Discover the Best of Tuscany: Plan an Unforgettable Road Trip

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Deal Expert, Chicago
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Few places in the world stir our collective romantic wanderlust like Tuscany. Whether it’s the allure of the rolling hills dotted with cypress trees and olive groves or the idea of wandering cobbled streets and sipping local varietals, hitting the open road in Tuscany is a memorable getaway and we’ve got some tips to help you plot your course:

Do balance your time between big and small towns

Lucca
Lucca

Well-known destinations like Florence and Pisa aren’t the over-hyped destinations you may think: they’re brimming with history, museums and restaurants worth a couple days of exploring. Break up the days in lively cities with visits to smaller towns where life moves a little slower – San Gimignano has some of the best gelato in Italy, and Lucca will make you want to re-do your childhood playing within the walls of the city and biking along its perimeter. Striking a healthy balance between Renaissance cities and quaint, cobbled towns will keep the spark for Tuscany alive.

Do schedule wine tasting

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Montepulciano

Look into tours that will schedule and transport you between a couple different wineries to make things easy. The Chianti area is an all-time favorite for sipping its namesake red wine or head to Montepulciano and try famed Brunello. If you’re in the Chianti region, a stop at Antica Macelleria Cecchini is a must to try the butcher’s famed, rare bistecca alla Fiorentina paired with a glass of local red wine.

Do plan around museum schedules and festivals

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Migel / Shutterstock.com

When plotting your course, keep in mind that some museums are closed on either Monday or Tuesday. So if the Uffizi is a must on your list, make sure you head to Florence on a day when it’s open. Italian cities also know how to throw a festival – each town has its own holiday season. Catching a patron saint festival or one of the many yearly parties thrown for Calcio Storico or La Notte Bianca in Florence, Carnivale in Viareggio or the Palio di Siena can make for unique memories.

Don’t neglect the coast

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Tuscany is home to miles of coastline that shouldn’t be ignored. Beach towns like Viareggio are stunning even outside of summer months and the drive along the coast is a scenic way to get from A to B – if you can tear yourself away from the rolling hills.

Don’t fear shoulder season

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Winters are typically mild, and snow is such a rarity that most people living in Tuscany have only seen it a handful of times in their whole life. Without as many tourists around, travelers can have a more authentic experience, get access to shorter lines and take advantage of cheaper hotel rates. A coat is a must, but a romantic evening stroll is still pleasant and Italians have mastered hot chocolate.

Don’t overplan

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And take these tips with a grain of salt. Tuscany may be a well-traveled destination but there are hidden gems yet to be discovered. Leave room in your itinerary to embrace the leisurely pace of life that Italians have made famous – they may be onto something.

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  • Sandra Blackard

    hello