No Milan travel itinerary for newcomers is complete without a stop to marvel at the city’s show-stopping Duomo. It took six centuries to complete this colossal masterpiece of Gothic architecture, so plan to spend at least an hour enjoying the marble-clad facade, soaring interiors, and panoramic roof terrace. Most Milan walking tours include a stop inside the church, or you can visit on your own. Just remember to book tickets for this popular attraction in advance.

Milan is home to Leonardo da Vinci’s landmark Last Supper painting, which decorates the refectory wall inside the monastery adjacent to the Church of Santa Maria delle Grazie (Chiesa di Santa Maria delle Grazie). Visitors are only allowed to view the painting in 15-minute time slots and it gets very crowded, so consider booking a skip-the-line tour so you’ll have plenty of time afterward to visit the neighboring church and admire its mix of Gothic and Renaissance architecture.

Countless legends have graced the stage of La Scala Opera House (Teatro alla Scala), known affectionately as La Scala. You can view the understated exterior on a hop-on-hop-off bus tour or self-guided audio tour of the city, but to admire the lavish gilded-and-velvet interiors, you’ll have to visit with a guide as part of a La Scala theater and museum tour. Alternatively, book tickets to attend a performance of opera, ballet, or classical music concert.

A stroll beneath the soaring glass ceilings of the Galleria Vittorio Emanuele II is one of the essential experiences in Milan for first timers, and most city sightseeing tours include a stop here to admire its Renaissance Revival architecture. It’s easy to fit this 19th-century shopping center into a Milan travel itinerary for newcomers as it sits directly between the Duomo and La Scala, and you can meander your way between the high-end boutiques and historic cafés that fill its double arcades.

There are several areas to focus on during a shopping tour of Milan, from the trendy thoroughfares of Corso Vittorio Emanuele II and Corso Buenos Aires to the Quadrilatero d’Oro, or Golden Rectangle, where the lion’s share of the city’s haute couture boutiques are clustered. Lovers of interior design can find one-of-a-kind décor in the Brera district, while vintage enthusiasts can unearth treasures in the tiny shops in Navigli, the city’s canal quarter.

It’s no surprise that this chic city is home to a buzzy nightlife scene, and an aperitivo break in the trendy Navigli neighborhood is one of the top things to do in Milan for beginners. Once the sun begins to set, make a beeline for the bars that line the historic canals and sip a classic Italian cocktail, or join a local insider for an aperitivo and street food tour to discover the best spots for bites and sips.

The austere Sforza Castle (Castello Sforzesco) lives in the middle of the modern metropolis, a surprising sight when exploring Milan as a first-time tourist. However, the 15th-century fortress is one of the most important historic stops in the city. Explore its sprawling interiors and visit a few of its resident museums, archives, and libraries, like the Museo Pietà Rondanini, home to Michelangelo’s last unfinished work, which is the most famous.

Step away from the city's bustle and traffic for a cultural tour of the charming Brera neighborhood. This largely pedestrian area in the heart of Milan is known for its historic townhouses, high-end shops, and fashionable eateries, but it’s also home to the Brera Art Gallery (Pinacoteca di Brera) and Brera Botanical Garden. Meander through the district on your own or with a private tour for personalized insights into Brera’s history and landmarks.

One of the most unexpected Milan travel tips for newcomers is to use the city as a base for day trips to explore the nearby attractions. Lake Como, Lake Maggiore, and Lake Orta are ideal for an excursion, and the Alps lie just beyond. Join a Lake Como and Bellagio day trip from Milan, or opt to explore Lake Maggiore or Lake Orta on your own—both have fewer crowds than their A-list neighbor.

Milan may not be a wine destination, but the Piedmont wine country southwest of the city is the birthplace of Italian wines from Barolo to Barbaresco. Take a break from the urban bustle to explore the UNESCO–listed hills of Langhe-Roero and Monferrato with a wine tour from Milan. Or, visit boutique cellars to sip bold reds while enjoying views over the picturesque vineyard-covered hillsides, stopping to visit villages like Alba and sample the region’s legendary cuisine.