Spending Weekend in Tallinn – 3 Days Unique Itinerary With Local Insight

This 3-day in Tallinn itinerary is based on how I actually recommend people spend a weekend in Tallinn — not just ticking off tourist sights, but seeing the city from a more personal, less standard perspective, kind of the way locals do.

It’s not “local” in the strict sense, because there’s not one particular way locals experience Tallinn, but this is the version I’ve come to know after living here for a year. I’ve packed this route with variety — different neighborhoods, moods, viewpoints, and small details that will make your visit interesting. So you get a chance to explore Old Town and also what is there outside Tallinn city center.

A weekend is a short time, but it’s enough to get acquainted with the old town and surroundings, and I’m confident this itinerary will help you do just that.

By the way, it is designed for good weather (late spring through early autumn in the city), but works well in winter too if you make a few swaps to indoor activities. So if you plan to be in Tallinn in December while visiting Christmas markets, my route will come in handy too!

How to Spend 3 Days or a Long Weekend in Tallinn

Day 1 in Tallinn: Arrival, Settle in Kalamaja & Explore Old Town on Foot

If you’re spending a weekend in Tallinn and arriving on Friday, base yourself in Kalamaja, a former fishing district just northwest of the Old Town.

This neighborhood dates back to the 14th century and became home to fishermen, dock workers, and factory laborers during the industrial era. While much of the area has been revitalized, it’s still full of wooden houses built between the late 1800s and early 1900s — many of which are now protected under heritage status.

Today, Kalamaja is a quiet, residential neighborhood with cafes, independent shops, and a slower pace than the city center.

To me, it’s a fantastic place to stay if you like waking up in unique neighborhoods with history and want walking distance to major sights, but prefer to avoid tourist-heavy areas. From here, it’s about 10-15 minutes on foot (depending on the exact location) to the gates of the Old Town.

Drop Bags & Start the Walk

Once you check in, skip buses or taxis and head out on foot. Begin your walk along Vana-Kalamaja Street, one of the main historic streets in the district (you can see it in my photo below). It recently underwent a renovation to become more pedestrian-friendly and bikeable, with wide sidewalks and calm traffic. You’ll pass restored wooden houses and a few casual cafes.

Make a quick stop at Balti Jaama Turg, the central market. In summer it is open until 7 PM and worth popping into if you’re early enough.

Downstairs you’ll find fresh produce, baked goods, and Estonian specialties. The second floor features a mix of vintage clothing, Soviet-era memorabilia, and modern Estonian design — good for browsing even if you’re not shopping.

Head to the Viewpoints — Start with Patkuli

After the market, walk toward Nunne Street, then turn onto the stone staircase (will be on the right when walking from Balti Jaama) that leads to the Patkuli viewing platform.

This platform is built right into the city wall and gives you a direct view over Tallinn’s red-roofed skyline, the medieval wall, and the railway station below. It’s my favorite because of its open angle and clear layout of the city’s different angles — from Old Town spires to Kalamaja’s rooftops and sea in the distance.

The stone staircase you just climbed is also one of the oldest access points between lower and upper Tallinn, connecting what were once distinct social and political zones in the medieval city.

Continue to Kohtuotsa Platform

From Patkuli, walk east through Toompea and make your way to the Kohtuotsa viewing platform. This one is more spacious, often busier (because everyone likes to come here), and gives you a wider perspective, especially of Tallinn’s business district, church towers, and the harbor.

The now-iconic “Times We Had” graffiti is painted on the wall here, and this is where you’ll see locals taking graduation or engagement photos in summer. The view is less focused than Patkuli, but it’s broader — good for understanding how compact the city is.

Pass by Alexander Nevsky Cathedral

From there, continue to Alexander Nevsky Cathedral, a Russian Orthodox church built in 1900 when Estonia was part of the Russian Empire. The church was intentionally placed on top of Toompea Hill, facing the Estonian parliament building as a political and religious statement.

Its five onion domes, black roof, and over 10 bells (including the largest church bell in Tallinn) make it architecturally unique in the city. You can enter for free, where you’ll hear church music playing throughout the day.

Bishop’s Garden & St. Mary’s Cathedral

Walk behind the cathedral to reach Bishop’s Garden — a small, tiered garden area on the edge of the wall. It’s not manicured, but it’s peaceful, with benches, old trees, and a view toward Kalamaja. The area is named after the bishops who lived nearby in the medieval era, though the modern garden layout is more recent.

A few steps away is St. Mary’s Cathedral (Toomkirik) — Tallinn’s oldest church, originally built as a wooden structure in 1219 and later rebuilt in stone in the 14th century.

It usually closes at 4 PM, so on the first day in Tallinn in the evening, you won’t be able to go inside, but you can return on the following day, since it’s quite interesting to see a large collection of coats of arms from noble families buried here. This church served as the burial site for the Baltic-German aristocracy.

