A Day Trip From Helsinki To Charming Tallinn, Estonia

Tallinn’s red roofs and green spires captured my imagination several years ago, and a visit had been on my travel short list ever since (including my inaugural “places I’m dying to visit” list).

So the second I booked my flight to Helsinki, I made sure that my itinerary would include some time in Estonia’s charming capital.

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Why should you visit Tallinn?

Tallinn is a charming and cozy capital city with an almost fairytale atmosphere.  Different eras of historical and cultural legacies are layered on top of each other in a vibrant urban environment.

The medieval Old Town is the city’s heartbeat, and a UNESCO World Heritage site.  It offers beautiful old pastel buildings, cobblestone streets, ancient city walls, soaring church spires, and one of the best-preserved historic centers in Europe.

Tallinn itself is a modern, high-tech city that’s clean, safe, affordable, and has a fun, relaxed vibe.  Its coastal climate gives the city generally milder weather than those around it (making winter a surprisingly good time to visit).

I had originally managed to squeeze in not only a Tallinn day trip in my itinerary, but an overnight as well.  Unfortunately as some intra-Finland flight details were firmed up and ferry schedules changed, we had to lose that night in Tallinn.  It was a bummer, but as you’ll see, we managed to do SO much in just a day!

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Some overall tips for Tallinn

Here are a few things that are helpful to know if you’re visiting Tallinn, including some observations of my own.  Then further below I go into detail on what to wear to be comfortable walking around all day.

First off, Estonia is really affordable, and was a breath of fresh air from the much more expensive Finland!  This means not only your meals, souvenirs, etc. will be cheaper, but you can get a really nice hotel for a bargain price (see my recos below).  Note, Estonia is on the euro, so you don’t need special currency.

Getting around the city is easy, and for the most part you can walk (at least between the ferry terminal and Old Town).  We also walked from Old Town to Tellisivi District, but then took an Uber back to the ferry terminal vs. 30 minute walk in the dark.

Old Town restaurants are expensive tourist traps, for the most part, so if you have the time and inclination it’s nice to branch out.  The Telliskivi District has good options (I’ll show you a few below).

Amber is huge here, and makes a beautiful souvenir if that’s something you like.  Also, a general observation is that both the Finns and Estonians seem obsessed with cats, so you’ll see cats on tons of souvenirs.  It’s charming and I love it.  I wanted to boop this kitty on the nose!

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What to wear in Tallinn (in winter)

I can’t speak to spring, summer, or fall, but I can tell you that Tallinn felt quite cold when we were there.  Tallinn is considered to have a more temperate climate than other cities at a similar latitude, but it definitely felt colder than Helsinki had the day before.

It was a nice enough day by mid-February standards, but that kind of clear cold with enough wind to really chill the bones over time, and we were outside basically all day.  Generally I’d recommend layers that you can shed if you overheat.

So here’s what I wore, and would recommend:

• Coat:  I brought two coats on this trip, my intense Helly Hansen that I knew I’d need for Lapland, and then a slimmer puffer coat that didn’t take up much space but was still really warm.  I wore the puffer in Tallinn because it was cold but not frigid.  I do recommend having a hood!
• Footwear:  I brought two pairs of boots—real Sorel snow boots (these are lighter weight and cute but still really warm) and more regular walking boots (which worked well since there wasn’t much snow).  I wore the Sorels just to be safe, though I think I could have gotten away with the others.
• Tops:  I had both merino wool thermal tops as well as normal lightweight athletic ones for layering under sweaters.  I brought this cuter merino wool sweater and wore it everywhere, including to Tallinn.
• Bottoms:  I wore both fleece-lined jeans and thicker fleece-lined leggings on this trip…both were cute, and I stayed warm enough.  I ended up wearing the leggings to Tallinn since I’d worn the jeans the day before.  I have a deeper post on my fave fleece-lined leggings for different things.
• Other gear:  This hat was warm, comfy, and cute!  I also used these gloves and brought a neck gaiter just in case.  And wore merino wool socks (these and these were my go-to’s…sometimes I only wore one pair, other times layered).

