Last updated: 10:00 PM ET, Fri October 16 2015

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  • A Cruising Couple | October 16, 2015 10:00 PM ET

    Top Things To See and Do In And Around Chianti, Tuscany

    Top Things To See and Do In And Around Chianti, Tuscany

    Before traveling to Tuscany, we had heard from multiple friends that Florence was their absolute favorite destination in Italy. But although we found Florence to be a beautiful city, we considered the real crown jewel to be just a few hours south: Chianti. The Chianti region of Tuscany is as full of quaint towns and medieval villages as one could ever hope to stumble upon. And then of course there are the countless wineries and stunning vineyards, offering ample opportunities to sip the local wine or simply enjoy the scenery. Ready to learn more? Here are our top things to see and do in and around Chianti, Tuscany.


    While Poggibonsi isn't the most charming of towns, it is the perfect place to base your travels from as it's right in the center of the action. Public transportation is nearly impossible to navigate in this region, so we recommend renting a car to explore the countryside at your leisure. And you're definitely going to want to stop and take some photos of the rolling hills and iconic views along the way. Our car was provided by Economy Bookings and it made for a delightful experience cruising around the countryside.

    Driving Around Tuscany

    Colle di Val d'Elsa

    Just southwest of Poggibonsi is the small medieval town of Colle di Val d'Elsa, which translates as the Hill of Elsa Valley. This small stop on the way to some of the more popular sites turned out to be one of our most frequented visits. The view walking along the exterior pedestrian road offers great views looking out over the valley.

    Colle di Val d'Elsa Tuscany

    Surprisingly, many tourists pass right by the quaint town in search of more popular sights down the road. Our first night in the Chianti Region brought us to Colle di Val d'Elsa when our host recommended us to L'officina della Cucina Popolare. The food and atmosphere were incredible and we would recommend making a stop in town just to eat here. After our delicious meal, we stumbled upon a local street concert that happened to be playing in the park, singing and dancing until well after midnight.

    San Gimignano

    castel san gimignano Tuscany

    Further down the same road you'll find famous San Gimignano. Also known as the Manhattan of Italy, the medieval town was made famous for its skyscraper-shaped towers that resemble those of downtown New York. Be sure to visit the San Gimignano Vernaccia Wine Museum. Even if you don't make it through the whole museum, grab a glass and a seat outside for an amazing view of the surrounding hills.


    You'll likely see the line before you see the shop, and you’ll want to be sure to make a stop. Gelateria Dondoli has been crowned Gelato World Champion multiple times and rightfully so. Grab your favorite flavor and wander the cobblestone streets at your leisure.

    Around Volterra

    O Outside Voltarre Tuscany

    Mentioned in a plethora of popular fiction, Volterra’s biggest claim to fame was playing an important role in the Twilight saga. Volterra is worth a visit if you're a die-hard fan. The town is considered by some to be one of the best hilltop towns in Tuscany. Although the drive and the surroundings are spectacularly scenic, we couldn’t find a parking spot within a few miles of the city walls due to all the tourists. We recommend driving the surrounding countryside and enjoying the vast expansive views instead of fighting for space among the crowded and compact streets.

    Chianti Wine Roads

    Head the opposite direction out of Poggibonsi and you'll end up in the heart of the Chianti Wine Region. Keep your eyes peeled for the black rooster on the gold and red seal that certifies the winery as adhering to the specifications of making the Chianti Classico variety of wine. To qualify as a Chianti Classico wine, it's not enough that the wine comes from this specific area. It must also contain a blend that is at least 80 percent Sangiovese, the red grape typical of the area. The other 20 percent can come from other grapes, of either local or international variety. It's best to call ahead and make a reservation for a tasting, as many wineries do not have tasting rooms that are staffed at all hours of the day.

    Have you visited the Chianti region of Tuscany? Where was your favorite stop?

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A Cruising Couple A Cruising Couple's Column

A Cruising Couple Dan and Casey are the two lovebirds, world travelers and adventurers extraordinaire behind the popular travel blog A Cruising Couple - adventure travel with a dash of class. Their stories and photographs feature that special place where experiential and stylish travel meet. Find out how you can spend less money, live more adventurously and travel more luxuriously on their blog,
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