Italy in summer is a feast — for the eyes, the ears, the palate, and the spirit. As the country shakes off spring and steps into its sun-drenched season, piazzas come alive with music, lanterns float through ancient streets, and entire towns gather to celebrate what Italians do best: wine, tradition, art, and good food. Here, we round up 10 can’t-miss events that go beyond the typical tourist fare — think barrel-rolling contests in Montepulciano and opera in Roman amphitheaters. It’s time to plan your most delicious, dramatic, and dazzling Italian summer yet. Your home base? The Club’s two two-bedroom Florence apartments — perfectly positioned for festival-hopping across Tuscany and beyond.

For the Curtain Call Connoisseur

Opera under the stars and world-class jazz performances — because music always sounds better in Italy.

Arena di Verona Opera Festival: June 13 – September 6

Set in a first-century Roman amphitheater, this iconic summer opera festival draws music lovers from around the globe to Verona’s open-air arena. The program is a sweeping blend of classics — Verdi, Puccini, and Bizet among them — performed under the stars with the kind of grand, theatrical flair that only Italy can deliver. It’s dramatic, unforgettable, and undeniably bucket-list worthy.

Florence Jazz Festival: September 4 – 15

Over a dozen venues scattered across Florence — from historic palazzi to tucked-away gardens — host some of the best jazz acts Europe has to offer. It’s a sultry, improvisational backdrop to your evenings in Tuscany, with free street performances and exclusive ticketed events alike. Think saxophones echoing through Renaissance courtyards and nightcaps with a side of swing.

For the Oenophile with a Passport

Barrel-rolling contests, Chianti tastings, and vineyard-to-table celebrations.

Goblets of Stars: July 27 – August 10

Spanning wine towns from Piedmont to Puglia, this nationwide celebration pairs stargazing with tastings from top local producers. Expect candlelit vineyard dinners, live music, and winemakers pouring their best under August’s Perseid meteor showers. It’s less of a festival and more of a wine-soaked love letter to Italian summer nights.

Expo Chianti Classico: September 11 – 14

Held in Greve in Chianti, the birthplace of Italy’s most beloved red, this four-day event celebrates all things Chianti Classico. Sample hundreds of wines, stroll through food markets, meet producers, and brush up on your DOCG knowledge. Bonus: the town square turns into a wine-tasting playground, and yes, it’s as magical as it sounds.

Grape Festival, Impruneta: September 28

One of Tuscany’s most colorful harvest festivals, this one-day event is a full-on spectacle complete with elaborate floats, grape-themed performances, and parades that turn vino into performance art. It’s community theater meets wine pageantry — and somehow, it works beautifully.

For the Cheese-Obsessed & Culturally Curious

Artisan pecorino, ancient rituals, and lanterns lighting the night sky.

Pecorino Cheese Festival: September 7

Pienza is already known for its pecorino, but during this annual festival, the entire town turns into a cheese-lover’s paradise. Expect tasting stations, cheese-rolling competitions (yes, really), and artisan stalls dotting the cobblestone streets. Come hungry, leave with a suitcase full of aged wedges.

Festival of the Paper Lanterns: September 7

A luminous tradition dating back to the 1600s, this Florence favorite sees children and adults alike parading through the historic center with handcrafted lanterns in every shape imaginable. Add in street performers, music, and a sense of collective nostalgia, and it’s pure Italian magic.

Feast of San Lorenzo: August 10

Locals flock to the San Lorenzo neighborhood for this annual celebration, which honors the patron saint of the poor with free food, communal tables, outdoor concerts, and fireworks over the Arno. It's equal parts spiritual, festive, and delicious.

For the Thrill-Seeker with a Love of Tradition

Historic races and high-stakes competition through medieval streets.

Palio dell’Assunta: August 16

Italy’s most famous horse race is pure theater. Ten riders, each representing a district of Siena, race bareback around Piazza del Campo in a whirlwind 90 seconds that’s as emotional as it is exhilarating. It’s preceded by days of pageantry, parades, and neighborhood pride. Pro tip: secure your spot early.

Bravìo of the Barrels (Montepulciano): August 31

In Montepulciano, wine isn’t just for sipping — it’s a full-contact sport. During the Bravìo delle Botti, local teams charge up the town’s steep, cobblestone streets, pushing 80-kilo wine barrels in a centuries-old contest of muscle, pride, and pageantry. Equal parts athletic feat and festive tradition, the real celebration begins when the race ends.