I have deep-dive posts on visiting Bergen (Norway) in winter (which I’d say was the closest to Tallinn climate-wise) and Iceland, as well as a super Arctic packing list.  I highly recommend reading those posts, especially if you’re visiting other areas on a colder-weather trip, as they have more details.

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Where to stay in Tallinn

As I mentioned above, we had originally planned to have one night in Tallinn but had to scrap it fairly last-minute.  After some research, I’d booked at the Rixwell Collection Savoy Boutique Hotel, which was super centrally-located in Old Town, beautiful, and got awesome reviews.  Plus, SO affordable!

The other few that were on my shortlist were Hotel Telegraaf and Schlössle Hotel, which also look amazing.  These apartments look adorable, as does this “Rapunzel” old tower apartment, if you’re staying more than one night.

Other adventures from this trip that you’ll love:

What To Do In Helsinki: An Itinerary For Finland’s Capital City In Winter

Experiencing a Traditional Finnish Sauna (Löyly Sauna in Helsinki)

Watching The Northern Lights Dance From A Mobile Cabin On A Frozen Finnish Lake

What To Expect Taking The Helsinki-Tallinn Ferry

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What the Helsinki-Tallinn ferry was like

Since we were doing a Tallinn day trip, we made sure to book the earliest ferry (7:30am) from Helsinki, to have a full day to explore.  The ferry terminal we went out of in Helsinki is large and modern, and there weren’t any security checkpoints or anything.

The crossing takes about 2 hours each way and the ferry itself was really nice and absolutely huge, more like a cruise ship.  We took one of the later boats back to Helsinki, around 7:30pm.

One other tip…when you get  back to Helsinki on the ferry, don’t take a taxi from the queue.  It took FOREVER due to traffic, and because it was metered it ended up being way more expensive than Uber.  We had barely made it out of the ferry terminal and the meter was up to €20.  Literally the taxi ride cost what my round-trip ferry ticket to Tallinn cost.

Read more about taking the Helsinki-Tallinn ferry here!

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Things to do in Tallinn (including on a day trip)

We arrived in Tallinn from Helsinki around 9:30am, quickly disembarked (made easier by not having luggage) and started walking the 15 minutes or so toward Old Town.  Boy, we felt the wind more than we had in Helsinki!

About halfway there we found one of the coffee shops on my list, called RØST Bakery…it’s tucked into a little kind of planned apartment community inside these walls.

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RØST is a super cute (and quite tiny) coffee shop and bakery that has won local awards (try a flat white!).

They serve fresh baked goods every day, and you can watch them make the pastries while you wait in line.  Apparently their specialty is a cinnamon twist, but I couldn’t resist these citrus poppyseed swirls—DELISH.

It was packed, so I got mine to-go so we could get to Old Town as quickly as possible.

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Finally the  old city walls of Tallinn came into view!  One thing you can do if you have time is walk the city walls.

There are only a few segments remaining, and you can choose to walk along a section at the Danish King’s Garden (with rooftop views, right by the Kiek in de Kök Museum and Bastion Tunnels), or on the other side of the city is Hellemann Tower and Wall walkway (3 euros to go up here but the rooftop views are supposed to be beautiful).

We sadly didn’t have time for wall walks on this visit, but it would definitely be on my list for next time.

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Explore Tallinn’s Old Town

To orient you, the Old Town is split into two levels.  The upper town is up on a steep limestone hill (called Toompea), and houses governmental buildings, an imposing castle, St. Mary’s Cathedral, and the Russian Orthodox Alexander Nevsky Cathedral.

We’re starting in the lower town that surrounds the base of Toompea, and is a maze of winding medieval streets, pretty pastel buildings, marketplaces, squares, and more.

I was obsessed with the arched entrance of the Great Coastal Gate in lower Old Town (one of a handful scattered around the town walls).  Then we started our way up Pikk Street (a.k.a. Long Street), which is full of shops and bars.

I believe one of the other entrances takes you up Viru Street, which has more contemporary shops but a nice photo op of the old city gates.  We didn’t make it all the way to those gates, unfortunately.

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Much of the historic city center dates from around the 13th century.  It feels a lot like Prague’s famous historic Old Town, but is more of a hidden gem so there are a fraction of the tourists.  It is gaining in popularity, however, as a great European weekend break, and (sadly) becoming popular with stag and hen parties.

