The best cities to visit in Italy in September

With our list of the best cities to visit in Italy in September, you can scratch your last summer-escape itch in style.
The best cities to visit in Italy in September
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A last-gasp summer escape is often necessary when you realise winter is slowly creeping in. At the dusk of another long summer, there is still time for one last adventure, where wearing a T-shirt and going for a swim can slide onto the agenda. There is nothing quite like a cool summer day filled with getting lost in the streets and the buzz of a new city or taking a day trip to explore the surrounding area. 

With our guide to the best cities to visit in Italy in September, you can make the most of these four destinations before hibernation season starts. September is a great time to visit Italy, as the weather is yet to turn fully and the crowds have dissipated from the high season. 

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The are our favourite cities to visit in Italy in September:

Discover the hill towns and villages near Perugia



Perugia, the capital of Umbria, is a historic city that seems to cascade down the hillside. The historical centre, which sits atop the conical hill that this city is draped over, is enwrapped by imposing defensive walls. There is plenty to do and see in Perugia, with medieval architecture exhibited by, and artworks in, Priori Palace. Aside from Perugia's picturesque setting and architecture, the city benefits from an outstanding culinary scene. Whilst understated compared to its neighbour, Tuscany, Umbria has similarly fertile lands, with each season producing different gustatory delights, from truffles to olive oil to wine. Head to the hilltop town of Montefalco to tastes Umbria's ambrosial wines. 

September is a great time to visit Perugia, as the dwindling crowds make meandering the streets easier and the last of the warm weather makes walks between villages and amongst the vines and day trips to other towns more pleasant. Take a trip to the famous hilltop town of Assisi, just a short drive away, to explore the birthplace of Saint Francis and the stunning 13th-century basilica. Perugia is one of the most unassuming destinations to visit on our list of the best cities to visit for a luxury holiday in Italy in September.

Enjoy the last of the warm weather in Naples

Whilst famous for its hearty and delicious pizzas, Naples is a great place to catch the last of the summer, as the crowds begin to recede and the days start to shorten. In September, the weather makes touring far easier and you can still swim in the warm sea or bask in the sun in pursuit of that last-minute tan. Capitalise on a cooler day by climbing the formidable Mount Vesuvius and visiting the fallen, frozen-in-time city of Pompeii. Or take a boat from the Sorrentine Peninsula to the rugged and naturally stunning island of Capri, where the mountain paths beckon for explorers to traverse their lengths. 

One of our favourite things to do whilst visiting Naples is to take a car along the winding and sheer coastal roads of the Amalfi Coast. Start at Positano, where a waterfall of colourful houses cascades down to a pool of bright umbrellas that ripple in the breeze. On this stretch of coast, the only horizontal plane is the lazy Tyrrhenian Sea. Some of the best restaurants are only accessible by boat, where you can laze beside the sea and indulge in fresh fish and limoncello.

Discover Florence: Food, wine and history


Florence is known for its sheer natural beauty; a city bursting with sensory delights, whether the smell of Tuscan cuisine dancing down the street on a light breeze, or the sight of the imposing cathedral's roof burning brightly in the midday sun. In the city's famous galleries, you'll find prominent works from the middle ages to the modern period, including Michelangelo's David and Botticelli's Birth of Venus. 

September's weather is conducive to a mesmeric break in Florence, with plenty of sunshine but fewer scorching days. Saunter the streets with a refreshing ice cream in hand, racing the melting cream to the bottom of the cone, before enjoying a Florentine special in the evening: a Negroni. Dinner comes easily for all predilections in Florence: street food is bounteous and plenty of fine-dining restaurants can be found, either discretely tucked into quiet streets or commanding breathtaking views of the city. One of our favourite restaurants is Michelin-starred Borgo San Jacopo, from where you can admire the warmly lit Ponte Vecchio over the best of Tuscany's flavours. Florence is easily on the top of our list of the best cities to visit in Italy in September. 

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Explore the fishing villages around Bari



Italy's heel is home to swathes of sun-soaked beaches, where small fishing villages and towns are perched on cliffs at the fringes of the Adriatic. From Bari, with its labyrinthine old town and 11th-century basilica, there are plenty of magical port and hill towns to explore, as well as beaches to cool off on during September's warmer days. Bari is one of the best cities to visit in Italy in September for great day trips to picture-perfect areas.

Polignano a Mare is one of the most picturesque towns. Its iconic beach, Lama Monachile, is cradled by the town and the protection afforded by the two cliffs crested with white-washed houses makes the water transparent. Here, the sea lazily lurches towards the roman bridge at the top of the beach. Another paradisaical, almost fairytale-like, village lies further inland from the small port town of Monopoli. Alberobello's narrow cobbled streets are flanked by round buildings with conical roofs; their whitewashed facades resemble fallen ice creams. You can also head north from Bari, towards Vieste, which is set in the Gargano National Park. The town is perched on a promontory, beneath which the emerald waters of the Adriatic entice you for a cooling dip. In the park, the limestone cliffs have eroded into doorways and windows that jut from the flat surface of the sea. 

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With Le Collectionist, you can explore Italy - one of our favourite luxury holiday destinations - this September with ease. Simply start by browsing our collection of luxury villa rentals in Italy to find your dream holiday home.

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