vineyard visit at the Castello Della Paneretta winery. This endearing castle was picture-perfect and over the top stunning and made me want to stay just a tad bit longer!! Luckily for us, we sent home a TON of wine and a few bottles of their famous olive oil so we can keep this gorgeousness in our minds for many years to come until we can come back.

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Hope you enjoyed this play-by-play of just a handful of things to do in Tuscany Italy… I’m already plotting the next time we visit to check out a few others that came highly recommended, including: San Gimignano, Lucca, Volterra and Arezzo. Next stop, Firenza AKA Florence–back soon for the full rundown!

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4 Comments

  1. Tara
    June 21, 2019 / 9:14 pm

    Natasha…Everything looks so amazing! Thank you for sharing all the details! We’re heading there in Sept. Would you mind sharing the private driver you used to hop through the Tuscan towns? We will be heading to several of those towns as well. Thanks in advance!!!

    • June 24, 2019 / 11:13 am

      thank you.. we had a BALL! actually our travel agent and her italian counterparts arranged all of those through IDI travel!

  2. Tara Barker
    August 4, 2019 / 11:17 pm

    Natasha- Love all the details you’ve given for your trip! We are headed there in Sept & wondering how expensive shipping wine back to US was? Looks like you you sent home wine from both a wine store & a winery? Would love to ship home rather then carry in a wine carrier!! Any advice you can provide would be greatly appreciated!!

    • August 5, 2019 / 11:10 am

      not too pricey at all… tons of the wineries/shops we visited helped us ship everything and made it super simple!

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