Enchanting itineraries for an Italian summer

Italy has it all. Beautiful cities layered with history at every turn. Rolling landscapes straight out of a Renaissance painting. World-famous food and wine that tells the story of each unique region. Glamorous coastal towns and museums filled with masterpieces. Sun-baked islands and lush mountains. You could plan a thousand trips to Italy and always discover something new, and although the country is a perennial favorite of travelers, it’s still possible to find authentic, under-the-radar experiences—especially when you tap into the intel and connections of Italian-owned hotels. With some of the country’s best-loved hoteliers as your guides, here’s how to plan your next Italian summer.

While the gleaming Rialto Bridge and the Gothic drama of the Doge’s Palace may be the image of Venice in thousands of paintings and photographs, there’s nothing quite as romantic as getting lost in the labyrinthine backstreets and bridges of the floating city’s quieter quarters or taking a sunset stroll along the Zattere. Spread across 118 islands, Venice attracts millions of travelers each year—but it’s easy to shake them off. Start by choosing a hotel away from the crowds, such as Ca’ di Dio on the city’s still-authentic eastern side.

In fair Verona, just over an hour away by train, couples come to walk in the footsteps of star-crossed lovers Romeo and Juliet. The balcony at Casa di Giulietta is a classic stop—a short amble from the ornate Due Torri Hotel—but more charming still is to wander hand in hand around the glorious Giardino Giusti, or to catch the summer’s open-air opera festival at the Roman amphitheater.

From the Romans to the Renaissance, Italy has shaped culture for millennia. All roads, as ever, lead to Rome, which today is an open-air museum on the grandest stage, with its ancient ruins, Baroque churches and sculpture-studded fountains. The Galleria Borghese is unmissable for its heart-stopping Caravaggios, but for something more sharply contemporary, add the modern art of the MAXXI to your cultural agenda. Hotels here are works of art in themselves, such as the Art Deco palazzo of Baglioni Hotel Regina, or the more contemporary DoubleTree by Hilton Rome Monti.

Continue the arty adventure in Florence, where Michelangelo sculpted David (now in the Accademia) and Botticelli painted The Birth of Venus (hanging in the Uffizi). Florence’s wonders aren’t just found in its two most famous galleries: Palazzo Strozzi platforms boundary-pushing artists like Tracey Emin, while the tiny Cappella dei Magi is a marvel, almost entirely covered in frescoes by Benozzo Gozzoli. Make like a Renaissance benefactor and stay at the upscale Art Hotel Villa Agape, surveying the city from the Florentine hills.

The largest island in the Mediterranean, Sicily has been at the crossroads of civilizations—Greek, Roma, Arab, Norman, Phoenician—who each left their mark beneath the brooding Mount Etna. The most delicious way to get the flavor of this cultural melting pot is through Sicily’s food. Start on the streets of its charismatic capital Palermo, sampling arancini (fried risotto balls), cannoli (tubes of crisp pastry with a sweet ricotta filling), panelle (fritters made with chickpea flour), or even pani câ meusa for the brave (that’s a spleen sandwich).

The Greeks also left their architectural mark—see the most spectacular examples at the Valley of the Temples outside Agrigento, then worship the gods of sun and sea at Mangia’s Torre del Barone Resort & Spa just along the coast. The latest devoted pilgrims, however, come set-jetting in search of Sicily’s stardust. Channel your own A-list style from the infinity pool of UNA HOTELS Capotaormina.

Milan’s powerhouse role in fashion is evident throughout the city, from the stylish shoppers along the cobblestone streets of the Brera district to the boutique-lined Via Montenapoleone. You can’t miss the mega Fondazione Prada art complex (stop for an espresso at the Wes Anderson-designed Bar Luce) or the Prada-owned pasticcerie Marchesi 1824 dotted around town. Aperitivo hour is the best time for people-watching, preferably with a negroni sbagliato (prosecco, Campari, vermouth) at the iconic Bar Basso. Sleek hotel Palazzo Viridis is perfectly placed between the central big-hitters and up-and-coming neighborhoods to dip in and out of the action.

On sunny weekends, the scene migrates to the shores of Lake Como where the calm waters sparkle and many of the neoclassical lakeside villas have been turned into majestic hotels, such as the Grand Hotel Victoria on the quieter western side. Wander the pretty pastel towns of Menaggio and Tremezzina, take to the water in a glossy wooden Riva, or simply soak up its splendor from the terrace.