Milan – Recommended Itinerary for a 4-Days Trip
Winter has arrived, and the wind has scattered the clouds of the red states in every direction. The skies are clear, so don’t let a single-digit temperature keep you indoors. If you missed the post on the 10 reasons for a pampering winter vacation in Italy, here’s a reminder. Milan is undoubtedly one of the options you should seriously consider. Take a weekend of 3-4 days to enjoy the northern city, which is the most modern Italy has to offer. A perfect blend of classic Europe with Italian charm.
The abundance of sites and places to visit will allow you to stroll through the charming streets, admire the architecture, sit in one of the trendy cafés just to watch the passersby, and also enter one of the excellent museums in case it rains.
Welcome to Milan – a recommended itinerary for 4 days of travel.
Our first recommendation would be to settle in a hotel in the city center, one that you can walk out of in the morning and return to in the afternoon for a rest, or at the end of the day to collapse onto the bed with all your shopping bags… You have an efficient metro system at your disposal that can shorten distances.
Day 1: Zone 1 of Milan – Centro Storico The Central Area
Castello Sforzesco
The Duomo and Duomo Square
Galleria Vittorio Emanuele
La Scala Square and Theater
Poldi Pezzoli Museum
The ‘Golden Rectangle’ area
If you’re starting, do it right and enter the elegant city like dukes through Castello Sforzesco (in Italian “The Castle of Sforza”). A medieval fortress built in the 15th century by Francesco Sforza, Duke of Milan. Later it was renovated and expanded, and is considered one of the largest and most impressive castles in Europe. After the unification of Italy, it underwent a series of renovations and currently houses some of the city’s museums and art collections.
Milan – Sforza Castle
Via Dante, which exits from the entrance to the castle, is laid out on the medieval route and creates a connection to the Duomo of the city. Via Dante is intended for pedestrians, and besides an initial acquaintance with fashion brands, it often features street performances and will lead you straight to the city center.
Piazza del Duomo (“Cathedral Square”) is the main square of the city. It is named after and dominated by the Milan Cathedral (the Duomo). The square marks the heart of the city, both geographically and due to its artistic, cultural, and social significance. It has a rectangular shape and includes some of the most important buildings in Milan (and in Italy in general). The piazza gradually developed from the 14th century along with the cathedral, which took about 600 years to complete. The square in its current form is thanks to architect Giuseppe Mengoni, from the second half of the 19th century. Aside from the Duomo itself and the Royal Palace, Mengoni’s most prominent addition to the piazza is the Galleria Vittorio Emanuele II, named after the first king of the Kingdom of Italy.
Milan, Piazza Duomo and the impressive cathedral, a Gothic architectural masterpiece
The Cathedral of Milan (Duomo di Milano), stunning in its beauty, is dedicated to the birth of the Blessed Virgin Mary (Santa Maria Nascente), whose golden statue stands atop the cathedral. Construction began in 1386 and finally concluded in 1965. It is the largest church in Italy (St. Peter’s Basilica is larger, located in the Vatican), and the third largest in the world. It contains many works of art, and visiting it (for a fee) is highly recommended.
If you want to experience the visit in a slightly different way, you can go up to the roof (by elevator or stairs) and walk among the sculptures and spires while looking over the square from above. https://www.duomomilano.it/en/ – tickets can be booked in advance on the site.
The Cathedral of Milan
Standing in the square, you will see to your left an entrance to a structure that somewhat resembles a triumphal arch. This is the entrance to Galleria Vittorio Emanuele II, the oldest active shopping gallery in Italy. The building has four levels and is constructed of two intersecting glass and iron arcades that connect Piazza del Duomo to Piazza della Scala. Inside the gallery, there are shops from top Italian fashion houses, as well as cafes and restaurants. On the floor in the center of the gallery, four mosaics depict the emblem of the three capitals of the Kingdom of Italy (Turin, Florence, and Rome) along with Milan. A local tradition states that if you spin three times on your heel on the bull’s testicles in the Turin emblem, it will bring good luck. Why take a chance? Give it a spin.
Milan – Galleria Vittorio Emanuele II
Have you crossed the gallery? You’ve emerged into Piazza della Scala. In the heart of the square stands Leonardo da Vinci pondering, surrounded by four of his students. In front of him is the La Scala opera house, whose exterior does not reflect its interior.
Teatro alla Scala is Milan’s famous opera house, inaugurated in 1778. All the great opera artists of Italy and international singers have performed on its stage. It is regarded as one of the leading opera and ballet theaters in the world. If you manage to include a musical performance in your weekend – you’ve struck gold. If not, near the opera house, the Museum Museo Teatrale alla Scala opened in 1913, based on a large private collection that includes costumes, set designs, scores, paintings, musical instruments, and various props related to theater activities. Additionally, it allows access to the auditorium itself and private viewing boxes.
