Best places to visit in Italy in September
Tuscany & Expo Chianti Classico
The hills are alive with the sound of…wine corks. September is vendemmia—grape harvest season—and Tuscany is in full swing. One of the highlights? The Expo Chianti Classico, a festival dedicated to the region’s most beloved wine. Expect tastings, vineyard tours, and local food pairings.
Beyond the vineyards, September is the perfect month for scenic drives through the Val d’Orcia, where golden hills and cypress-lined roads look like a Renaissance painting brought to life. Small towns like Greve in Chianti, Montepulciano, and Montalcino host intimate wine events and medieval festivals this time of year, giving you a real taste of Tuscan tradition.
Venice & The Historical Regatta
Venice is back in action after its August lull. The Venice Historical Regatta is a riot of colour, with traditional boats and costumed rowers parading down the Grand Canal. It’s the kind of spectacle you won’t forget.
September is also one of the best times to explore Venice on foot—or by vaporetto—without elbowing your way through crowds. Grab cicchetti (Venetian tapas) by the water, enjoy glassblowing demos in Murano, or get lost in the moody backstreets of Cannaregio. The cooler weather and photogenic skies make it a dream for photographers.
Florence
September in Florence means art, food, and fewer selfie sticks. Explore the Uffizi Galleries, sip negronis on rooftop terraces, and enjoy open-air events under Renaissance domes. It’s also a prime time to dive into seasonal foods like porcini mushrooms and truffles.
Beyond the museums, Florence hosts concerts and cultural events in historic courtyards and piazzas. The early autumn light hits the Duomo and Ponte Vecchio just right, bathing the city in a honeyed glow. And with fashion week-style events popping up, it’s a stylish time to see and be seen.
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Rome
Still buzzing but blissfully less chaotic, Rome in September lets you stroll the Forum without the midsummer haze, when its Trastevere neighbourhood becomes an open-air living room. Warm nights, fewer tourists, and a return to routine means you’ll see real Roman life in full swing: impromptu music, football on in the cafés, families on evening strolls, and wine flowing freely. Evenings are ideal for people-watching or catching a concert in a piazza.
September also brings a sense of calm to iconic landmarks like the Colosseum, Trevi Fountain, and Vatican Museums. With the weather cooler and crowds thinner, it’s the ideal time for long city walks and sunset aperitivos on rooftop bars overlooking the Pantheon or Piazza Navona.
Read These Are the Most Beautiful Historical Sites in Italy to add to your Italy sightseeing wishlist.
Emilia-Romagna & Bologna
Want to eat your way through Italy? Emilia-Romagna is the place. September is rich in local festivals celebrating everything from balsamic vinegar to handmade tortellini. Base yourself in Bologna, a university city with a sharp brain and an even sharper appetite.
Food lovers will also enjoy Modena (home of traditional balsamic) and Parma (known for its namesake ham and Parmigiano-Reggiano). The region hosts plenty of sagre—local food festivals—that offer authentic culinary experiences you won’t find in tourist traps.
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Puglia
Sun-soaked and seductive, Puglia is still gloriously warm in September. Visit whitewashed villages, coastal towns, and olive groves under skies so blue they look Photoshopped.
Head to Alberobello to see its iconic trulli houses, then cool off in the turquoise waters off Polignano a Mare. With fewer crowds, it’s easier to find space on beaches and explore towns like Ostuni and Lecce without a rush.

Sicily
Still sizzling in the south, Sicily is great for late-summer beach days, Mount Etna hikes, and lively local events. September also means fewer tourists at iconic sites like the Valley of the Temples.
You can also catch harvest celebrations and religious festivals like the Madonna delle Milizie. Visit towns like Taormina, Cefalù, and Noto while the weather is still perfect for outdoor dining and coastal drives.
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Cinque Terre
The trails between these pastel-hued coastal villages are much more pleasant to hike once the summer sun backs off. The Ligurian Sea stays warm, so you can still swim without the crowds.
Enjoy pesto-laden seafood dishes in Vernazza, hike the cliff paths to Corniglia, or simply soak in the sea views from a sun-drenched terrace in Manarola. Local harvest festivals also bring extra flavour to your trip.
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Italian Lakes
Lake Como, Lake Garda, and Lake Maggiore offer alpine beauty, romantic boat rides, and crisp air. September is a dream for lakeside picnics and hiking in the Dolomites.
Expect elegant gardens, palatial villas, and the kind of stillness that makes you forget time altogether. Lake Garda is especially good for windsurfing this time of year, while Como’s towns—like Bellagio and Varenna—feel more relaxed post-summer.