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The best places to visit in Chianti

The best places to visit in Chianti

Our Tuscan adventure began in the Chianti region starting with Greve in Chianti, supposedly one of the main attractions in the area. To our dismay Greve was rather uneventful, and lacked the typical medieval Tuscan feel that we were hoping for.

classic Tuscany

We found immediate redemption on a slight detouring just a few minutes down the road in the town of Montefiorale, a quaint little hideaway atop a hill, listed in the renown Italian travel guide ‘Borgi Piu Alta’ as one of the best places to visit in Italy. We embarked on a journey back through time as we walked across thousand year old cobblestone alleys. Everywhere you turned was a picturesque corner, one after the next. One just can’t help but stop and photograph.


The town is extremely small and while there are no restaurants or coffee shops, it’s a great little pit stop if you’re looking for classic Tuscany, minus the crowds.

Afterwards we headed toward Castelline in Chianti driving south on the beautiful Strada Chiantigiana, lined with vineyards, olive groves and beautiful rolling hills. Our trip was pleasantly interrupted by a vibrant village called Pansano, where the bustling life makes a pit stop mandatory.

We joined the small crowd for some people watching and shopped for fresh produce while sipping on a pre lunch espresso. While exploring the little streets of this pretty gem in the Chiantishire we stumbled upon a place that we immediately fell in love with. The view, the flowers, the outdoor terrace overlooking the most incredible panorama, combined with the traditional Tuscan cuisine hooked us.

Tuscan cuisine

Like all good things we discovered magic where we least expected. And as always happens while traveling, a short stop on the side of the road turned into an adventure.

A few minutes later we found ourselves sitting at Trattoria Oltregardino enjoying a plate of gluten-free wild boar pasta, local zucchini cooked with mint and olive oil and garden peas seasoned with local prosciutto and olive oil. They even had gluten-free bread for me as well.

Castellina in Chianti

The view was so captivating that we didn’t want to leave our table. A second round of espresso just to catch another glimpse?
… Better not, the rest of Chianti awaits!

We hit the road again headed for Castellina in Chianti, situated on top of a hill with an unmistakable watch tower visible from afar. Unfortunately we get there in the middle of a crazy storm. The rain is pouring so hard that we can’t get the windshield wipers to move fast enough. We cruise through with the car and continue our journey south, hoping the sun will make an appearance.

Trattoria 2

Our next stop was Radda in Chianti, a medieval town with a charming center, beautiful piazza and the original tunnels still in tact that connect the town underground, dating back to the middle age. This place is home to a few cool rustic restaurants, beautiful aggritourismi and a charming trattoria right in the center. We already ate and were rather quite full, but still couldn’t resist the opportunity to sit outside and people watch.

Gaiole in Chianti

We ordered the local crostone, a sample platter of 4 bruschetta seasoned with tomato, arugula and balsamic, pecorino and truffle, chintasinese and prosciutto curdo.

Why not? We ended up finishing our merenda (the Italian word for afternoon snack) with some local, hand made cantuccini and a glass of vin santo to go with it (a sweet dessert wine perfect to dip the biscotti).
The last destination on our checklist before heading to our Tuscan retreat was Gaiole in Chianti, which was actually a very quick visit, as the town was not as historic and charming as the others. After a brief driving tour we were ready to head home.

We thought about stopping to indulge in another epic Tuscan feast.
But a refreshing dip in the pool and evening in the spa was just too much to resist.

Tuscan feast.
Tuscan feast.2

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  • Bob August 29, 2016 10:39 am

    Beautiful place I must visit with my wife,thanks for great story

    • ambra August 29, 2016 10:49 am

      Thanks so much Bob! That is definitely a very romantic place, so definitely taking your wife there would be lovely!!

  • Vanesa August 29, 2016 10:44 am

    My recommendation also,calm and beautiful!!!

    • ambra August 29, 2016 10:49 am

      Thanks Vanessa, glad you love it there too!

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