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

We understand your dilemma. There is an abundance of travel guides for both cities, but few actually comparing them, and advising you which is the better for your trip.
This article will provide our unbiased and independent views of Milan and Tallinn, hopefully making your choice that little easier.

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?)

You could be forgiven for thinking you'd been plucked from the 21st century and dropped back in the 1300s when you step foot in Old Town Tallinn. Cobblestone lanes braid their way through stooped taverns with drooping roofs, chimney stacks, and grey stone keeps that echo The Lord of the Rings.

Aged Toompea Hill is the anchor of it all, erupting above the capital with its muscular castles and onion-domed churches. Below, the Lower Town buzzes with energy, pitting beer bars next to Baltic eateries and church steeples.

Tallinn has also established itself as one of Europe's most cutting-edge cities in recent years. It's a digital powerhouse with start-ups and creative agencies galore. They fuel areas like Kalamaja, which is all roaster coffee joints in Soviet tenements and funky bars in rundown prisons that spill into the Baltic Sea, proving it's not all about the history in these parts…

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

Medieval towers dominate the skyline of central Tallin

Summary
Where would I journey for a personal escape?
Tallinn
Where would I send my parents for a memorable visit?
Tallinn
Where's the ideal destination for my adventurous 19-year-old cousin?
Tallinn
Where should my food-obsessed friend indulge their culinary passions?
Tallinn
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!

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.

Tallinn might not be the biggest European capital, but it's a place that always seems to have another secret up its sleeve. Yes, two days might be enough to see the old city walls, wander Toompea Hill and sample the delights of the Estonian kitchen, but there's certainly enough to fill trips of four, five or even more nights.

Have a think about what you're after from your travels and then decide. If you're eager to squeeze in a few nights on the town (a good shout, as Tallinn is downright hedonistic), daytrips to the wonderful forests and coast swamps of Lahemaa, and a couple of the museums, you'll probably want to give yourself some extra time.

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

The Suur Rannavärav (Great Coastal Gate) protected Tallinn from seaward invasion

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 summer is considered to be the finest time in the Tallinn. From around May onwards, the temperature picks up to the high teens and early 20s, there's more sun, and the days are longer. From June onwards, the travellers and the crowds come, lending a buzz to the bars of the Lower Town.

There's no question that Tallinn looks downright gorgeous under plumes of snow in the midwinter. Some say it's the most enchanting time of all, as the nights draw in and there's ice glinting like diamonds on the roofs of the old churches. On the main Town Hall Square, you'll also be able to enjoy the delights of the Tallinn Christmas Market from early December onwards – think handmade Estonian decorations, hot wine, and traditional pastries. Don't expect to be warm, though. The Baltic gets sub-zero and bitter winds all throughout the season.

If you're keen to go a little off the beaten path and discover somewhere laced with rich history and culture, Tallinn is beckoning. With more and more low-cost flights now serving the local airport, a trip to this north-eastern corner of the continent isn't the chore it once was.
So, anyone eager to ditch the mainstay cities of Western Europe is in luck. Adding to that is an Old Town that's been called the best-preserved medieval quarter in the world, so there's loads for fans of original architecture and atmospheric neighborhoods.

Being so far north means there's nothing like the warmth of the Med or southern Europe up in these reaches of the Baltic. Yes, the summer months can get hot and the sea is only a stone's throw from the city, but Tallinn is hardly a beach destination.
Also remember that this is a small capital by global standards. It's certainly not the pick for anyone on the hunt for a colossal, electrifying metropolis.

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

The Baroque wing of the Toompea Castle, is also the parliament building for Estonia

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