Tuscan hill towns are much raved about, and deservedly so. But look beyond well-visited Siena and San Gimignano to find the medieval walled hill town of Montalcino, perched high above the Val d'Orcia. The town looks out over the vines that produce its outstanding Brunello red wines, which can be sampled locally.
From the ramparts of Montalcino's 14th-century fortress, or Rocca, some of the finest scenery in Tuscany spreads out before you: reaching over cornfields, olive groves and hills that dip and rise to the mountains of the Maremma. Try full-bodied local wines in an enoteca, hang out at a cafe on Gothic Piazza del Popolo, or check out Sienese paintings and sculptures in the Museum of Sacred Art.
Hungry? Head over to rustic Locanda Demetra, just south of town, for a farm-to-plate lunch. Atmospheric places to stay abound, including the luxurious Castello Banfi estate, spectacularly centered on a medieval castle overlooking vineyards.
To see Montalcino at its peaceful best, visit early in the morning or in the evening, or choose spring and autumn over summer when it's busy hosting its popular Jazz and Wine Festival. See this 12-day itinerary for trip ideas.
Often eclipsed by Tuscany, central Italy’s Le Marche region is blissfully underrated—but the university town of Urbino is a secret too good to keep. This is where Renaissance superstar Raphael was born and raised. No doubt he found inspiration in the travertine domes and towers of the walled historic center. Cultured, erudite, and easy on the eye, the entire town is a UNESCO World Heritage site.
If ever proof were needed that you can find world-class art in Italy outside of the big cities, Urbino is it. Its pride and joy is the 15th-century Palazzo Ducale, with an arcaded courtyard and a peerless collection of Renaissance art. Here masterpieces by Raphael, Piero della Francesca, and Titian hang in the Galleria Nazionale delle Marche. At the Casa Natale di Raffaello, where Raphael was born in 1483, you can see one of his first frescoes: Madonna and Child.
A sweet, simple, central place to stay the night is Albergo Italia. And don't leave town without trying the season-driven home cooking at the inn where Raphael once lodged, Antica Osteria da la Stella.
Spello, in the Perugia province of Umbria, is a classic hill town beauty that's rarely overrun, even in the peak season. With towers and campaniles rising above higgledy-piggledy houses in honey-colored stone, this is the Italian dream. Its cobbled lanes, worn smooth with centuries of shoe leather, brim with flower boxes and hanging baskets in summer.
Definitely factor in a visit to the Baglioni Chapel at Chiesa di Santa Maria Maggiore to see the Pinturicchio frescoes, and walk up to the Roman arch at the top of the town for sublime views over the hills and plains and a panoramic lunch at Osteria del Buchetto. And to really feel the romance of this hill town, stay overnight at Agriturismo Il Bastione, a medieval farmstead surrounded by olive groves, or 17th-century Palazzo Bocci in the heart of the historic center.
Oh, what views! In the foothills of the Dolomites and just 50 miles north of Venice, Asolo is both delightful and easy to reach. Its backdrop is fabulous, with ramparts offering grandstand views of the surrounding wooded hills and mountains.
Capped by a medieval fortress, the hill town has lanes lined with fresco-colored houses and an 18th-century cathedral sheltering an altarpiece by Venetian Renaissance master Lorenzo Lotto. On the second Sunday of the month, the town is given over to an antique market. And from here, you can easily factor in a day trip of fizz exploring the vineyards of Veneto's Prosecco region.
Right on the main piazza, five-star Albergo al Sole is a romantic base. For dinner, snag a table at family-run Locanda Baggio, on the fringes of town, where dishes are prepared with locally sourced meats and seafood.
Clinging to the slopes of 2460-foot Mount Eryx, Erice offers views over the countryside and coast of northern Sicily, which reach all the way to Tunisia on cloud-free days. This is possibly the most quintessential hill town in Italy, with cobbled alleys curling up to arresting viewpoints, medieval churches, and little piazzas where daily life unfolds.
Though close to the port town of Trapani, Erice feels a world apart. Its crowning glory is the Castello di Venere, where the Romans once worshipped the love goddess Venus. Walk the ramparts for views to write home about. While you’re in town, be sure to sample the Erice’s famous almond dolci (sweets), based on the recipes of local nuns. And for a spiritual sleep, try the peaceful Il Carmine in a former Carmelite monastery.
For Sicily trip inspo, see this seven-day itinerary.
With lushly wooded mountains, the bluest of seas, and soaring cliff faces, Maratea is scenically dramatic. Just above the toe of Italy’s boot, this get-away-from-it-all village has the same winding roads and big sea views as the Amalfi Coast further north, but only a fraction of its crowds.
Once loved by the likes of Frank Sinatra and Princess Diana, Maratea is a heart-stealer. Get out and explore the historic center, sprinkled with 44 churches and candy-colored houses that drip to the sea far below. Maratea’s biggest landmark might remind you of Rio: a statue of Christ the Redeemer with arms outstretched. Clamber up and above the town to the ruins of the original Greek settlement for more uplifting views.
Locanda delle Donne Monache, a chic boutique hotel in a converted 18th-century monastery, makes a wonderful escape, with its quiet gardens and pool.