Milan – La Scala Theater
And now, let’s head toward the “Golden Rectangle” Quadrilatero d’oro, the local name for the street network containing the most famous luxury shopping district in the world. The streets of high fashion. When you have your back to the statue of Leonardo da Vinci and are facing La Scala, turn right onto Via Alessandro Manzoni and take the third turn right onto Via Monte Napoleone. From there, turn left and walk to the end. Wander among trendy boutiques, stylistic showrooms, and extravagant jewelry. Many of the streets are pedestrian-only, making it the perfect place to stroll and admire what money can buy, which is quite a bit. Milan is home to flagship stores of many designers, including Armani, Versace, Prada, and Gucci. All this glamour is concentrated in the Golden Rectangle. The string of recognizable names catches the eye alongside the color and elegance of the shop windows. We don’t mean to stop you, but just to mention that the Golden Rectangle ranks among the most expensive and prestigious areas in the world, alongside Fifth Avenue in New York and the Champs-Élysées in Paris.
Milan – The Golden Rectangle
The Golden Rectangle has more to offer than just shopping. If you feel the need to balance materialism with some culture, among the fashion stores are many historical palaces, including Palazzo Morando Palazzo Morando, which houses the city’s fashion museum, and impressive home museums like Poldi Pezzoli Museo Poldi Pezzoli and Bagatti Valsecchi, Museo Bagatti Valsecchi with impressive art collections.
Enjoy a local break at Pasticceria Cova Pasticceria Cova on Via Monte Napoleone 8, a local institution since 1817 that maintains its high standards to this day.
Looking for a restaurant for dinner?
Here are 3 restaurants, one better than the other, for an amazing culinary experience in Milan:
Buon Appetito
Day 2: Porta Garibaldi – Brera The Modern Area and Brera District
Piazza Gae Aulenti
Corso Como
Eataly Smeraldo
Corso Garibaldi
Brera
In the evening: Navigli Area
As always, we start big. The Piazza Gae Aulenti is the focal point of the most modern neighborhood in Milan and was inaugurated in 2012, dedicated to the renowned architect Gae Aulenti. The buildings surrounding the square are a result of the regeneration of the Garibaldi, Isola, and Varesina neighborhoods, blending historic structures with the modern-designed financial district. The most impressive is the UniCredit Tower, standing at 231 meters, currently the tallest skyscraper in Italy. If you walk through the square towards the circular wooden structure of IBM, you will see on your left the pair of residential towers known as the “Vertical Forest” Bosco Verticale, inaugurated in 2014, which features over 900 trees, conceptualized by architect Stefano Boeri, who collaborated with botanists and gardeners to create a living experience amidst greenery despite the urban location.
Milan – Piazza Gae Aulenti
A pedestrian bridge (recognized by the bronze pipes that look like trumpets) connects Piazza Gae Aulenti to Corso Como. At Corso Como 10, a design complex showcasing and selling works of art, fashion, music, design, and culture, established in 1990 by gallery owner and publisher Carla Sozzani. On the ground floor, alongside the store, there is also an elegant café that certainly invites you to sit and soak in the stylish atmosphere.
Milan – Corso Como 10
Upon exiting the complex, turn left and walk to the end of the street. On your left is the Milanese branch of Eataly, Eataly, a retail chain of high-quality Italian products that includes a variety of restaurants, a bakery, and a cooking school. The chain collaborates with the “Slow Food” movement, which aims to emphasize quality and freshness of food rather than the speed of its preparation, a concept that truly reflects in many Italian restaurants. As you exit Eataly, cross through Piazza Venticinque Aprile and cross the street to Corso Garibaldi.
Milan – Porta Garibaldi
This is one of the most charming streets in the city, perfect for strolling, enjoying window displays, vintage shops, and cafés. Continue wandering along until you reach the intersection with Mercato street. Cross the road and turn left into the first small alley, Via Fiori Chiari, which will lead you into the Brera district located within area 1 (the historic core of the city) concentrated around Via Brera.
The street will widen further ahead and lead you to the Academy of Fine Arts and the Brera Art Gallery, Pinacoteca di Brera, which contributed to Brera’s development as an artist neighborhood and a hub of bohemian atmosphere. Both the academy and the gallery are housed in the historic Palazzo Brera, the main historical building of the area. Within the same building, you’ll also find the botanical garden of Milan, an astronomical observatory, and a national library. You’ll discover not only culture and art here but also an abundance of restaurants, bars, nightclubs, antique shops, and art galleries. Wander through the streets of the district, exploring the small shops and cafés.
As night falls early, you might want to head towards the canal and nightlife area, Navigli. You can easily get there from the Brera district by taking the metro to the Porta Genova station and then walking along Via Valenza until you reach the bridge that leads down to Ripa di Porta Ticinese, filled with bars, restaurants, and clubs. The Navigli is a system of canals interconnected with each other, dug in medieval times for trade purposes and to connect Milan with other nearby cities in a time when there were no roads or trucks, necessitating a swift and convenient route for transporting building materials and goods. Nowadays, they are no longer needed, but part of the system has been preserved, and the former warehouses are now bars and restaurants.
