Wedged between Florence and Rome, rural Tuscany offers the quintessential Italian experience: sun-soaked hill towns, green and rolling screen-saver hills, romantically fortified farms, and cypress trees marching single file up lonely ridges. We go to Italy to experience the finesse of Florence, the splish-splash of Venice, and the grandeur of Rome, but it's in Tuscany that we find the rustic-yet-elegant essence of Italia.
Built on hilltops for defensive purposes in ancient and medieval times, the lofty perches of Tuscany's hill towns today seem to protect them only from the modern world. After the hustle and bustle of urban Italy, it can be a joy to downshift to a more peaceful pace. With a surprising diversity of scenic lanes, abbeys, and wineries, the Tuscan countryside is a fine place to abandon your itinerary and just slow down.
This is one part of Italy where I recommend traveling by car. Although driving in Italy isn't for the faint of heart, in Tuscany it's a joy on super-scenic small roads — and the best way to lace together the views, villages, and vineyards. Trains link some villages, but stations are likely to be in a valley a few miles from the town center. Even buses can't make it up, up, up into some hill towns — some of the steepest villages have escalators serving car parks at the base of their cliffs.
To connect with the rural charm that's so much a part of our image of Tuscany, stay on a farm — an agriturismo. This kind of rural guesthouse — which must be a working farm to earn the title "agriturismo" — provides a good home base from which to find the magic of the region. Some agriturismi are simple and rustic; others are downright fancy — but all are hosted by wonderful people eager to share their bit of paradise.
Many agriturismi are dedicated to making sure that their guests are as well fed as their cows. Your hosts may even offer you a "zero kilometer" meal, serving food that is virtually all produced on the farm: olive oil, cheese, prosciutto, bread, and wine. That's a meal that's truly indimenticabile (my new favorite Italian word…meaning "unforgettable").
And about that wine: A big reason for visiting Tuscany is to sample the great local wines. The region is dotted with classy wineries elegantly tucked into the hills, and many growers welcome visitors to their vineyards.
But unlike in the US, in Tuscany you usually need to book a tasting tour beforehand (a simple phone call a day or two ahead is usually sufficient). Most tours last an hour, cost about $10, and finish in tasting rooms where, with expert guidance, you'll develop a better appreciation of the fruit of the vines. The by-product: you slowly build up a trunkful of new favorite wines.
The biggest dilemma facing a first-timer in Tuscany is how in Dante's name to choose from the many hill towns vying for your attention. Each has its own appeal, and many are worthy of an overnight. Here are a few of my favorites:
This beautifully preserved jewel, encircled by impressive walls and topped with a grand fortress, is just far enough off the beaten path to keep it feeling genuine. Its long Etruscan history makes for unusually interesting sightseeing for a small town.
The region's glamour girl, with 14 surviving medieval towers, San Gimignano is a tourist trap by day but an evocative and traffic-free delight after dark.
Siena's stunning main square, the Campo, has a gently tilted floor fanning out into a people-friendly stage set, making it the city's proud centerpiece and giving the town a medieval allure. This is the ultimate hill town, with red-brick lanes cascading every which way and an unrivaled spirit that any visitor can enjoy.
This hill town boasts a medieval cityscape like a miniature Florence. With several historic wine cellars and easy access to wine country, it's my favorite base for exploring the heart of Tuscany. Rooms with a view are standard in this dramatically sited town.
Fans of architecture and urban design appreciate this pint-sized Renaissance town with well-planned streets and squares. For a hill town, it's notable for being relatively flat.
This touristy Brunello-wine capital still manages to exude a stony charm. It's mainly a happy gauntlet of wine shops and art galleries.
With a rich architectural and artistic heritage, thriving Cortona is nested in a scenic hilly landscape dotted with grand churches and Etruscan ruins.
While most hill towns are undeniably touristy, in the evening they become the domain of locals, who polish the cobbled streets with convivial promenades. Join in, and imagine the countless peasant backs that bent so many centuries ago to set these ancient, weathered stones into simple perfection.