By Jenny Peters

Back before GPS, making a road trip across Italy’s gorgeous Tuscany and Umbria regions (for English-speaking visitors, at least) meant continually losing your way, missing turnoffs and feeling a bit lost all the time.

Happily, in today’s world, driving across the Tuscan and Umbrian landscapes in search of world-class wines, exquisite farm-to-table meals, off-the-beaten-path places to stay and fascinating cultural experiences is a snap. Just grab a rental car when you land in Florence, the heart of Tuscany (if you can get a stick-shift to save a lot of money) and go!

Florence

TUSCANY
Chianti Set your GPS on a course for Badia in the Chianti region, where a series of unique experiences await. Begin with a visit to the Livon family’s lovely Borgo Salcetino, where they expanded their wine reach after successfully establishing Livon Winery in the Fruili/Collio region of Italy in the northeastern corner of the country. Here in Chianti, two generations of Livons create incredible Tuscan favorites, particularly the Lucarello Chianti Classico Riserva (95 percent Sangiovese, as well as their luscious Rossole, a blend of Sangiovese and Merlot.

For both a fantastic place to sleep and award-winning Tuscan wines, make Badia a Coltibuono in Gaiole your next stop—and home base for a day or two. Since 1846, the Stucci Prinetti clan has been the shepherds of not only the land, the grapevines, and the olive trees, but also the abbey and the ancient Abbazia Di Coltibuono Catholic Church that are on their property. Visit the winery and spend the night inside a monk’s cell, now comfortable bedrooms; the walk down the abbey hallways to your room will whisk you back to the 11th century when this ancient place was constructed.

Badia is also the home of the first cooking school in Tuscany, the legacy of the famed chef (and Stucci Prinetti family member) Lorenza di Medici, who created this fantastic experience in 1983. Take a class, and you’ll return home thinking you’re a genius at fine Italian dining. Don’t forget to taste their olive oil along the way. And, of course, try their Badia a Coltibuono Chianti Classico Riserva for a sublime taste of Tuscany at its best.

Siena Time to head south for an hour to the beautiful walled city of Siena to visit the Piazza del Campo, the central square where the famed Palio di Siena has happened every July since 1633. That slightly insane and positively dangerous horse race among the 17 city wards is a pageant unlike any other; you may have seen it in the Bond flick Quantum of Solace. The whole city is a history lesson, so be sure to allow time to see all the winding and picturesque cobblestone streets of this UNESCO World Heritage site first settled by the Etruscans in 900 BC.

Grosseto You’ll probably begin to feel the pull of the sea from here, making it time to steer toward the Mediterranean. Within this region is Grosseto, a lively seaside town located in the Maremma, the place where the Etruscans lived and roamed the sea, and see archeological sites in Sovans, Sorana or Pitigliano to enter their world. Other interesting sites include the Roman remains of Vulci, Cosa, and Ansedonia. Make the Locanda Terenzi Winery and Agritourismo B&B home base, a gorgeous place run by the Terenzi family. Taste their Morellino di Scansano Sangiovese as you marvel in the view of rolling vineyard hills and the unique Tuscan light.

Duomo-Florence

Visit Parco dell’Uccellina, the wild regional park that meets the sea, via horse-drawn carriage, and learn about this ancient land and windswept beach; and don’t be surprised to see Italian cowboys riding by! Allow a full afternoon to marvel at Il Gardino dei Tarocchi (The Tarot Garden) created by artist Niki de Saint Phalle, with its massive, Gaudi-influenced sculptures. It’s like nothing else on earth—and a breathtaking artistic achievement.

UMBRIA & FLORENCE
Todi Wend east into Umbria, where thermal spas, fine dining, and stunning resorts combine into a sublime experience. At the Roccafiore Spa and Resort in Todi, luxury abounds. The Baccarelli family’s elegant, sustainable resort pairs relaxation and a love of art with excellent food and wines (crafted with local Umbrian grape varietals including Trebbiano Spoletino) and don’t miss seeing the heritage breed Cinta Senese pigs they raise on the farm. Save a few days to enjoy the beauty and pace of this exemplary resort.

Fattoria Colsanto is another don’t miss spot in Umbria, where the Livon family offers up an Italian wine, food and accommodation center with views for miles and world-class wines. As you begin to make your way north back to Florence, there’s one more spa to take in at Bagno Vignoni. Here, at Hotel Adler Thermae, wellness is king. With hot thermal pools (the Romans used these same springs) as its anchor, this five-star spa resort is truly an oasis of calm.

Adler Thermae

Florence Back in Firenze, drop off the rental car and taxi into the center of this beautiful Tuscan capital city. Stay in the heart of town at the stylish Hotel Savoy or choose the Ferragamo-family owned Hotel Lugarno that overlooks the Arno River. No matter your home base, walk to everything here, from the Duomo Cathedral (climb to the very top if you can for views that go on forever) to Michelangelo’s David at the Accademia. See his Medici Tombs, too, then shop (and haggle) at the leather markets nearby. We love the Bargello Museum and the Uffizi, too; and you must eat some gelato before you finally end your tour of Tuscany and Umbria.

For more information on Tuscany and Umbria, visit the following websites: visittuscany.com/en; umbriatourism.it/en; italia.it/en/discover-italy.html.