6 Reasons You Should Visit Italy in the Fall

by Christopher Atwood

Why travel to Italy in the fall? The answer's simple: Italy minus the crowds will make you swoon.  While millions of tourists travel to Europe in the busy summer season, fall in Italy is actually the best time to plan a crowd-free Italy trip.  Not only will your flights be more reasonably priced when you travel to Italy in the autumn, you'll be able to stroll the cities and countryside without ever cracking a sweat.


Traveling to Italy between late September and the end of November guarantees you'll encounter smaller crowds and can enjoy your pick of Italy's best hotels.  In case you need further Italy travel inspiration, a trip to Italy in the fall affords you the chance to:  

But, what are the best places to visit in Italy in the fall? During fall in Italy, locals -- not tour buses -- clamber over the scenic stone streets of Siena and San Gimignano. In Italy's Piedmont region, bordering France, food lovers flock to the annual white truffle fair hosted in the town of Alba.  Closer to Rome, in Umbria's hilly heartland, the woods blaze red and orange on crisp fall days.

Famed for its postcard-like natural scenery, Italy in the fall burns bright with colors – whether it's purple grapes ripening on yellowing vines or sunlight painting medieval towers in golden light.  There are countless cities and towns that make visiting Italy in the fall worth your time, but below you'll find our experts' top 6 autumn in Italy favorites:

PERUGIA (Umbria)

The town of Perugia, the hilltop capital city of Umbria, stands guard over the vineyard-rich valley below. Perugia is a quilt of cobblestone streets, medieval alleys and historic piazzas. Wandering Perugia, you’ll spot centuries-old palazzi (mansions) alongside arch-framed stairways. Food lovers will drool for Perugia’s handmade chocolates – famous throughout the world.  Every October, in fact, Perugia is hosts the 10-day Eurochocolate Festival – an event honoring the many forms of cocoa. Our Italy travel experts recommend skipping the tourist-clogged festival, enjoying a private tasting in one of Perugia's boutique chocolate shops on a less busy week -- you'll observe how chocolate gets tempered by hand and then taste the oh-so-sweet result (a 100 year old secret family recipe).

Perugia Italy

OSTUNI (Puglia)

Known as the "white city" among locals, Ostuni crowns a hill in Southern Italy's picture-perfect Puglia region. Strolling past Ostuni's whitewashed homes, you'll gaze out across a sun-soaked horizon. In the distance, you'll catch a glimpse of the sapphire-blue Adriatic Sea.  Countless olive trees and vineyards pepper the golden valley below.  Medieval details burnish every corner here -- from the sandstone bell towers of centuries-old churches or the carved facade of Ostuni's basilica.  Nearby, you can bike past olive groves in the Fasano region or learn to make orecchiette pasta with a real Italian nonna (grandma). Click here to download our sample PUGLIA itinerary.

Ostuni Puglia Italy


Fall is the best time to savor the soul of Tuscany – dotted with small-batch vineyards and historic towns, like Montalcino and Pienza.  In the countryside outside of Montalcino, you might enjoy an exclusive wine tasting in the company of a trained sommelier -- savoring sips of the world-prized Brunello wine  grown and produced only here. At the Poggio di Sotto vineyard, you can uncork a taste of Tuscany with the vineyard owner himself.  The vines of this estate overlook the tranquil Orcia River -- framed in brilliant fall foliage and fruiting vines. You might overnight nearby at the historic wine estate Castello Banfi -- a 12th-century castle surrounded by 7,100 acres of vineyards and olive trees. Click here to download our TASTING TUSCANY itinerary.

Montalcino Tuscany Italy

ASSISI (Umbria)

Perhaps most famous as the birthplace of St. Francis, the beauty of Assisi needs to be seen to be believed.  Like many towns in Umbria with medieval origins, Assisi is perched atop a hill.  Here, visitors can tour the massive Basilica of St. Francis – adorned with the 13th-century frescoes and art of Italian masters like Cimabue and Giotto.  The Rocca Maggiore is the city’s fortified citadel – dating to 1173. From the citadel’s perch atop the city, you can drink in sweeping views of the foliage-filled valley below. Click here to view our sample UMBRIA itinerary.

Italy Umbria Assisi

RAGUSA (Sicily)

As Italy's southernmost region, Sicily stays sunny much longer than the rest of the Italian boot.  So, if crisp afternoons and wool sweaters aren't your fantasy of fall in Italy, head to Sicily's scenic shores.  This island gem boasts sun-soaked coves kissed by warm breezes -- all paired with rugged natural landscape, beautiful Baroque towns and ancient ruins. The Sicilian hilltop town of Ragusa, located in the isle's stunning southeast, vaunts epic views of Sicily's craggy valleys and is within easy driving distance of the Sicily's sandy beaches and undeveloped dunes.  With temperatures in the mid 70s well into October, sun worshipers can still savor a day by the beach during fall in Sicily. Click here to download your free travel guide Sicily itinerary.

Ragusa Sicily Italy

ORVIETO (Umbria)

Orvieto is consistently ranked one of Italy’s most beautiful towns. Built atop a flat bluff overlooking a vineyard-blanketed valley, Orvieto rises high from the cliffs below. Visible from far in the distance, Orvieto commands the gaze of any and all onlookers driving through Umbria.  Inhabited since the time of the Etruscans, Orvieto became a center of power during the medieval period – frequently visited by Popes between the 12th and 16th centuries.

Strolling the city’s medieval streets, visitors will notice Orvieto’s striking cathedral – featuring black and white stone and an ornate façade. It's also the ideal jumping off point for day excursions into Umbria's scenic wine country -- where you can enjoy a private wine-tasting with the owners of a castle or savor a home-cooked at an Italian family's farm.  Fall is a bustling time in Umbria -- as the region's countless grape vines and olive trees are harvested in the autumn season.

Umbria Orvieto Winery

Ready to fall in love with autumn in Italy? Just click the button below to start planning your dream vacation with one of our Italy travel experts:

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