End the Day at Danish King’s Garden (Taani Kuninga Aed)

Before heading down to the lower town, walk over to Danish King’s Garden. This quiet courtyard is where legend says the Danes received their red-and-white flag (the Dannebrog) during a battle in 1219. Three life-size monk statues stand silently around the edges — a bit eerie, especially in the evening.

There’s a small lookout point over the rooftops, and a narrow stone passage that leads down toward the lower town if you want to skip the main staircase.

Into Old Town for Dinner

Descend into the Old Town via the nearby Lühike jalg street or take the stairs down Pikk jalg — both are scenic stone streets with old buildings and lanterns.

Eventually, you’ll reach Raekoja plats — Tallinn’s main square, where the Town Hall (Tallinna Raekoda), built in the early 1400s, still stands. It’s the oldest surviving town hall in Northern Europe and served as both an administrative and social center.

This is where I suggest you stop for dinner because you’ll find a few interesting restaurants there with an old town feel. A few places I like:

• Restaurant Pegasus – just off the square. Well-known among locals, with modern Estonian dishes using seasonal ingredients.
• Mix Restaurant – closer to the Old Town walls, this one is a mix of European and Asian touches. Good if you want something creative but not too experimental.
• If you want something traditional and tourist-friendly, choose one of the medieval-themed places on the square, but check reviews — quality varies.

After dinner, take a slow walk back to Kalamaja or jump on a bus #3 or #73, depending on where exactly you stay in the neighborhood. You’ll likely find the Old Town emptier by evening hours, with lantern-lit streets and quiet corners.

If not too tired and like going to bars, after returning back to Kalamaja, go for drinks to Põhjala Tap Room. It’s just one awesome brewery where to have beer (they brew 22 types of beer here) together with in-house-made appetizers. Although you can also have dinner here too since they prepare very good meals, including Texas BBQ.

Day 2 in Tallinn: Seaside Walks, Pirita Beach & a Local Evening Out

If you’re spending a full weekend in Tallinn and following this local itinerary, your second day is a chance to see what most tourists skip — areas beyond the medieval walls that still carry Tallinn’s character, just in a different rhythm. Instead of going straight back to Old Town, start your morning a little differently.

Morning: From Kalamaja to Noblessner Waterfront

Since you’re staying in Kalamaja, take some time to explore it more deeply. This part of Tallinn used to be a working-class area for fishermen and factory workers, and today it’s one of the most walkable and relaxed neighborhoods in the city. Wooden houses, small cafes, playgrounds, and everyday life — it’s a big contrast to the Old Town’s tourism flow.

From there, walk toward Noblessner, a former submarine factory complex that has been fully transformed into a modern seaside district with contemporary architecture, harbor views, high-end apartments, cafes, and design shops — all wrapped in post-industrial style. It feels polished and spacious, with open skies and sea breeze.

Continue your walk along the new pedestrian path that connects Noblessner with Kalarand (also called Kalaranna rand). This seaside promenade only opened recently and has made it much easier to walk along the water without interruption.

The route takes you past the Seaplane Harbour Museum (Lennusadam) — an impressive attraction in its own right, one you could easily spend a full day exploring. But on this short itinerary, especially if it’s your first time in Tallinn, there isn’t enough time to go inside. Still, walking by gives you a glimpse of the massive hangars and historic naval vessels docked along the pier, a fascinating sight even from the outside.

Breakfast Break Nearby

After your quick seaside walk, stop for a late breakfast with coffee in one of the cafes nearby. Many of my favorite spots are around Kalamaja and Noblessner — I’ve listed them in this Tallinn breakfast and brunch guide, so you can pick depending on your mood (pastry, full brunch, or coffee with a view).

Midday: Walk Through Rotermann & Modern Tallinn

Next, make your way through Rotermanni kvartal, just 15–20 minutes on foot from Noblessner or a short tram ride. This is Tallinn’s renovated warehouse district, now filled with boutiques, restaurants, and modern apartment buildings. What makes it interesting is the mix of old and new — 19th-century grain storage buildings now house sleek restaurants and glass-walled offices.

From here, go grab one of the most delicious cinnamon rolls and continue walking past Viru Keskus (Viru Mall). No need to shop — just notice how life feels outside the historic core. You’ll pass green parks, office blocks, and tram stops filled with locals, giving you a sense of Tallinn’s modern daily rhythm.

From this area, it’s just a short tram or bus ride to Kadriorg, a quiet, elegant district built around a large park and palace commissioned by Peter the Great — worth a quick stop before continuing to Pirita.

Afternoon: Half-Day Escape to Pirita

If the weather’s pleasant — and between May and October it often is — take advantage of the sunshine and head to Pirita, one of the best spots to escape into nature without leaving the city.

