Tallinn is the kind of city that rewards slowing down. Most people arrive off a Baltic cruise, march the cobbles of the Old Town for two hours, snap the red rooftops from a viewing deck, and leave thinking they have seen it. They have seen the postcard. They have not met the city.
Anna-Elina has spent years closing that gap. She is a Tallinn-born local guide who leads small-group walking tours through the medieval Old Town, the parks and palace of Kadriorg, and the seaside districts that most day-trippers never reach. She started out guiding in Italian, joined Lokafy two years ago after spotting a post about our growing community of local hosts, and she has been showing visitors her hometown ever since. She speaks Italian, Russian, and English, all fluently, which comes in handy the moment a menu turns out to be written only in Estonian.
We sat down with Anna to talk about the corners of Tallinn she loves handing to travelers. Here is where she takes them, and how you can see the city the way she does.
Meet Anna-Elina, your local in Tallinn
Anna guides because she likes people and she likes her city, in roughly that order. Ask her what keeps her going and the answer is not complicated.
"My favourite part of being a Lokafyer is telling tourists about the history of Estonia and Tallinn, and creating a fun and positive atmosphere during trips."
She was born here, so Tallinn is not a job she commutes to. It is home. She grew up with the song and dance festivals, the flower gardens, the black-white-and-blue flag, and the medieval Old Town that UNESCO added to its World Heritage list. That closeness shows up in the small stuff: which alley leads somewhere worth the detour, which cafe still does coffee and cake the old way, which courtyard behind a merchant house you would walk straight past on your own.
Tallinn Old Town: medieval streets and the view from Toompea
Tallinn's Old Town is one of the best-preserved medieval city centres in Europe, and Anna treats it as more than a photo backdrop. The walls are largely intact. The guild houses, the merchant homes, the spires of St. Olaf's and Town Hall Square all sit close enough to cover on foot in an afternoon.
The part first-timers miss is the climb up to Toompea, the Upper Town, where the viewing platforms look out over the whole tiled sprawl toward the harbour. Anna walks guests to each of them.
"We looked out over our city from all five viewing platforms of the Upper Town and took photos to commemorate the trip."
Kohtuotsa is the famous one, the terrace with the ships and the red roofs and usually a busker or two. Patkuli, on the other side, gives you the train station, the sea, and a slice of the old town wall with its towers lined up like chess pieces. Doing all of them in one loop is the sort of thing you would not think to do without someone who knows the order to walk them.
Tips for the Old Town
- Wear real shoes. The cobbles are uneven and slick after rain.
- Start early or go late afternoon to dodge the midday cruise crowds.
- Look up. The best carvings and dates are above eye level, on the guild houses.
- Ask your guide what the buildings actually were. Half of them have a story that is not on any plaque.
Kadriorg: the park, the palace, and the swan pond
When Anna wants to show travelers a different side of Tallinn, she takes the tram out to Kadriorg. It is a short ride from the city centre, ten or fifteen minutes, and it drops you into a green world of paths, fountains, statues, and ponds that feels a long way from the cobbles.
At its heart is Kadriorg Palace, the baroque summer palace Peter the Great built for Catherine, with formal flower gardens out front. The grounds are also home to KUMU, Estonia's main art museum, if you want to duck indoors. Anna's own memory of the place is a simple one, and it is the reason she keeps bringing people back.
"We admired the palaces and wooden villas, and also drank coffee and cake on the summer terrace by the historic swan pond."
That is the tour in miniature: a little history, a little walking, and a pause for cake by the water before you head back to town. From Kadriorg you can carry on toward the seashore and watch the Tallinn skyline stack up behind you, towers in front, the enormous ferries sliding in and out of the harbour.
Kalamaja: the old fishing village by the sea
Kalamaja is where Anna sends travelers who want the lived-in Tallinn, the one locals actually spend their weekends in. It is an old fishing village on the coast, a short walk from the Old Town, full of wooden houses painted in faded colours and a fish market that still does its job.
