1. Attend an opera at Verona Arena

Set in the evocative Arena — an Ancient Roman amphitheater that dates back to 30 AD — the annual Verona Opera Festival is one of the most revered music events in the country. From June to September each year, this already impressive amphitheater is transformed into a magnificent open-air opera venue unlike any else in the world. The origins of the festival date back to the early twentieth century when the heavenly acoustics of the arena were first discovered.

The festival was officially inaugurated in 1913 with Giuseppe Verdi’s Aida, an opera that continues to have a special connection with the festival. Thanks to the Arena’s breadth and majesty, the venue lends itself to one-of-a-kind performances of monumental operas, meaning Aida often appears on the festival’s lineup together with other grand operas, such as Turandot, Tosca, and Nabucco. Over the years, the festival has hosted performances by the biggest names in opera including Maria Callas, Luciano Pavarotti, and Plácido Domingo. For fans of opera, music, and live performances in general, an evening at the Arena with a group of friends is a once-in-a-lifetime event.

In addition to the opera festival, visitors to Verona have plenty more to explore. The city itself is renowned for its iconic cultural sights including Piazza Bra, Piazza delle Erbe, and Castelvecchio. As the hometown of Romeo and Juliet, couples will delight in the romantic atmosphere of Verona while visiting Juliet’s balcony or sharing an aperitivo at a local outdoor café during twilight.

What’s more, Verona is well-positioned with easy access to other highlights of the Veneto region including the vibrant city of Venice, the tranquil shores of Lake Garda (Italy’s largest lake), and the picturesque Valpolicella wine region. During a trip to Verona, the hardest part will be deciding what to see next with your friends.

2. Enjoy wine tasting with dinner under the stars at a countryside wineyard in Tuscany

Picture a scenic drive through Tuscany’s iconic landscapes as the late afternoon sun shines over rolling hills and cypress trees. Admire the rich scenery and historic vineyards before arriving at an estate in one of Tuscany’s renowned wine areas, such as Chianti or Val d’Orcia.

Breathe in the tranquility of the countryside as you explore the grounds. Then, when the warm air gives way to cooler temperatures, share a wine tasting aperitivo with your party of friends just before sunset. Surrounded by the spectacular beauty of the Tuscan countryside, you’ll learn about the winemaking traditions passed down from generation to generation that have shaped the area’s most renowned wines.

As the sun descends over the horizon, enjoy a dinner among the best of friends surrounded by the vineyards of the wine estate. Savor the flavors of Tuscany’s legendary cuisine and the freshness of locally-grown seasonal ingredients. This intimate dinner under the stars is the perfect opportunity to spend quality time with good company. By the end of your evening, you could even add wine connoisseur to your list of accomplishments.

Whether you prefer to stay deep in the heart of the Tuscan countryside, or in the cities of Florence or Siena, surrounded by a wealth of art, history, and incomparable architecture, you and your friends can live the Tuscan countryside experience of your dreams.

3. Visit Sicily during the colorful Caltagirone Infiorata and evocative Feast of San Giacomo

The charming town of Caltagirone located on the island of Sicily may be small, but it hosts two of the region’s most fascinating cultural events. Caltagirone is best known for its ceramic art and the famous Scalinata di Santa Maria del Monte, a staircase composed of 142 steps, each decorated with hand-painted maiolica tiles. The staircase, which spans just over 425 feet, dates back to the seventeenth century and was built to connect the newer and older parts of the town. Though this unique town is well worth a visit any time of year, it truly comes alive during two immersive folkloric events.

If you and your friends travel to Caltagirone in May, you’ll be graced with the beauty of the Infiorata. The event, which typically extends from April 25 to June 2, is held in honor of the Madonna of Conadomini. Just before the Infiorata begins, locals carefully place vases of colorful flowers along the steps of the Scalinata to create intricate images and motifs that differ each year.

During the Infiorata, visitors can attend other events as well, such as music performances and pottery workshops. The locals also host a procession through the historic center of town complete with period costumes, colorful carts, and gifts for the Virgin Mary that are brought up to the Church of Santa Maria del Monte at the top of the steps.

As if the beauty of the Infiorata weren’t enough, Caltagirone’s other main religious feast is also a sight to be seen. On July 24 and July 25, the town’s staircase takes centerstage once more during the Feast of San Giacomo, Caltagirone’s patron saint. This time, thousands of colorful candles are placed on the steps to create an elaborate, illuminated image. In addition to the light display, called Illuminata, the locals celebrate with music, fireworks, and a procession through town.