I was thoroughly charmed by the pastel colored buildings and hodge-podge of architectural styles.

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I loved finding all the up-close details as well…colorful patterned doors, that beautiful lantern, old historical crests or tiles.

Pikk Street was where the rich merchants and guild were, and you can still admire the 15th-century houses with facades.  One thing I didn’t realize when we were there is that the walls of some buildings have informational signs so you can learn about their history.

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As you get close to Town Hall Square (also called Raekoja Plats), this view of the square from Mundi Street is one of the famous ones in Tallinn.

This tiny pedestrian street perfectly frames the spire there, and in the early winter it also frames the town’s giant Christmas tree perfectly (Tallinn is known for having a great Christmas Market).

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Stop by Town Hall Square

Raekoja Plats (Town Hall Square) is the beating heart of Tallinn, and has been a marketplace and the city’s center since the Middle Ages.  The Gothic-style Town Hall was built in the 1300s and is the oldest surviving one in Northern Europe.

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Between the 13th and 16th centuries, Tallinn (then called Reval) was a major trading outpost (Bergen was another) of the Hanseatic League due its strategic location on the Baltic Sea.

Over the centuries it changed hands several times, from Danes to Teutons to Swedes to Russians, and then spending about 50 years in the Soviet sphere before gaining independence in 1991.

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By this point I was getting chilled to the bone, so found us a delicious bakery for cinnamon buns and glögi (local mulled wine).  It’s non-alcoholic by default (so actually really just mulled juices), and they’ll add a shot of liquor if you want it alcoholic).

Pulla Bakery on Voorimehe Street was a little hidden, but a lovely surprise.  The cinnamon buns here were quite different in style from Finland’s, and I took mine back to the Town Hall Square to munch on.

Then I had to make sure this GIANT seagull didn’t take my food.  Seriously, he was a monster.

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We kept exploring, mostly just wandering up and down streets without specific destinations in mind.

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Visit Alexander Nevsky Cathedral

But then we did want to make sure we got up to the upper town.  There are a lot of beautiful buildings and different architectural styles up here, as this is where the rich merchants used to live.  Now it’s home to embassies and the government buildings.

First stop here was the stunning Alexander Nevsky Cathedral, a Russian Orthodox Church (it’s free to go inside).  The outside is quite ornate but didn’t look that special in the gray, overcast skies.  I’m guessing that it would really POP against blue skies though.

Right across the street from the cathedral is Toompea Castle, which has been the seat of power in Tallinn since the 1200s (and in fact the Estonian Parliament is still here).

This particular building was built in the 1700s on the older fortress, and is an interesting mixture of styles (including this pink Baroque palace, but the other side is medieval castle).

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The inside of Alexander Nevsky is absolutely gorgeous…I’m OBSESSED with these deep teal walls against the gold trim.  The church was built around 1900, dating to the Neo-Byzantine era, and is Tallinn’s tallest and grandest Orthodox cupola.  To me it’s one of the must-do things if you’re visiting Tallinn, even for a day trip.

A couple tips…men must remove their hats inside Russian Orthodox churches, and women ideally should have their head covered.  Also, you’re not supposed to take photos or video inside, which I didn’t realize at first (though selfishly I’m happy I have these, as they’re beautiful).

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From the Orthodox Cathedral, you can head to St. Mary’s Cathedral, a Lutheran church just a square over.  It’s the oldest church in Estonia, originally built in the 1200s as a Roman Catholic cathedral and modified several times over the centuries.

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As we head back downhill toward lower town, I’m in love with this view of the tall tower and sharp spire of St. Olaf Church.  This is pretty much what I picture when I think of Tallinn.  The 124-meter-high tower was the highest in Europe for about a century, and can be seen from all over the city.

This walk down felt a bit magical, with snowflakes swirling.  At the bottom of the hill is the arch called Pikk Jalg (long leg gate), which used to be the only major road connecting both parts of the city.

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Make sure your wanderings take you by the quaint Masters’ Courtyard, a tiny spot tucked off Vene Street.  It’s especially picturesque in the summer, with glossy green vines growing everywhere, but it’s worth a stop any time of year.