The name means "fish house," which tells you most of what you need to know about its past. These days it is cafes and small shops sitting next to that history rather than replacing it. Anna likes it because it is honest. You get the sea, the timber architecture, and a neighbourhood that never bothered to dress up for tourists.
Why go to Kalamaja
- It is close, so you can fold it into an Old Town day without much effort.
- The wooden houses photograph beautifully in soft light.
- The fish market and small cafes are a good, unfussy lunch stop.
- It pairs well with a walk along the water toward the port.
The Song Festival Grounds and Tallinn's living traditions
If you have five minutes to understand Estonia, Anna will spend them on the song festival. Every five years the country gathers at the Song Festival Grounds, thousands of singers on one enormous stage, for a tradition that helped carry Estonian identity through a century of occupation.
"There's the local song and dance festival, organized and held every five years. I prefer the Song Festival area. We go there, learn about its history, and see many images that tell history."
Even when there is no festival on, the grounds are worth the visit, and concerts and food events fill the space through the year. Standing in that empty arch, hearing what it means to the people who sing there, does more for your sense of Tallinn than another lap of the Old Town would.
Anna's hidden gems: bastion parks and merchant courtyards
Ask Anna for the spots that do not make the guidebooks and she goes to two places.
The first is the bastions. Tallinn turned its old defensive earthworks into green hills dotted with sculptures, gardens, and quiet views back over the rooftops. Locals treat them as parks. Most visitors never climb them.
"During our tours we can climb the bastions where the city has created parks, admire the sculptures and gardens and views that tell us history. I also enjoy showing travelers the courtyards of merchant houses."
The second is those merchant courtyards, tucked behind Old Town facades, where you can see how the trading families actually lived. You would walk past the doorways every time without a local to steer you through them.
A quick word on the food
Estonian cooking is plain in the best sense, hearty and seasonal without much fuss. Think dark rye bread, marinated herring, forest mushrooms, and the marzipan Tallinn has been making since its apothecary days. Anna's approach is to tell you what Estonians actually eat and let you pick.
"As local Estonian cuisine is simple and tasty, I always tell guests about what Estonians produce and eat, and they decide for themselves."
Why seeing Tallinn with a local matters
You can find the Old Town on a map. What a map will not do is tell you which viewing platform to hit first, why the song grounds make grown Estonians cry, or how to order the good thing off a menu printed in a language with fourteen cases. A local guide like Anna handles the translation and the context both, so a wall stops being a wall and starts being the reason the city survived.
Her advice to travelers sums up her whole approach.
"Talk to your local guide, listen to stories about the area's history, folklore, and tips, then put those tips into practice right away and take photos to preserve the memories of your trip."
Explore Tallinn with a local
Ready to see Tallinn through Anna's eyes? Walk the medieval Old Town, climb to the viewing platforms of Toompea, take the tram to Kadriorg for coffee by the swan pond, and wander the wooden lanes of Kalamaja by the sea. A local guide can translate, tell you the stories behind the stones, and shape the day around what you actually want to see.
Explore Tallinn like a local with Anna →
Frequently asked questions about visiting Tallinn
What are the best things to do in Tallinn? The medieval Old Town and its Toompea viewing platforms, Kadriorg Park and Palace, the Kalamaja fishing village by the sea, and the Song Festival Grounds are the highlights. A local walking tour ties them together in a single day.
How long do you need in Tallinn? One full day covers the Old Town and one nearby district like Kadriorg or Kalamaja. Two days lets you add the seaside walk and the Song Festival Grounds without rushing.
Is Tallinn Old Town worth visiting? Yes. It is one of the best-preserved medieval city centres in Europe and a UNESCO World Heritage Site, with intact walls, guild houses, and open viewpoints over the red rooftops.
Can you do a Tallinn tour in English? Yes. Lokafyer Anna-Elina guides in English, Italian, and Russian, so a language barrier is not a problem on tour or when ordering off an Estonian menu.
What is the best way to explore Tallinn like a local? Book a small-group walking tour with a local guide. You get the history, the hidden courtyards and bastion parks, and food recommendations you would not find on your own.
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