Milan – Navigli District
Day 3: Art, Culture, and Shopping in Milan
“The Last Supper” painting by Leonardo da Vinci near the Church of Santa Maria delle Grazie
The National Museum of Science and Technology
Basilica of Sant’Ambrogio
Shopping (Corso Vittorio Emanuele, Via Torino, Corso Buenos Aires)
In the evening: Just Cavalli Club
Let’s start with Leonardo da Vinci. Although he was not born in Milan, he lived and worked here for about 20 years under the patronage of the Sforza family. You can explore the city following his works, or choose to focus on two or three masterpieces left behind by the Renaissance genius. One of the most famous paintings is a mural in the dining hall of the Convent of Santa Maria delle Grazie known as “The Last Supper” Il Cenacolo. This painting, created at the end of the 15th century, is regarded as one of the most recognized artworks in the Western world. Work on it began around 1495, commissioned as part of a renovation plan for the church and convent by Leonardo’s patron, Ludovico Sforza, Duke of Milan. The painting depicts the moment of the Last Supper of Jesus with his twelve apostles, as told in the New Testament—the moment after Jesus announced that one of his disciples would betray him. Due to the methods used in its creation, many restoration attempts have been made over the years, with the last one completed in 1999. The painting can be viewed in small groups and for a fixed period, and advance booking is required.
Milan – The Last Supper painting by Leonardo da Vinci
Just a 6-minute walk from the convent is the National Museum of Science and Technology named after Leonardo da Vinci Museo Nazionale della Scienza e della Tecnologia Leonardo da Vinci – located at Via San Vittore, 21. The museum is the largest in Italy and dedicated to the genius scientist and artist. It is housed in a former convent and divided into sections based on the topics he worked on, such as: materials, transportation, energy, art, and science.
Another museum related to Da Vinci’s works, which is a bit smaller but visually illustrates his inventions, is located in Piazza della Scala right at the entrance to the Galleria Vittorio Emanuele and is called Leonardo’s World Museum Museo Leonardo3 – Il Mondo di Leonardo.
Still under the culture section:
A visit to the Basilica of Sant’Ambrogio Basilica di Sant’Ambrogio
“If you think the time you live in is bad or unbearable, live well and thus change the time.” December 7th is the feast day of Milan’s patron saint, Saint Ambrose, who was a bishop and theologian and one of the central figures in the city’s Christian history. Known for selflessness and diligence, he is also regarded as a patron of innovative startups today. The ancient church named after him, inaugurated in the 4th century, features impressive Byzantine mosaics and looks very different from the city’s Duomo.
And now, if you please, a bit of shopping:
Exit the church, turn left onto Via Lanzone, and walk until the big intersection where you will turn left onto Via Torino – this is the street where you will find branches of most international chain stores, not necessarily the luxury ones. Sporting goods, electronics, bags, and shoes. If you manage to walk to the end, you will reach the Duomo Square.
If you visited here on the first day, you can treat yourself to a drink on the Terrazza Aperol located just above the entrance to Galleria Vittorio Emanuele on the right, overlooking the Duomo. Treat yourself to an Aperol Spritz, and have an orange day. You can also have hot chocolate if it’s really cold outside.
A cocktail and a more significant snack can be found two buildings down on the rooftop of the Rinascente Department Store at Milano Piazza Duomo – there too, on the food floor, is a terrace with a view of the Duomo Terrazza de La Rinascente.
Milan – La Rinascente terrace
Not into drinks but want a small bite? Right outside the department store, take a left into the alley Via Santa Radegonda, leading you to a place where people are lined up. The first on the right is the line for Luini’s panzerotti, stuffed pastries with sweet or savory fillings – a must-try! Panzerotti Luini.
And across from it Cioccolatitaliani, because what is Italy without gelato?
Head back and turn left along the covered street that will turn into Corso Vittorio Emanuele II, allowing you to complete the shopping experience this time with more familiar international brands. Take your time. Wander into the alleys and stop at one of the cafes. The street ends at a square called Piazza San Babila. From there, slightly right and straight, and you are on Corso Venezia, a broad street that will continue your shopping journey and lead you to a square with a neoclassical structure – Porta Venezia. Beyond the square, Corso Buenos Aires continues, officially recognized as one of the best shopping streets in Milan. What you might call shop till you drop.
And what do you do with all those beautiful clothes we’ve bought? Head to the nightclub Just Cavalli located in Parco Sempione, at the foot of Torre Branca, featuring a restaurant, bar, and dance floor. Founded by fashion designer Roberto Cavalli, who gave it its unique look with animal motifs that are his signature.
Milan – Just Cavalli Club
The restaurant is popular among celebrities, beautiful people, and anyone looking to spend a perfect high-end evening. You can visit the club for an aperitif, dinner, or just for the dance party. Remember that the real action only starts after midnight. The club is managed in conjunction with Discoteca Hollywood, an entertainment icon in Milan for over 20 years.
Day 4: Departing from Milan
This is the recommended itinerary for 3 days of travel in Milan. If you have an extra day in your schedule, depending on your flight, and you feel that you have explored the city enough, and are looking for additional day trip ideas without the need to rent a car, here are 2 day trip options—one to a lakeside city, and one to a charming town—both distinctly beautiful and interesting, accessible from Milan’s central train stations:
