Published 16th Jun. 2025
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Dodge the summer surge and enjoy a holiday to Italy in September. Scale the dramatic Dolomites in the refreshing autumn air, raise your glass in the Tuscan hills during grape harvest season or immerse yourself in Venice’s flamboyant festivities. If it’s thinning crowds you’re after, head south to Puglia’s charming coastal towns, or for sun-drenched sandy beaches, Sicily has your name written all over it. Bags already packed? Read on for our top five reasons to visit Italy in September...
Venice in early September is all about festivals. Plan your visit around the first Sunday of the month to witness the Regata Storica. Dating back to the 13th century, this annual event sees a vibrant procession of ornately decorated wooden boats glide down the Grand Canal, followed by a series of lively gondola races. From boats to the big screen, September also heralds the Venice International Film Festival. Hop over to the Venice Lido, an elegant seaside resort, where you can enjoy an aperitif while soaking up the cinematic buzz.
Image by Olivier Romano
Next up on our list of reasons to visit Italy in September is the heavenly hiking in the Dolomites. With the peak season winding down, walking trails begin to clear and wildflower patches linger in the high alpine meadows. Explore the trails around Cortina D’Ampezzo and keep an eye out for vibrant gentians, alpine poppies and edelweiss.
While some cable cars and hotels start to take a seasonal pause come mid-to-late September, this quieter atmosphere also brings fewer crowds. Around the same time, the Dolomites are set aglow by a phenomenon known as enrosadira. This natural spectacle, which occurs at dawn and dusk, sees the peaks of this UNESCO-listed mountain range turn a beautiful shade of raspberry red as sunlight reacts with minerals in the rocks. It’s a must-see for photographers and nature lovers alike.
Image by Kirsten Frank / Unsplash.com
In Tuscany, swap hiking boots for wine glasses. September calls in the vendemmia (grape harvest) and it’s the perfect time to vineyard-hop your way around the sprawling Chianti hills which are dotted with lush cypress trees and verdant olive groves. Along the way, make a pit stop at the mountainous estate of Castello di Albola, home to some of Tuscany’s highest vineyards. Enjoy a private tour of the estate’s wine cellars and tuck into tasty Tuscan dishes while savouring expertly paired wines. Alternatively, time your visit to coincide with Scansano’s annual Festa dell’Uva (Grape Festival), where the hilltop town celebrates its famed Morellino di Scansano wine.
Image by Malte Jaeger/LAIF-REA
Next on our roundup of reasons to visit Italy in September is fewer crowds in Puglia. One of the country’s most picturesque regions, Puglia stretches down the heel of Italy’s boot. Take advantage of the shoulder season and enjoy the uncrowded Torre dell'Orso Beach, or head slightly further south to Lido Balnearea where you won’t have to compete for a deckchair. Do as the Italians do and embrace dolce far niente (the sweetness of doing nothing). Or, for a change of scenery, weave through the little lanes of Lecce, stopping at trendy terraced cafes, Baroque-style churches and historic palaces – all in the footsteps of a friendly local resident.
Image by Lucy Laucht
Sitting pretty in the heart of the Mediterranean, Sicily in September is a treat. This sunny island (Italy’s largest) holds onto the summer’s warmth, with daytime temperatures climbing as high as 28°C. Stretching over 900 miles, Sicily’s pristine coastline calls for a trip to the beach. Head to Scala dei Turchi to see lunar-like limestone steps rise dramatically from the shore. Venture up the white cliffs for sweeping views of the sparkling sea or admire the natural formations from below with your toes dug into the sand.
For a more secluded spot, visit Calamosche’s cosy cove in the protected Vendicari Nature Reserve in eastern Sicily. Lay your towel on the golden sands and take a dip in the still, warm waters.
Image by Lucy Laucht
Written by Amy Larsen | Header image by flowerz / Fotolia.com
Italy is a holiday hotspot (for good reason), so our help in navigating the crowds is invaluable. From snapping up hard-to-come-by Vatican tickets (at the quietest times of day) to organising an archaeologist to guide you around Pompeii, our consultants have the insider intel to make your trip unforgettable. Stuck on where to stay? Our vetted accommodation options range from family-run ‘trullis’ in Puglia to big-name hotels in Venice. So, whether you're an adventurous family or a couple on a romantic retreat, we can find the version of Italy to suit you.
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