Even if travelers aren’t religious or devout Christians, the events can provide a unique opportunity to live completely authentic and local experiences that are part of Sicilian culture. Outside of these events, Caltagirone amazes with its historic city center as well as the Norman Baroque Cathedral of San Giuliano, ceramic traditions, streets lined with artisan workshops, and archeological sites…then there’s still the rest of Sicily to explore!

4. Participate in a cooking class at a typical Masseria in Apulia

Travel to the picturesque heel of Italy where time stands still and historic traditions are very much alive. As far as coastal destinations go, the region of Puglia seems to have it all: a long, rich history that began with the Mycenaean Greeks, dramatic cliffside towns suspended over brilliant blue water, tranquil countryside landscapes, iconic architecture, and, of course, one of the most distinct regional cuisines in all of Italy.

Venture into this legendary countryside with your friends to visit a rustic stone masseria (a traditional farmhouse native to Puglia) surrounded by centuries-old olive trees and coastal panoramas on the horizon. After taking in the atmosphere, you and your friends will begin a cooking class in the authentic setting of the masseria.

Follow along as a local culinary expert, such as a professional chef or a native grandma sharing her ancestors’ recipes, shows you how to prepare traditional dishes just as they were made in the past. With a culinary tradition as rich as Puglia’s, there are countless local dishes including handmade pasta, such as the typical orecchiette (a symbol of Puglia), as well as crunchy taralli crackers, divine fried panzerotti filled with tomato and mozzarella, or local focaccia flatbread topped with tomatoes.

No matter what delicious local specialty you learn to cook, after creating your culinary masterpieces you’ll share an unforgettable meal with your friends under the olive trees or another special corner of the masseria featuring the remarkable flavors of Puglia’s cuisine paired with locally produced wine. You’ll also have the chance to taste Puglia’s extra virgin olive oil, which is considered to be among the highest quality olive oils produced in Italy.

In addition to learning the secrets of Puglia’s cuisine, this remarkable region has plenty more to explore from the famous Trulli dwellings in Alberobello and the rest of the Itria Valley to the beautiful Baroque architecture of Lecce and the whitewashed skyline of Ostuni. Then, of course, there are also the region’s natural wonders, such as the Castellana Caves, and the inimitable charm of small coastal towns, such as Polignano a Mare. No matter how you choose to spend your time, you won’t regret a visit to sunny Puglia with your dearest friends.

5. Share a private dinner at Villa del Balbianello in Lake Como

For an extravagant and unparalleled experience to share with your closest friends, look no further than the shores of Lake Como in Northern Italy. This picturesque lake is dotted with stately villas and expansive gardens. Among these, the gorgeous Villa del Balbianello is particularly renowned for its elegance. Villa del Balbianello’s location at the tip of a small peninsula makes it even more remarkable as the property, its gardens, and terraces are surrounded by water with stunning panoramas from every angle. Today, the villa is a museum that can be toured, and it can also be reserved for private events.

Imagine spending a few hours with your friends exploring Lake Como on a private luxury boat. Feel like the real jet set as you admire important historic villas and take in the most impressive views around the lake directly from the water. Afterwards, make your grand entrance by arriving at Villa del Balbianello’s dock in your private boat to begin the evening in style.

Within the luxurious setting of Villa del Balbianello, you’ll sit down for your private dinner party surrounded by rich collections of paintings, sculptures, and lavishly decorated rooms with period furniture. Feast on Lake Como’s refined local specialties consisting of fresh and flavorful ingredients. Admire incomparable views of the lake from the terraces of the villa and take an after-dinner stroll through the lush gardens. A private dinner with the best of company and particularly in this setting overlooking the lake will feel almost like a modern-day fairy tale.

Moreover, as the third largest lake in Italy, Lake Como still offers so much more to see. A trip to this area of the lake makes it ideal to explore other pearls, such as Villa Carlotta in Tremezzo as well as the historic city of Como, glamorous Bellagio, and tranquil Varenna.

The area’s natural beauty has also made it an idyllic shooting location for several films over the years. Villa del Balbianello’s exquisite scenery in particular has been featured in films such as A Month by the Lake (1995), Star War Episode II: Attack of the Clones (2002), and Casino Royale (2006). More recently, in March 2021, Hollywood stars including Lady Gaga, Adam Driver, Al Pacino, Jeremy Irons, and Jared Leto were steps away from Villa del Balbianello to shoot scenes for the upcoming film House of Gucci directed by Ridley Scott. And, of course, George Clooney’s summer residence is nearby, meaning that A-list celebrity sightings are possible as the American actor often invites famous friends to his villa.