Whether coastal or country, Tuscany is made for four wheels. The roads caress every dip and curve of the hilly, pastoral landscape and are banked like a racetrack at every turn. The smaller strade provinciali (country roads) rarely see traffic, and each one offers an enticing scene dreamier than the last: hilltop castles, ancient farmhouses, vineyards, fields of poppies and lavender, and more. It’s worth investing in a great rental, like a vintage Fiat Spider convertible, though a Fiat 124 or souped-up SUV will do. And since this is Tuscany, you’ll want to make time to take in the drive with picture-perfect pit stops. Without further ado, read on for some of the best day trips in Tuscany, and plan your route.
A Fairy Tale
Val d’Orcia is arguably the most visually impressive and romantic area of Tuscany. Listed as a UNESCO World Heritage site in 2004, the lush landscape of hill towns and rolling greens is the setting for a fairy tale. Starting in Pienza, travel south and then east to Monticchiello, a perfectly preserved 15th-century village. Continue on the serpentine route south for 30 minutes to Radicofani, another medieval town with a gorgeous fortress tower. Enjoy lunch at La Grotta, then head northwest to Bagni San Filippo to soak in the natural thermal baths. You’ll be relaxed on your half-hour drive to Castiglione d’Orcia, where you can take in the Val d’Orcia landscape from the town tower. Then, it’s on to San Quirico d’Orcia for more medieval Tuscany and great views. From here, you’ll fall in love with a trail of towns: Take the old SP137 road northwest for 10 minutes to Torrenieri, then go northeast on SP14, a gorgeous ridge road that leads to Montisi. (Make sure to stop at San Giovanni d’Asso along the way). Meander the SP71 road south to Petroio and walk its corkscrew streets. On your way south to Montepulciano, stop in Montefollonico. Tip: You might want to break up the drive into a few days. Every town mentioned is perfect for an overnighter.
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The Wine Route
Wine lovers who love a great drive, welcome to Brunello country. From Montalcino, it’s a short 10-minute drive south to Castelnuovo dell’Abate, where you can visit the radiant travertine and alabaster church of Sant’Antimo and be enchanted by the haunting Gregorian chants at daily mass. About five minutes down the hill is Poggio di Sotto for an excellent Brunello experience. Or, check out Podere le Ripi, whose bonsai wines and farm-to-table Tuscan Garden Experience are a must. Get back in the car for a half-hour drive south to explore three equally delicious medieval hill towns: Seggiano, Castel del Piano, and Arcidosso, where you can have lunch at La Tagliola, a tiny restaurant with a menu dedicated to porcini mushrooms. Then, snake your way northeast on a lazy 30-minute drive, hopscotching from Monticello Amiata to Cinigiano to Porrona. For another taste of Brunello, break at Fonterenza, and then it’s back to Montalcino just in time to catch the sunset.
Art Attack in Chianti
What’s better than a trip filled with art? A trip filled with art, great food, and delicious wine. Luckily, the Chianti countryside offers it all. From Florence, take the winding road to Antinori nel Chianti Classico in Bargino. With six centuries of wine production under its belt, Antinori is one of the most historic aziende (companies). It put Chianti Classico on the map and then redefined itself with an entirely new design — an architectural undulation that blends with the hills. Speaking of blends, the wines here are excellent (a tasting is a must), and the architecture is worthy of your Instagram feed. But you’re here for Antinori Art Project, an ongoing and ever-growing collection of contemporary art installations, including pieces by Tomas Saraceno, Rosa Barba, and Jorge Peris. Hungry? Antinori has a rooftop restaurant — Rinuccio 1180 — overlooking the vineyards. If not, get back in the car and buckle up for a 50-minute ride south on some of Tuscany’s prettiest strade provinciali to Castello di Ama. Installations by artists like Daniel Buren, Michelangelo Pistoletto, and Anish Kapoor can be seen throughout the winery and vineyards. You’re also as likely to unknowingly walk across a Pascale Marthine Tayou as you are to stumble across a Louise Bourgeois.
