Lisbon and Milan both offer unique and enticing experiences, but which one should you choose for your city break or holiday?

We recognise the difficulty in making this decision. While there is abundant information available on both destinations, clear guidance on which city better aligns with your travel preferences is often hard to find.
This article aims to provide an impartial comparison,and hopefully help you to choose the best city to visit.

The article is structured into several sections, each of which can be directly accessed through the following links:
• Introduction to the cities
• Scores and ratings
• Which one should I, friends, or family visit?
• When to visit and weather
• Who is the city suited for?
• The perfect 48hours (with map)
• Tourism details (where to stay? airport details?)

Milan, synonymous with fashion and luxury shopping, is a city where appearances matter, and even its main tourist attraction, the Galleria, is a shopping arcade. While the historic centre is home to high-end boutiques and designer stores, the city’s more creative and edgy districts can be found on the outskirts.

Visitors should be aware that Milan that Milan does not have the breadth of monuments and standout tourist attractions as of other Italian cities. This is primarily a business focused city, which reveres in sophistication and looking good.

The beautiful Galleria shopping arcade

Lisbon is a progressive and liberal city, which still retains its rich seafaring history and distinctive Portuguese heritage. The city effortlessly blends history, vibrant culture and exciting nightlife into one charismatic tourist destination.

Lisbon is a city of compact variety; you can get lost in the maze of narrow streets in the Alfama district, be wowed by the grandeur of the plazas in Baixa or join the hipsters and fashionistas in the Principe Real. Close to the city are glorious sandy beaches, and Lisbon boasts one of the finest climates in Europe. This is an amazing city, which you must visit.

The number 28 tram passing the Se cathedral in Lisbon

The gothic Duomo in central Milan – a highlight is the view from the roof

Do you agree with us? Why not provide your own scores for Lisbon here

Summary
Where would I journey for a personal escape?
Lisbon
Where would I send my parents for a memorable visit?
Lisbon
Where's the ideal destination for my adventurous 19-year-old cousin?
Lisbon
Where should my food-obsessed friend indulge their culinary passions?
Lisbon
Note: The above comparisons are weather-independent and are based on travel during the most opportune times of the year. Details about the ideal travel seasons are elaborated upon later in this article.

In the sections that follow, you'll find a comprehensive comparison between these two fascinating cities. This includes recommendations on the duration of stay, the best times to visit, and tailored 48-hour itineraries for each city.
The final segment delves into practicalities for your travels, such as the best airport to fly into, the optimal districts for your accommodation, and insider tips, for when you come to explore the city.

We hope that you find all of this information useful, in planning your next exciting trip!

Lisbon is a diverse and exciting city that you’ll need at least three days to fully see.
Many visitors also include Sintra as part of their stay, but at a minimum, but we recommend spending at least two full days in Lisbon itself.

If you are fortunate enough to have a longer stay, there are many enjoyable day trips, including the palaces of Sintra, the beach resorts of Cascais or the historic towns of Obidos and Evora.

In the summer, you could also visit the beautiful beaches along the Cascais or Costa Caparica coastlines. Best of all, these day trips can all be reached via the inexpensive public transportation.
Related articles: 3 days in Lisbon – 48 hours in Lisbon

The main sights of Milan can be easily seen in a single day of sightseeing. A second day allows time to explore the more atmospheric districts (Navigli, Zona Tortona) or provides extra time for shopping. To capture the essence of the city, you need to experience the early evening drinks culture and the evening strolls where everyone wears their finest clothes.
Milan may lack many tourist sights, but there surrounding region certain compensates with many enjoyable day trips. This includes the historic towns of Bergamo, Brescia and Pavia, the beautiful lakes of Garda, Maggiore and Como, plus the Italian Alps. It is even possible to visit Verona as a day trip.
Related articles: 3 days in Lisbon

A tourist cruise boat passing beneath the Ponte 25 de Abril suspension bridge in Lisbon

The Naviglio Grande canal runs through the heart of the Naviglio district

For the real Milan experience, you want to visit during the summer or winter fashion weeks (Sep/Oct or Feb/Mar), to mingle with models, stylish and Aficionados.

For a city break, Milan is almost year-round, but it is cool and possibly wet in the winter, while in hot August most residents head to the beach for the whole month.

One of the quirks of Milan is at the weekends, most of its affluent or mobile residents leave the city for the coast (summer), the Alps (winter) or lakes (Spring/Autumn), leaving the city to tourists and foreign shoppers.

The recommended time to visit Lisbon is in the late spring and early autumn, when the city is sunny and warm, but without the summertime crowds.

Lisbon is subject to the pressures of over-tourism at times, most notably being incredibly crowded during the summer months in the popular tourist areas, such as the Belem district and Sintra.

Due to the increased popularity of Lisbon, it is becoming a year-round destination, however, be warned that the winter months can be wet and cool.

Our favourite time of year to visit Lisbon is during the first two weeks of June, when the whole city celebrates the Santos Populares festivals with street parties and traditional dances.

Lisbon has a wide appeal; there are cultural sights, a buzzing nightlife and a blossoming artisan scene. The city will appeal to young or old, either for a cultural trip or as a fun weekend away.

In the summer (May-Sep) the beaches make for a really good extension to your trip and are easily accessible from the city. There is little to fault Lisbon and most visitors leave with fond memories of the city.

If you have a passion for fashion, a flair for style, and are willing to indulge in a premium experience, Milan is your destination. The city stands out for its high-end designer shopping, trendsetting fashion, and its overall chic aesthetic.
However, some visitors may find Milan less captivating compared to the grandeur of Rome, the cultural richness of Florence, or the picturesque scenes of Venice. Milan is predominantly a business hub, where the hardworking ethos of its inhabitants is reflected in its cutting-edge fashion and refined nightlife.
Insight: There are few historic buildings in Milan, as many were destroyed by the extensive bombing of the second world war.

The distinctive Castello Sforzesco castle in Milan

There are beautiful beaches only a short train ride away from the centre of Lisbon

There are three airports for Milan; Linate (small dated, 7km to centre), Malpensa (main international airport, 50km from west of Milan) and Bergamo (Ryan air hub, 50km from north east of Milan). There is a bus from Bergamo to Milan (60minutes €6.00), train from Malpensa airport (50minutes €13.00) and from Linate just take a taxi (€12-15). There is no shortage of flights and departures to or from Milan, and fares, if booked far enough in advance, can be very cheap.

Milan has ample hotels and accommodation options, but these obviously need to be booked far in advance during the two fashion weeks. For your first visit you would want to be based close to the historic centre (Centro Storico) or for a more lively and authentic experience the Navigli district. For cheaper accommodation look to the Citta Studi, the main student area of the city. Milan has very good public transport, and is easy to travel around the city.

The Arco della Pace, in Milan