September: 86 places at their best

10 places, each with its window to go.

Hidden Gems of Italy

The Italy Italians take their own vacations in.

Manarola, Cinque Terre
Photo: This Photo was taken by Timothy A. Gonsalves. Feel free to use my photos, but p, CC BY-SA 4.0

The straight answer

Italy's best hidden gems are Matera, Lecce, Ravenna, and Procida: all reachable by train or ferry, all lightly touristed by Italian standards, and all at their best from April to June or in September and October.

The best Italy trip you have not taken yet skips Rome, Florence, and Venice entirely: it is Matera's cave city, Lecce's honey-colored baroque, Ravenna's glittering mosaics, and a pastel fishing harbor on Procida that most Americans have never heard of.

Italy is the rare country where the second tier is not second rate. These are places with UNESCO listings, world-class art, and food towns Italians argue about, and yet you can walk into most of them in June without a reservation made three months out.

Aim for April to June or September to October. The far south, Matera and Tropea especially, bakes in high summer, while spring and early fall give you warm evenings, open trattorias, and piazzas that still belong to the people who live there.

Matera01
Go: Apr-Jun · Sep-Oct

Matera

Matera, Basilicata

A city of cave dwellings carved into a ravine, inhabited for thousands of years and now one of the oldest continuously lived-in settlements on Earth. The Sassi districts are UNESCO-listed, and the 2019 European Capital of Culture title finally gave Matera the infrastructure to match the spectacle.

Hotels →Vrbo rentals →Tours →

materaturismo.it ↗

Lecce02
Go: May-Jun · Sep-Oct

Lecce

Lecce, Puglia

The Florence of the South, carved in soft golden pietra leccese: the facade of Santa Croce is baroque at its most gloriously overboard. Start the morning like a local, with a pasticciotto, the warm custard-filled pastry Lecce invented.

Hotels →Vrbo rentals →Tours →

viaggiareinpuglia.it ↗

Orvieto03
Go: Apr-Jun · Sep-Oct

Orvieto

Orvieto, Umbria

A hill town on a volcanic plug between Rome and Florence with one of Italy's great cathedral facades, all gold mosaic and spires. Descend the Pozzo di San Patrizio, a 16th-century well with double-helix staircases, then surface for a glass of Orvieto Classico.

Hotels →Vrbo rentals →Tours →

umbriatourism.it ↗

Ravenna04
Go: Apr-Jun · Sep-Oct

Ravenna

Ravenna, Emilia-Romagna

Eight UNESCO monuments hold the finest Byzantine mosaics outside Istanbul: the Basilica di San Vitale and the tiny, star-ceilinged Mausoleum of Galla Placidia are jaw-dropping. Dante is buried here, not in Florence, and Ravenna does not let you forget it.

Hotels →Vrbo rentals →Tours →

turismo.ra.it ↗

05Go: May-Jun · Sep

Urbino

Urbino, Marche

A Renaissance city-state preserved almost whole in the hills of the Marche. The Palazzo Ducale houses Piero della Francesca's enigmatic Flagellation, and Raphael's birthplace still stands a few streets uphill.

Hotels →Vrbo rentals →Tours →

vieniaurbino.it ↗

Procida06
Go: May-Jun · Sep

Procida

Procida, Bay of Naples

The Bay of Naples island the ferries skip: no Capri glitz, just the stacked pastel harborfront of Marina Corricella, where Il Postino was filmed. Its 2022 turn as Italian Capital of Culture put it on Italian radar without wrecking it.

Hotels →Vrbo rentals →Tours →

comune.procida.na.it ↗

Bologna07
Go: Apr-Jun · Sep-Oct

Bologna

Bologna, Emilia-Romagna

Hidden in plain sight: Italy's food capital gets a fraction of Florence's visitors. Eat tagliatelle al ragu in the Quadrilatero, then walk the nearly 4-kilometer Portico di San Luca, the longest portico in the world, up to the sanctuary above the city.

Hotels →Vrbo rentals →Tours →

bolognawelcome.com ↗

Mantua08
Go: Apr-Jun · Sep-Oct

Mantua

Mantua, Lombardy

A Renaissance capital ringed by three lakes, UNESCO-listed and strangely empty of foreign visitors. Mantegna's Camera degli Sposi in the Palazzo Ducale and Giulio Romano's frescoed Palazzo Te are two of northern Italy's essential rooms.

Hotels →Vrbo rentals →Tours →

turismo.mantova.it ↗

Ascoli Piceno09
Go: May-Jun · Sep

Ascoli Piceno

Ascoli Piceno, Marche

Piazza del Popolo, paved entirely in polished travertine, is one of Italy's most beautiful squares and almost nobody outside Italy knows it. Order olive all'ascolana, the stuffed fried olives invented here, with an anisette at the Art Nouveau Caffe Meletti.

Hotels →Vrbo rentals →Tours →

visitascoli.it ↗

Tropea10
Go: May-Jun · Sep

Tropea

Tropea, Calabria

An old town stacked on a cliff above white sand and clear Tyrrhenian water, with the sanctuary of Santa Maria dell'Isola on its own rock offshore. Italy crowned it Borgo dei Borghi, the country's most beautiful village, in 2021, and its sweet red onions are famous nationwide.

Hotels →Vrbo rentals →Tours →

calabriastraordinaria.it ↗

Quick answers

When is the best time to go?

April to June or September to October. The northern picks like Mantua and Ravenna are fine all summer, but Matera, Lecce, and Tropea get seriously hot in July and August, and August adds Italian vacation crowds to the beach towns. May, June, and September hit the sweet spot everywhere on this list.

Can I do these without a car?

Mostly yes. Bologna, Ravenna, Mantua, Orvieto, and Lecce are all on the rail network, and Procida is a short ferry from Naples. Matera connects by regional train and bus via Bari, and Urbino, Ascoli Piceno, and Tropea are simply easier with a car, though buses and trains do reach them.

Which ones pair well into one trip?

Three natural clusters: Bologna, Ravenna, and Mantua in the north; Orvieto with Urbino and Ascoli Piceno through Umbria and the Marche; and a southern run of Matera, Lecce, and Tropea, with Procida as the Naples bookend. Each cluster fills a comfortable week.

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