We stopped in at Pierre Chocolaterie, a quirky little shop with sweet treats, coffee, glögi, and snacks.  I got some glögi to warm myself up and also took advantage of the restrooms.

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For lunch we decided on Kompressor Pub, which is famous for their coffee and also for”mega filled savoury pancakes”.  I got a delicious local stout and we split some apps, then I couldn’t resist trying both a sweet and savoury pancake (kind of like a thick crepe?).

It was a LOT of food, I couldn’t possibly finish everything…if you’re looking for a filling, affordable meal with locally-sourced ingredients, Kompressor is a great option.

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Soak in the views from one of Tallin’s many viewpoints

There are a ton of scenic views all over the Old Town.  We didn’t get to all of them, but we spent a few minutes at Kohtuotsa Viewing Platform (see the pics below) and would definitely recommend it!  I can’t get enough of these views.

Another well-known one is Patkuli Viewing Platform, and there are also amazing views to be had by climbing some of the church spires and towers around Old Town.

More cool buildings we soaked up as we wandered.

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One spot we tried to visit early in the day but failed at (I think they maybe weren’t open?) was St. Catherine’s Guild.  It has several interlinked craft workshops, where talented local craftspeople make and sell beautiful leatherwork, textiles, glass, ceramics and more.  It’s a great place to find a unique souvenir.

Alongside and connected, St. Catherine’s Passage is a unique medieval alleyway and one of the oldest parts of the city.  You definitely need to know about this alley in advance, as it can be a bit tricky to locate (it took us a few tries!).

The old stone arches are nearly 700 years old and apparently there’s a monastery the same age here.  Some of the craftspeople’s shops are dotted along the passage as well.

We wrap up our Old Town explorations with what I *think* is St. Olaf Church, just from a weirder angle.

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Soak in the colors of Telliskivi Creative City

While we could easily have spent our entire Tallinn day trip in the Old Town, I wanted to make sure we experienced more of the city.  So we trekked about 15 minutes over to Tellisivi Creative City, a former industrial area that’s been transformed into a vibrant creative enclave.

It’s packed with street art, hipster bars and restaurants, pop-up shops, start-up companies, and local designers.

The various styles of street art are a huge draw here, and we spent some time just walking around finding different designs.  The squirrel was a particular fave of mine, in addition to the kitty cat from the very beginning of this post.

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This area is also home to Balti Jamaa, an indoor market with tons of food stalls, clothing shops, and more.  We tried to find it to eat dinner, but Google Maps was being weird.  It’s on the way to Telliskivi.

Instead, we walked into Lendav Taldrik, a modern Indian place with a really great ambiance.  We got gin drinks and some appetizers to begin with, including chicken pakora and meat samosa.  It was enjoyable but the food didn’t completely wow us, so we decided to sample another place for dinner.

We ended up at Koho Restoran, which was great!  We had delicious great sourdough with cumin hummus, my beef tenderloin was good, and their sweet potato fries were great.

Before heading back to the ferry, we made one last stop.  I saw Juniperium as we arrived in Telliskivi, but it wasn’t open yet.  It’s a local gin distillery and cocktail bar.  So YES PLEASE.

The ambiance was cool and my winter signature gin & tonic was delicious (though I regret not trying one of their fun cocktails).  This is a must-stop if you love good cocktails!

But then our time was up and we needed to take our Uber back to the ferry terminal.  I’m pretty impressed with how much we were able to see and do with just a day trip to Tallinn from Helsinki!

There were a handful of things we didn’t get to do at all, including the city wall walk (as previously mentioned.  Another thing was exploring some of the local craft breweries…some recommendations were Hell Hunt, Brewery Õlleklubi, St. Vitus, Põhjala Brewery, and some within Balti Jaama Turg.

Another aspect of Tallinn’s history that’s worth diving into is KGB history.  There’s a KGB museum on the 23rd floor of the Viru Hotel (just outside Old Town).  Additionally, you can visit the KGB prison cells in the Old Town on Pikk Street.  Both of these provide rich opportunities to learn about this terrible time in Estonia’s history.

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