Two-Week Italy Itinerary: 6 Essential Stops

Where design meets decadence, Milan is a stylish introduction to Italy. With its neoclassical grandeur, high-end shopping arcades and iconic art, the city is an elegant blend of old and new.

EXPLORE

Casa Cipriani Milano is New York elegance with a Milanese soul. Set within the iconic Palazzo Bernasconi at the corner of Corso Venezia and Via Palestro, this boutique hotel channels the charm of a private members’ club. With just 15 rooms and suites designed by Florentine architect Michele Bonan, renowned for his eye for detail and sartorial flair, you’re mere steps from Milan’s cultural pulse, yet blissfully cocooned in serenity.

Just two hours east of Milan lies Lake Garda, where rolling hills and glacial waters set the scene for lakeside lazing.

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• Wander the cobbled streets of nearby storybook village of Malcesine or take the cable car up Monte Baldo for sweeping views of the lake and Italian Alps.
• Visit Sirmione’s Grotte di Catullo, ancient Roman ruins perched dramatically on a peninsula, then take a dip in the nearby thermal springs.
• Cruise across the lake by ferry, hopping between charming lakeside towns like Limone sul Garda, Riva del Garda and Bardolino.
• Hike or bike the Strada della Forra, a winding gorge road dubbed one of the most beautiful drives in the world.
• Go wine tasting in the Valpolicella region, just inland, known for its Amarone and scenic vineyard-dotted hills.

Tucked into a tranquil bay on Lake Garda’s Verona side, Val di Sogno is an adults-only escape that feels both intimate and indulgent. With just 35 design-forward rooms, a heated lakeside pool and al fresco dining surrounded by olive trees, this boutique gem offers serenity in every detail—plus an intimate spa experience perfect for unplugging.

Drive three hours south to the birthplace of the Renaissance. Florence is a feast for the eyes—and the appetite.

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• Book timed entry to see Michelangelo’s David at Accademia Gallery or Botticelli’s The Birth of Venus at the Uffizi Gallery.
• Marvel at the Cathedral of Santa Maria del Fiore—also known as the Duomo Di Firenze—with its striking red dome by Filippo Brunelleschi. Climb to the top for breathtaking city views.
• Watch the sunset from Piazzale Michelangelo.
• Cross the Ponte Vecchio for jewelry shopping with a view.
• Sample truffle pasta at trattorias like Il Santo Bevitore and Osteria delle Tre Panche.
• If time allows, detour into the Tuscan countryside for a quick Chianti tasting.

Brunelleschi Hotel blends history and luxury inside Florence’s oldest building, the Torre della Pagliazza—a restored medieval church and Byzantine tower. Steps from the Duomo and top gelaterias, it’s an elegant retreat in the heart of the city. Don’t miss dinner at the on-site Santa Elisabetta, a two Michelin star gem tucked within the tower’s ancient walls.

All roads lead to Rome—and for good reason. Ancient ruins, vibrant piazza and trattorias tucked into cobblestone alleys make every moment cinematic.

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• Tour the Colosseum and Roman Forum in the early morning light.
• Toss a coin into the Trevi Fountain, then grab espresso nearby.
• Visit the Pantheon and Vatican City, including St. Peter’s Basilica and the Sistine Chapel.
• Have a twilight stroll through Trastevere followed by dinner at Roscioli.
• For the sweet tooth: seek out maritozzi or gelato from Gelateria del Teatro.

Once a palace for ambassadors, now a Belle Époque beauty reborn, InterContinental Rome Ambasciatori Palace pairs timeless grandeur with modern luxury on glamorous Via Veneto. Sip rooftop cocktails with sweeping city views, then step out to explore nearby icons like the Spanish Steps. Inside, marble staircases and bespoke art recall the building’s stately past.

Roughly three hours from Rome, it’s best to arrive in Positano by private transfer, letting someone else handle the hairpin turns of the Amalfi Coast as you descend into this cliffside village where pastel buildings tumble toward the sea and the air smells faintly of lemons and sea spray.

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• Wander Positano’s narrow lanes and pop into boutiques for handmade sandals and linen.
• Lounge on Spiaggia Grande with a spritz in hand.
• Book dinner well in advance at La Sponda at Le Sirenuse for a candlelit cliffside experience.
• Discover more hidden gems and local favorites in our Amalfi Coast Destination Guide.

Perched above Positano with cinematic views, Villa Treville is an Amalfi Coast escape steeped in old-world glamour. Once home to director Franco Zeffirelli, this cliffside estate now welcomes guests (including the likes of Madonna and Jennifer Lopez) to its lush gardens, breezy terrace and artfully restored villas. Dine al fresco at Maestro’s, plunge into the sea from a private beach and soak up the magic of the Mediterranean.

Just one hour away, end your journey in sun-drenched Sorrento, a clifftop town that serves as a perfect base to explore the Bay of Naples and beyond.

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• Wander the historic center for limoncello tastings and panoramic piazzas.
• Yacht over to Capri for a Blue Grotto visit or lunch at La Fontelina.
• Ferry to Naples for a pizza pilgrimage.
• Visit the ruins of Pompeii, a short drive away.
• Toast to your Italian adventure with a seafood dinner overlooking Mount Vesuvius.

Suspended above the Bay of Naples with views stretching to Mount Vesuvius, Mediterraneo Sorrento is a clifftop sanctuary that fuses timeless charm with Mediterranean tones. Savor seafood and sunsets at Vista Sky Bar, wander the citrus-scented gardens or unwind in breezy, blue-and-white rooms designed to echo the sea. It’s the kind of place where every hour feels golden.