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Tallinn or Milan; a vs city comparison and travel guide

Both Tallinn and Milan are fantastic cities, but which is better 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 divided into the following sections, and can be jumped to using the underlined links:
1) Introductions -
2) City ratings -
3) Which one should I, friends, or family visit? -
4) When to visit and weather -
5) Who is the city suited for? -
6) The perfect 48hours (with map) -
7) Tourism details (where to stay? airport details?)

Introduction to Milan and Tallinn

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.

Mention the name Milan, and it instantly conjures up visions of fashion, refinement and exclusive shopping. This is a city where looking your finest is an obsession, and even the main tourist attraction, the Galleria, is shopping arcade. Luxury brands and designer boutiques may fill the historic centre but out on the outskirts are edgy districts where this creativity originated from.

As a visitor, you should realise 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.

Milan vs Tallinn: City Ratings

Summary
Which city would I go to?
Tallinn
Which one would I recommend to my parents?
Tallinn
Which location for my 19-year-old cousin?
Tallinn
Which for my food obsessed friend?
Tallinn
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?

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.

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 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.

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.

48hours in Tallinn
Wander the Lower Town, see Russian-style cathedrals, taste medieval broths in immersive eateries, gaze at the frothing Baltic waves, duck under ancient fortification walls – all that and more should be a part of any two-day itinerary for the Estonian capital…

Day 1: The Town Hall Square (Raekoja plats) at the very core of the city is always the perfect place to begin. Go there and the sightseeing will start immediately. The eponymous Town Hall itself is the main attraction. It's a beautiful 36-meter structure with a tower that's topped with the Old Thomas weathervane, now a symbol of the city. You're also at the perfect starting point to get lost in the Lower Town of Tallinn.

That's the largest part of the historic center, a UNESCO site, and the place where merchants and guilds would once have plied their trade. Viru Street is one not to miss within. It's a hubbub of shops and eateries, all leading to the handsome Viru Gate, which dates all the way back to the 14th century. A whisker to the north is the Hellemann Tower, offering travellers access to a high lookout point and a 200-metre stretch of the City Walls.

Once you're back on dry ground, delve into the Lower Town once again, going north via Pikk Street. At its end you'll emerge into the hipster area of Kalamaja. Boho coffee shops and Mexican eateries combine there, but the best way to spend the evening is in the block behind Tallinn's train station, where industrial-chic cocktail bars like St. Vitus mix up creative long drinks.

Raekoja plats Tallinn

The Raekoja plats plaza is at the heart of Tallinn

Day 2: The early hours see you head above the Lower Town to Toompea Hill. Once the main keep and most fortified part of the historic city, it's still one of the most important postcodes in Estonia. On one side is the soaring Alexander Nevsky Cathedral, sporting onion domes and filigrees that evoke the Russian Empire.

On the other is St Mary's Cathedral, the oldest in the city. This is also the home of the modern Parliament of Estonia. On sunny days, the views across the historic town from Kohtuotsa are some of the best going, taking in the Paks Margareeta tower in the distance and Town Hall Square below.
Descend from Toompea and go back to the centre to find the immersive tavern of III Draakon. A fun-filled character pub, it's got food that mimics the diet of the 1400s and curt service to match. As evening draws in, pinpoint the nightlife hubs of Rataskaevu and Voorimehe for something a little hedonistic!

Tallinn Airport is small, but it's served by low-cost carriers coming in from Scandinavia, Russia, and Western Europe. It's only a few miles from the Old Town, and the trip can be done on bus number 2 or with a private taxi – expect to pay in the region of €7-11 for that. Other travellers might come across the Baltic on ferries from Helsinki. They cost about €20 and go several times throughout the day from the port in Finland.

Tallinn is a very safe place to travel. It's got low crime rates, and, aside from the ubiquitous pickpockets and taxi scammers, there's rarely any serious issues. Some people have reported extortion scams in nightclubs, but that tends to be limited to the more unsavoury establishments that we think it's best to avoid anyway.

Tallinn is pretty compact and small for a European capital. It's long since burst the seams of its old core, but most of the main sights, bars, pubs, cafés, and museums are still hemmed in by the medieval walls. That means you'll usually be able to walk pretty much anywhere you want. Just be wary of cyclists in the narrow Lower Town streets and icy cobbles in the winter months. Both can be dangers.

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