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Milan or Lisbon; a city comparison and tourism travel guide

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

Lisbon is a city of compact variety; there is a maze of narrow streets in Alfama, the grandeur of Baixa’s plazas or the refinement of Principal Real. The region has one of the best climates of Europe and there are even glorious beaches close by. Lisbon is an amazing city, but having been fully discovered by mass tourism, it is starting to display the early signs of over-tourism…

About this guide: We understand that selecting a destination is challenging and sometimes overwhelming, especially when every web guide or travel book makes each city seems so incredible and memorable.

Choosing a destination is not just about the famed sights of the city, it is also the ambience of the city, the suitability of the weather and if it aligns with your passions and interests.

High-level summary

Summary
Which city would I go to? Lisbon
Which one would I recommend to my parents? Lisbon
Which location for my 19-year-old cousin? Lisbon
Which for my food obsessed friend? Lisbon
Note: The above comparison does not consider the weather, and assumes travel at the best time of year (which is detailed later in this article)

The following sections compare the two cities and considers; how long to spend in them, when to visit, and provides suggested 48hours in each city (along with an interactive map). The final section is tourism practicalities and includes which airport to fly into, what district to be based in and how best to explore the city. We hope that you find all of this information useful, in planning your next exciting trip.

Destination details

How long to spend in the city?

Lisbon is a varied city with many fascinating districts and tourist attractions. The city takes three days to fully explore, but could be condensed into two days to provide a day trip to beautiful Sintra.
Equally a trip could be extended to five days, by including Sintra, the pretty coastal town of Cascais and a visit to the glorious beaches (May- September). Within the Lisbon region, there are sufficient day trips, beaches and activities to easily fill a one-week holiday.

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

When to visit?

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 season to visit Lisbon is in the Spring and Autumn. Lisbon is now very popular in the summer months, especially the day trips to Sintra and Belem district. Lisbon is starting to become a year-round destination, but be warned that the winter months can be overcast and wet. Our favourite time of year to visit Lisbon is the first two weeks of June, when there are street festivities called the Santos Populares.

Is it for me?

Lisbon has a wide appeal; there are numerous cultural sights, great 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 can be visited and there are many enjoyable day trips to an extended trip. There is little to fault Lisbon and most visitors leave with fond memories of the city.

If you adore fashion, embrace style, and willing to spend a little extra, then Milan is calling you. The city excels in designer shopping, trend-setting, and simply looking good.

Many visitors leave Milan slightly disappointed; it is without the flare of Rome, the culture of Florence, or the photo opportunities of Venice. Milan is a business city, where the reward for the industrious attitude of its residents, is cutting edge fashion and sophisticated nightlife.
Insight: There are few historic buildings in Milan, as many were destroyed by the extensive bombing of the second world war.

The perfect 48hours

There’s a lot to squeeze in for 48 hours in Lisbon.
Below is an interactive map of this tour - day 1 is highlighted in green and day 2 in yellow, with optional sights and section in grey.

Most tours begin in the Baixa district with its grand avenues and magnificent plazas, such as the Praça do Comércio. In the later part of the day start to climb hills into the Alfama district, which is a maze of narrow streets leading to the castle. Take in one of the viewpoints close to the castle for a romantic sunset and then ride the quaint number 28 tram as it rattles through the city.

For dinner head into the Baixa district and then for nightlife its Barrio Alto, with its funky bars and socialising which fills the streets.

Torre de Belem lisbon

The Torre de Belem once guarded the Tejo Estuary and Lisbon

For the second day head to the Belem district, which contains the Mosteiro dos Jerónimos, and Torre de Belem, along with views across the Tejo Estuary. For the second part of the day discover the stylish Príncipe Real and Avenida da Liberdade districts or visit the ultra-modern side of Lisbon, the Parque das Nações.

48 hours in Milan.

Begin the first day at the Piazza del Duomo, the heart of Milan. On this plaza is the gothic Duomo di Milano cathedral (head to the roof for amazing views) and the beautiful Galleria shopping complex, filled with boutiques and exclusive retailers. On the opposite side is the Palazzo Marino, and the elegant Teatro alla Scala.

For afternoon explore the sights around the Sforzinda castle and Parco Sempione. Do include the Santa Maria delle Grazie convent, where the famed “The Last Supper” fresco is housed. For the latter part of the explore the chic Brera district, with its mix of high-end stores and fashionable people.
The early evening is when Milan excels, as the offices close and workers head to the bars for Apericena (happy hour with light buffet food) to drink exquisite cocktails and flaunt the latest fashions; Navigli is a great area to experience this modern cultural tradition.

Santa Maria delle Grazie milan

The Santa Maria delle Grazie convent, the location of one of the most controversial religious paints….

For the second day, wander down from the Duomo along the bustling Via Torino and then the Corso di Porta Ticinese, passing the Basilica San Lorenzo Maggiore, and enter the atmospheric Navigli district. This canal district is filled with artisan shops, fashionable bars, and where young Milanese frequent.

The canal and train lines separate Navigli from Zona Tortona, the once-gritty but now design and creative hub of Milan. Here designers create the latest fashions in the former warehouses. Understatedly cool, but the place to experience the drive and passion of the Milanese.
If you are a football fan, you probably want to include the tour of the San Siro stadium, in the second day.

Tourism Practicalities
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