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WhereToGoForMyHoliday.com

The best destination comparison site!

Tallinn or Milan, which is better for your holiday in 2024?

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?)

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.

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.

Duomo milan

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

Tallinn Estonia

Medieval towers dominate the skyline of central Tallin

Milan vs Tallinn: City Ratings

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!

Destination details

How long to spend each 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.

Naviglio Grande milan

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

Suur Rannavärav Tallinn

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.

Castello Sforzesco castle  Milan

The distinctive Castello Sforzesco castle in Milan

Toompea Castle Tallinn

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

48 hours in Milan
The interactive map below shows a suggested tour for 48hours in Milan. The first day is shown in green and the second day is marked in yellow.

Day 1: Start your first day at Piazza del Duomo, the vibrant heart of Milan. This square is home to the stunning Gothic Duomo di Milano cathedral (be sure to visit the roof for spectacular views) and the elegant Galleria shopping complex, which houses a range of boutiques and high-end retailers. On the other side, you'll find the Palazzo Marino and the prestigious Teatro alla Scala.

In the afternoon, take time to explore the area around the Sforza Castle and Parco Sempione. Make sure to visit the Santa Maria delle Grazie convent, where you can admire the renowned “The Last Supper” fresco. Later, explore the fashionable Brera district, known for its blend of luxury stores and stylish residents.
Early evening is when Milan truly comes alive. As the workday ends, locals flock to bars for Apericena (a happy hour accompanied by a light buffet), where they enjoy fine cocktails and showcase the latest fashion trends. The Navigli district is an excellent spot to immerse yourself in this contemporary cultural tradition.

Santa Maria delle Grazie milan

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

Day 2: For your second day, take a stroll from the Duomo, along the lively Via Torino, and continue onto Corso di Porta Ticinese, passing the impressive Basilica San Lorenzo Maggiore before entering the vibrant Navigli district. This canal-lined quarter brims with artisanal shops, trendy bars, and is a popular haunt for the city's youthful population.

The canals and train lines mark the boundary between Navigli and Zona Tortona, a district that has transformed from its gritty past to become Milan's hub of design and creativity. Today, designers breathe new life into former warehouses, creating the latest fashion trends. The area is subtly cool and epitomises the determination and fervour of Milan's residents.
For football enthusiasts, a tour of the iconic San Siro stadium is a must on your second day in the city.
Related articles: 48 hours in Milan

San Siro stadium milan

San Siro stadium, home to two of Italy’ greatest football teams

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 view point

The view over the historic centre of Tallin

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.

For hotels, the ideal location is the Lower Town. Generally speaking, the closer you get to Town Hall Square, the pricier the establishments become. But you might not even want to be there – it's buzzy and loud. The streets further north and east are laced with other B&Bs and even hostels and are still within walking distance of the monuments. The areas of Tonismagi and Tatari are good alternatives if you're really looking to keep costs low.

The ferry terminal in Tallinn

The ferry terminal in Tallinn

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.

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.

Arco della Pace Milan

The Arco della Pace, in Milan

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