The Italian Hotels to Fall in Love With This Shoulder Season

Italy in summer is beautiful, but it can also mean crowded streets, packed restaurants and temperatures that make sightseeing unbearable. Fall offers an easier way to experience many of the country’s most popular destinations as well as a reason to consider a few cities that still fly under the radar or can’t compete with the draw of the Mediterranean or Adriatic from June through August.

Truffle hunting in Piedmont to the olive harvest in Tuscany, the season also brings experiences that are not available at other times of the year but are not worth missing. And after a long day exploring, where you lay your head may be the determining factor to having the perfect trip. Below find a few cities from the north to the south that thrive in the cooler temps. 

Florence and the Tuscan Countryside

Florence is busy for much of the year, but fall brings cooler days and a noticeable change in the surrounding countryside. It is also a good time to divide a trip between the city and a hotel outside it, rather than choosing one or the other.

Viesca Toscana is located about 15-20 minutes outside of Florence and was once the private summer home of Salvatore and Wanda Ferragamo. Today, the estate includes a 16th-century manor, private villas and suites surrounded by gardens, olive groves and mature trees.

The hotel’s Heritage package connects the stay to the Ferragamo family’s history. Experiences can include special access to the company’s historic Florence headquarters at Palazzo Spini Feroni, offering a closer look at one of Italy’s most recognizable fashion names. Guests can spend the day shopping and visiting museums in Florence before returning to a setting that feels distinctly removed from the city.

Closer to Arezzo, Il Borro Relais & Châteaux is a destination in itself. The 1,100-hectare Ferruccio Ferragamo family estate includes a restored medieval village, vineyards, restaurants, villas and artisan workshops. Fall is one of the best times to see it with the Tuscan foliage beginning to change, the evenings becoming cool enough for a fireplace and Il Borro’s red wines. 

The estate’s restaurants that include Il Borro Tuscan Bistro and Osteria del Borro turn toward the ingredients of the season that are found on property. In early November, Il Borro also celebrates the olive harvest. Guests can take part in picking olives, learn about the pressing process and taste the new oil soon after it is produced.

La Prairie recently set up a dedicated wellness and skincare experience at the Tuscan estate, bringing its offerings as well as two exclusive treatments that can be found solely at Il Borro. The residency reflects a shared focus on hospitality, craftsmanship, and wellness-driven experiences that expand on Spa La Corte’s existing treatments. 

Sorrento, Campania

Many towns along the Amalfi Coast begin to slow down once summer ends. Sorrento does not. Its restaurants, cafés and shops remain open, and the city continues to feel lively throughout the fall without the height-of-summer traffic and crowds.

The weather is still pleasant enough to walk through the historic center, spend time by the water and enjoy lunch outside. In the center of town, Grand Hotel La Favorita is a bright five-star property decorated with majolica tiles, Mediterranean colors and plenty of greenery,  with its location making it easy to walk to Piazza Tasso, the Cloister of San Francesco and the city’s main shopping streets. 

The property’s Bellavista rooftop looks across the Gulf of Naples toward Mount Vesuvius and is the best setting for an aperitivo followed by dinner at Zest, set beneath lemon trees. The hotel’s restaurant featured in the Michelin Guide incorporates the famous Sorrento lemons in dishes such as Risotto with lemon, scampi and licorice. 

Nearby, Bellevue Syrene offers a more romantic take on Sorrento. The hotel occupies a former private residence built on the foundations of a Roman villa and has welcomed guests since 1820. Its terraces sit high above the sea, with views across the Bay of Naples. Currently to celebrate its 205th anniversary and in collaboration with Museo Correale of Sorrento, the restoration of Hunting Scene, a painting by the Flemish artist David de Koninck, is taking place inside the hotel. This rare initiative within the Italian hospitality world merges the realms of art and hospitality, offering guests the opportunity to witness the restoration process up close and to experience culture in an entirely new way where art quite literally becomes part of the hotel’s living fabric. 

Lecce, Puglia

Lecce is often used as a base for exploring Puglia’s beaches, but the city deserves more than a quick stop. Its historic center is filled with Baroque churches, small piazzas, independent shops and restaurants that stay lively well after summer ends. Stay at Patria Palace, an 18th-century palazzo directly across from the Basilica di Santa Croce. It is Lecce’s first five-star hotel that has a more contemporary look while preserving its frescoes, marble floors, stained glass and other original details. The hotel’s rooftop terrace is an ideal spot for an aperitivo as the sun sets.