To get there, hop on bus 1A or 8 from the Viru area. It’s a quick 15–20 minute ride and drops you near the beach.

Once there, take a walk along the beach promenade — Tallinn’s main stretch of sand with open sea views and the city skyline in the distance. Nearby, you’ll find the ruins of Pirita Convent, a 15th-century monastery destroyed during war but still standing as a striking stone shell.

Also, walk through the marina or along one of the forest trails just beyond, where Tallinn’s largest green zone begins.

Expect to spend about 2–3 hours in Pirita (or even more), especially if the weather holds and you want to spend some time on the Baltic Sea.

By the way, below in my short is Pirita’s forest area in winter. If you happen to come to spend a weekend in Tallinn from late fall to spring, you can definitely visit this area too. It’s interesting to see the frozen sea at that time.

Late Afternoon/Early Evening: Return to the Old Town (Optional)

Come back to the Old Town in the late afternoon to walk more and check out other streets that you didn’t get to see on Day 1 — explore hidden courtyards, get a traditional meal at Peppersack or Olde Hansa.

This is also a good time to join an evening Old Town Ghost Tour or just walk the smaller streets and take photos without the usual foot traffic.

Evening: End in Telliskivi for Food & Nightlife

Wrap up your second day in Tallinn in Telliskivi Creative City, right next to Kalamaja. This former industrial zone is now Tallinn’s number one area for bars, breweries, and casual restaurants.

It’s also home to Fotografiska, a world-class photography museum with a rooftop restaurant and terrace. It closes at 8 PM on Saturday, which is convenient if you like art and want to fit in an art museum visit in the evening.

Day 3: Morning in Nature – Viru Bog Hike

To finish your weekend in Tallinn, I recommend leaving the city for a few hours to experience something truly unique to Estonia: the bog landscapes. Locals often go for bog walks on weekends, and if you’ve never seen one, this is your chance.

The best and most accessible option is the Viru Bog (Viru raba), located in Lahemaa National Park, just under an hour from Tallinn. What makes this bog special is its well-maintained 3.5 km wooden boardwalk, which takes you through pine forest, open peatland, and wetlands with a watchtower where you can get a panoramic view of the mossy, lake-speckled landscape.

It’s peaceful, atmospheric, and feels nothing like the city, especially in the early hours, when the light is soft and the trail is quiet.

To get there, the easiest option is to join a guided tour. Tours typically start in the morning and last around 5–6 hours total, including transport. I link one here that I recommend. You’ll have time to grab breakfast in Tallinn before heading out, and be back by mid-afternoon.

Alternatively, you can go by public bus, but buses to the Viru Bog stop are infrequent. If you miss one, you may end up wasting time waiting, so this option only works if you have more time in Tallinn and aren’t catching a flight that day.

Another option is to rent a car, which gives you full flexibility. This is how we visited Viru Bog, and it was a smooth, easy drive. You can pick up a car directly at Tallinn Airport, which is on the way to the bog – compare prices here.

Don’t leave Tallinn without seeing a bog. It’s a part of Estonia’s natural identity, and a totally different kind of beauty that most travelers miss if they stay only inside the Old Town.

More Ideas for How to Spend 3 Days in Tallinn

If you’re spending 3 days in Tallinn and want to customize your itinerary, there are a few great alternatives such as:

One powerful stop is the Vabamu Museum of Occupations and Freedom, which offers a deep and emotional look into Estonia’s 20th-century history under Soviet and Nazi rule. Another incredibly interesting place is the Carved Stone Museum (Raeapteek’s stone cellars), which takes you underground into old limestone storage rooms beneath Tallinn.

I also like the Estonian Open Air Museum and Nõmme neighborhood, but you’ll need to leave them for another trip to Tallinn, because one weekend is not enough to cover everything.

Planning to travel in the region?

If you are exploring more of the Arctic and Nordic countries, here are a few guides you might like:

• How Much Does a Trip to Tromsø Cost – detailed breakdown of prices
• Lapland on a Budget – how to visit it without overspending
• 7 Days Lapland Itinerary – detailed route for a winter trip
• Norway on a Budget – my personal tips and experience

More Weekend Getaways in Europe

Here are more itineraries from my travels — all based on routes I personally created and explored:

• Weekend in Vilnius – my favorite way to spend a getaway there
• Weekend in Prague – 2 days very fast-paced itinerary
• Long Weekend in Budapest – step by step itinerary for 3 days
• Weekend in Malaga – best route for first timers
• One Day in Istanbul – 2 different itineraries depending on the airport where you land
• Day in Podgorica – the best way to explore Montenegro’s capital
• Europe Weekend Getaways – my other itineraries, designed for personalized travel around Europe