Tallinn, Estonia ~ making friends!

*This blog contains affiliate partnerships. Every little bit (and I mean little) helps me continue to provide free travel tips and advice. Thank you for supporting ©Travel with Wendy.

Parts of the wall in Tallinn

It was over ten years ago when Rick Steve’s introduced the world to Tallinn, Estonia. But they have been around a little bit longer than that. I have to say Tallinn, Estonia is an absolute keeper for me. I am so excited to share about this destination and so excited to return, we made friends everywhere we went.

This past fall Jon and I had uber cheap tickets to Tallinn in November. Yes, I know this is not the ideal weather to travel to the this part of the world, however, I NEVER let weather indicate an opportunity to travel. If I did, I would always stay at home. Most of Europe is covered in a gray cloud beginning in October and ending in March. So off we went.

Tallinn - ancient walls

Over 80% of Tallinn was preserved during WWII, so to me, it was in medieval “mint” condition. I truly felt like we were walking the streets of the 15-1600’s a lot of the time.

How did we get there?

Green girl!

Lufthansa had a great flight out of Stuttgart (with an hour layover in Frankfurt) to Tallinn for €120 RT for both of us. Yup ~ super cool. The ease of taking the train to the airport, arriving early to check-in and then take our time was wonderful. I do love flying out of Stuttgart if it is available and affordable.

Our flight from Stuttgart left early – 8:45 a.m. so plenty of time to get there, checked-in (the very first time, I was the very first in T2 (Terminal 2) at the airport. I felt super special. HA! We had enough time to grab a coffee and a pastry, check e-mail then begin boarding.

Static 1 - Post Rebrand

Some people arrive for “domestic” flights just an hour before departure. I don’t like this tight of a window, so I recommend arriving at least 2 hours before, you can always grab your laptop or iPad and get a little work done.


Old House Apartments ~ apartment with a sauna
In this region of the world, you’ll want to look for accommodations that have saunas. Yes, it is that cold. Besides, when they are in your room, BONUS! We did have to have a “Dummie’s guide to turn on your sauna” moment with the housekeeper. That was special. Our room at the Old House Apartments was just gorgeous, fitted with a kitchen, living area, and a huge bed. The vaulted ceilings and exposed timber beams just added to the “old world” charm and excitement of this medieval town.

I wrote an email to the owner that we would be coming in later in the evening and she recommended a cab from the airport. It was under €15. This area of the old town has some crazy one way streets and I heard murmurs that they may be trying to make it “pedestrian-only.” I kind of agree it would enhance the area tremendously.


We met Andrus the owner who was super sweet and if you book directly your rate would be better. Our location was perfect we were within walking distance of everything and it was nice to be refreshingly car-free.

Hestia Hotel Barons ~ elegant old hotel in the heart of the city

Hestia Hotel Barons

We hopped over to Helsinki, Finland for a few days and then returned to Tallinn before flying out. We stayed at the Hestia Hotel Barons in old town, Tallinn. I LOVED this place too, we felt like we stepped back in time to the 1920s and ’30s. From the rotating door at the entrance to the gabled ceilings, old rounded staircase, and glass-paned elevator, I felt like I was in a movie-set.

Hestia Hotel Baron - Entrance - Tallinn

We arranged for “a car” to pick us up from the ferry, I know, super snazzy. Not really, it was the same as a taxi, but I felt posh for a second.

We stayed in a Baron Suite (it really wasn’t that expensive) about €100/night in November. This included our breakfast which was yummy, had plenty of crunchy bacon and scrambled eggs too.

Room fit for a Baron

It’s a very quiet hotel, but it is close to the bar district, so if you stay on a Friday or Saturday night expect a little late night chatter. Unless, you like to party and then the partiers will probably ask you to join them.

Medieval Tours & More…

This past year I had a few friends visit Tallinn and recommended a few things.

  1. Take a tour with Tales of Reval

So before we even left I sent an email requesting a private tour of the city. I ALWAYS ask for a private tour if possible so I can get the most information to share with you. Typically, they are not too expensive and totally worth it to have undivided attention. If you travel with a small group it may be worth asking – especially if you have someone who asks “lots of questions!”

Happy Cedric

We became quick friends with our guide, Cedric. We had so much fun and after our tour, he introduced us to some of his friends, George and Michael who were a hoot too! They took us to a medieval pub in the old courthouse basement. This was hysterical cause the “bar wench” was gruff and quick with a joke and made me a laugh. We chatted for quite some time about the history of Tallinn, tourism and what’s ahead. Super nice company and very informative group ~

2. Eat at Café Moon (see below)

This amazing restaurant will blow your mind with the dishes they prepare! YUM~

3. Shop the Central Market

Central Market

This local market is filled with clothing, restaurants, fresh food, trinkets and much, much more! For those shoppers out there, leave space in your carry-on for purchases here – it is a “locals” favorite and easy to get to ~ Keskturg
4. Visit the Depeche Mode Bar!

This was a happened-upon bar as we were walking the medieval streets of Tallinn, fellow tourists said, “Hey, do you like the 80’s?” Ugh…. wanna see my jelly shoes? Of course, and led us to the Depeche Mode bar. I know, right! I was in 7th heaven. Cozy bar with a sleek, retro feeling. It made me feel like I was 17 again.

Push Pin Travel Maps


Good EatsGood EATS!

Be prepared for some really GREAT food in Tallinn. If you are a meat and three kinda guy or are traveling with one, this is the town for YOU! We tried quite a few places but our favorite was the Olde Hansa.

Recommended by our friends from Reval we hopped on over there and bumped into George. Hard-working young people, I love it. This authentic brewpub with meals that feed you like you are a beast at a feast is super fun. You may feel a bit out of place with your street clothes but the waitstaff never broke character making it a super fun experience.

Café Moon

Another favorite was Café Moon – this exceptional “Foodie” restaurant near the harbor will have your tummy growling just reading the on-line menu. This was recommended by a friend who knows I am partial to ‘really great food.” I didn’t think it was too pricey for the portions and the level of expertise in cooking. MAKE RESERVATIONS though and they close like they have a family on Sunday nights, I totally respect that ~

Our waitstaff and bartender were incredible and anticipated our wants before we even ordered. That was super cool.

Eggplant parmigiana at Cafe Moon

Another fun restaurant we tried was the Mini Burger Factory. This really cool concept burger pub pairs mini-burgers with micro-brews. We thought we would give it a try. The burgers came in several different flavors as well as the paired beer. The service was attentive, however, I think they might have to still work out some rhythms of service, we got our onion rings way before our drinks and burgers, so it was just off a bit, but it seems like a new restaurant and the atmosphere is really cool.

Indeed, here’s another keeper – I know, just own the weight gain! You’ll work it off after the trip. We made reservations at Oliver Restaurant this was within walking distance of the Old House Apartments where we stayed the first leg of the trip, we were now familiar with the old town. Everything we tried here was so delicious. You may see quite a few advertisements for the Oliver Restaurant around town and this might make you think it is a “tourist trap.” You would be wrong. Try it – excellent wine list and desserts too.

~ Gotta go back ~

Also, I gotta be honest, I have heard people say, oh, you can do Tallinn in a day or two, well to that I would say, that’s just silly. Truly, take your time, see as much as you can, make new friends, you won’t regret it. I wish we would’ve spent more time here and I am so looking forward to a return trip to say “Tere” (Hello) to my friends.

Medieval walls of Tallinn

It’s always an adventure when you ©Travel with Wendy!


Push Pin Travel Maps

One thought on “Tallinn, Estonia ~ making friends!

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: