The Ultimate Itinerary for a Weekend in Milan

All the best historic, cultural and food spots for a long weekend in Italy.

Milan is famous for being one of the main fashion capitals of the world, but it also has a rich history, a delicious food-scene and interesting culture. With all the attractions of a large city, it is relatively well compact, making it the perfect destination for a long-weekend. I’ve put together my perfect itinerary for 2 days in Milan, with additional suggestions for longer stays.

Day 1 – Central and Northern parts of the city 

For your first day in Milan I would recommend checking off the main attractions of the city, including the Duomo cathedral and Castello Sforzesco. These attractions are all towards the central and northern parts of the city, and don’t involve much walking between them. 

Duomo di Milano 

Bit of trivia for you: where is the biggest church in the Italian Republic? Your first thought may jump to St Peter’s Basilica in the Vatican City. The correct answer is in fact the Duomo di Milano. Dating back to 1386, this magnificent cathedral took nearly six centuries to construct and is the focal point of the city. 

The best way to truly appreciate the detailed spires and over 3,000 statues is from the rooftop. For €16,50, you’ll be able to climb the 250 stairs for a close up look at the roof’s gothic architecture and a bird’s-eye view of the city below. This ticket also gains you access to the inside of the cathedral to complete your visit of this architectural wonder. Whilst you can buy tickets to just visit the roof or the cathedral, both are worth seeing, and it won’t save you much money just doing one or the other. Also, make sure you purchase your tickets in advance online – this will save you from a painfully long queue during peak months.

Galleria Vittorio Emanuele II 

Undeniably, the most photogenic shopping centre you will ever visit, the Galleria Vittorio Emanuele II is just steps away from the Duomo and houses some of the most exclusive boutiques and luxury stores in the city. Famed for its glass dome ceiling and intrinsic mosaic floor, this site is very popular with tourists – so arrive early if you want to avoid the crowds. 

Castello Sforzesco

Built between 1300 and 1400, the Castello Sforzesco is one of the biggest castles in Europe. Back in its heyday, you would have struggled to get inside this impenetrable fortress with its impressive defensive walls, but now visitors are welcomed with open arms to enjoy the historic courtyards and grounds for free. Today, the castle is also home to seven specialist museums, which together champion some of the best examples of the city’s cultural history. You can purchase tickets on the day (€5,00), or enjoy free entry on every first Sunday of the month, and from 2pm every first and third Tuesday.

Parco Sempione

Escape the busy streets of the city and relax in the Parco Sempione; situated just beside the Castello Sforzesco. The park is home to many species of birds, and even some terrapin in the lake! Bring a picnic or simply pass through on your way down to the Arco Della Pace. 

Arco Della Pace 

It’s impossible to miss the 25m-high arches of this famous Milan monument when you are in the north of the city. The Arco Della Pace, translated as the Arch of Peace, mirrors the Arc de Triomphe in Paris. It marks the start of the main road which connects Milan to the French capital. 

Food and Drink for Day 1 (central/north of city)

Osteria da Fortunata Restaurant 

We had a lovely dinner at this restaurant, located just a couple of streets away from the castle. Here I tried some of the best pasta I have ever eaten – but it is very popular with tourists so be prepared to wait for a table. The best tables are situated by the window looking into the kitchen, where you can watch the dough be transformed into fresh pasta right in front of you! If the queue is too long, don’t fret – along the neighbouring cobbled streets are plenty of other restaurants to choose from. 

Terrazza Aperol (if inclined)

When visiting the Piazza Del Duomo you can’t miss the bright orange umbrellas from the Aperol Terrance. Channel you’re inner influencer and shell out a small fortune (€18, eek) for a cocktail and fancy apperitivos. Whilst the drinks and appetisers are delicious, you are paying a premium for the location and brand name. Also, be prepared to queue for a table and pay to use the bathroom. 

Jazz Cafe Milano 

If you are looking for a splurge for the holiday, why not consider a dinner show at the Jazz Cafe Milano? This lively restaurant-bar, has frequent live acts and DJs, and is a favourite amongst locals. Around midnight the whole restaurant becomes a dance floor, and you can enjoy some Italian music as well as international hits. We seemed to be one of the only tourists, but felt extremely welcome. 


Slice is a great cheap option if you are looking for some tasty take-away style pizza. They are very generous with their toppings, all of which are prepared fresh, including the slices of ham! It is also one of the only food outlets open until 3am Thurs-Sun nights.

Day 2 – Southern part of the city  

For your second day in Milan, make your way towards the southern part of the city, where you can find the picturesque canal district, historic churches and many cool bars. You won’t be too far from the city centre but if you fancied an alternative to walking why don’t you take an…

Old-fashioned Tram Ride

Milan is a relatively compact city and easy to navigate by foot. However, a great way to experience some of the city’s history is to step back in time and take a ride on the old-fashioned trams. Milan’s tram network spans back nearly 150 years, when they were originally pulled by horses. You can purchase several one-way tickets or a 24hr/48hr ticket from metro stations, kiosks or off-licenses.  

Basilicia Di San Lorenzo

Situated just 5 mins from the Canal district, the Basilicia Di San Lorenzo is one of the oldest churches in Italy, dating back to the forth century! As you approach through the square, you will even pass third century roman ruins. Inside you can admire the impressive marble stonework and decorative mosaic flooring, and unlike the Duomo, it is free to enter. 

Explore the Canal district

Towards the south-west of the city, you will find the beautiful canal district – brimming with atmospheric bars and alfresco dining. Historically, the entire city was connected with canals – similar to Venice, but today a few remain making up the Navigli neighbourhood. Visit during the day and you can enjoy a picturesque and peaceful stroll along the canals, or visit in the evenings for it’s lively nightlife and romantic string lights. In the surrounding areas you’ll find lots of trendy stores and street art, and may even bag yourself a vintage bargain at one of the flea markets. 

Food and Drink Day 2 – South of City 


Signorvino is a lovely resonantly-priced bar on the intersection between two of the canals. Here we enjoyed a crisp bottle of Prosecco and a selection of aperitivos. 

Vetusta Insigna 

Along the canals we also stopped by Vetusta Insigna for a late lunch, which was full of character and charm. I had some of the best gnocchi I have ever tasted here, although it did come with a more “laid back” Italian style service! 

Staying longer than a weekend? Visit Lake Como 

The North of Italy harbours some of the most beautiful mountain and lake landscapes I have visited. If you have time and the sun is shining, Lake Como is only a 38 minute direct train journey away, with tickets starting from €4.80.