Not having planned on visiting Estonia, I stepped off the ferry without expectation. After only a few minutes I could tell that I was going to love this city – it just had a good vibe to it.

The ferry staff had provide me with a city map and the names of a few hostels, so I set off in the direction of Old Town…or so I thought.

After about an hour of walking I seemed to have made no progress toward my destination. It was as if the map and physical streets were conspiring to make me utterly and hopelessly lost.


When I finally stopped to ask someone where I was, they were unable to show me on the map as I’d walked myself right off of it. Luckily, I had ditched my large pack in Finland and only had a day bag because as it turned out, the compass on the map had been printed upside-down and the map itself was dated about four years (thanks ferry lady!)

However, this snafu didn’t bother me a bit. It was a gorgeous day; the sun was out and it was warm (I didn’t even need a jacket!)With my bearings corrected, I had no problem locating the Dancing Eesti Hostel in Old Town. I’m actually rather pleased that the map was incorrect – otherwise I might never have seen so much of the city.

Some streets were lined with stately and established homes, with a flare of elegance that could be found in any upper-class community in the US. Certainly, not all of the neighborhoods were this way; many were aging and run-down with graffiti lining the walls. But they had character and spunk and you could tell that people actually lived there.

As opposed to Old Town. Locals call this place “The Island” or “ Tallinn Disney” because its kept unnaturally clean and nearly every other storefront is a souvenir shop.

Its also about the only place in town to find “Authentic Estonia Cuisine” restaurants as most Estonians eat international fare when they dine out.

As a result, Old Town felt a bit contrived. That being said, it’s a very pretty area with medieval architecture and is the setting for the formation and history of the entire country. I got the sense that even though locals may not live there (they do go there to drink at all the new pubs though) they are extremely proud of what it represents for Estonia.

Outside of Old Town, the business district was (to me) surprisingly modern. On a whole, the people were very kind, proud of their independence (their first post-occupation president was only elected in 1992) and eager to share their culture with visitors.