If you prefer the beach to hill towns, head to Bassa Maremma, about 25,000 acres of coastal paradise from Castiglione della Pescaia to Capalbio. Beyond the beautiful views, there’s plenty to do here, too. Parco della Maremma is a 25-kilometer nature reserve with marshlands, pinewood forests, and pastures. Walk, run, hike, bird-watch, or simply enjoy the dunes. Further south lies Talamone, a picture-perfect medieval town on a wild promontory with a castle. Just south of the town, the natural landscape forms a baia (bay) perfect for wind sports, making Talmone Italy’s top destination for kite and windsurfing. Or, drive 15 minutes south to Laguna di Orbetello, the most important lagoon in the Tyrrhenian Sea — it’s a major migration stopover for thousands of birds and a World Wildlife Fund site. You can explore the oasis via trail and guided tours. For something a little offbeat, another 20-minute drive south and just five minutes inland will bring you to Il Giardino dei Tarocchi, a colorful, larger-than-life art installation from artist Niki de Saint Phalle in the middle of the Capalbio countryside. Not quite your speed? Slow down and drive back north (about 45 minutes) to Alberese, where you’ll meet butteri (true Tuscan cowboys) at Il Bivacco, Italy’s original Wild West show.
Monte Argentario and Island Adventure
Island lovers, take note: Tuscany has some of the most beautiful, wild, and elegant islands in Italy. Driving north or south on the E80, take the Orbetello Scalo exit. Not quite an island, and more like a land strip, Orbetello is a historic town oozing with charm from the moment you pass through the imposing Porta Nuova. Ancient walls, medieval ramparts, Renaissance-era fortifications, tiny streets, and charming boutiques make Orbetello the perfect spot for a stroll. From there, hop in the car and cross an artificial causeway to Monte Argentario, heading straight to the top for the lookout at Punta Telegraph. On a clear day, you can see Giglio, Montecristo, Elba, and Corsica, if you’re lucky. On a rainy day, you’ll be caught up in Monte Argentario’s incredible nature. Take a hike around Capo d’Uomo or grab a bite to eat at Ristoro La Sorgente, a rustic eatery serving local delights underneath flourishing pines. Then, head down the mountain for a spectacular 30-minute coastal drive southeast to Porto Ercole, a tiny fishing village that’s best known as an escape for the rich and famous, thanks to Hotel Il Pellicano. Fun fact: Porto Ercole is often considered to be Caravaggio’s final resting place, though art historians still have this up for debate. Get back in the car, and drive north to the seaport town of Porto Santo Stefano, where the world’s most beautiful yachts and sailboats are moored. You’ll want to walk around the town and enjoy the pebbly beaches. Antsy? Park your car at the port (10 to 15 euro daily) and hop the traghetto (ferry) from Porto Santo Stefano to Giglio, 21 square kilometers of dunes, cliffs, and bays You can return to Porto Santo Stefano for a sundowner.
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Southern Tuscany is wild. Divided from the north by Monte Amiata, the rugged countryside has been almost untouched for centuries. Expect original country charm, amazing food, solitude, and vast vistas. From Montalcino, head toward Sant’Angelo in Colle and pass through Sant’Angelo Scalo for a side trip to Castello Banfi and its museum. Then, make your way to the medieval fortress town of Roccalbegna, which boasts a dramatic location at the foothills of a granite monolith. Have lunch at La Pietra, a family-run locanda that has wowed guests with homemade pasta and locally sourced produce and vegetables for six generations. Continue on to Cana, a medieval town that spans the lengthy crest of a hill, and take in its ancient military fortifications. Next, it’s time for Stribugliano and the great views from Castiglioncello Bandini. For a wine break, visit the vineyards of Fonterenza (more Brunello), then end the day on the hill at Sant’Angelo in Colle for a stunning sunset.
Le Crete Senesi
Stark and haunting, Le Crete Senesi is a vast area in southeast Siena spanning to Arezzo. The landscape of lush rolling hills is at once dramatic and breathtaking. Take an adventurous 45-minute drive southeast from Siena via Taverne d’Arbia to Asciano and explore the town and 11th-century Basilica di Sant’Agata, which was constructed in beautiful travertine. From here, head south on SP451 to Chiusure for a glass of wine at Locanda Paradiso, a local hangout, and gaze at the endless hills. A short drive south on SP9 and you’ll arrive in San Giovanni d’Asso, complete with a magical Romanesque church, then it’s a 30-minute roundabout drive to Abbazia di Monte Oliveto Maggiore, a 14th-century Benedictine abbey with gorgeous library frescoes and glazed terra-cotta. Finally, head back to Asciano on the SP60 road. Stop when you’re ready to take in the Val d’Asso and watch the sunset.
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