Exploring Tallinn: A Three Day Journey

I’m often asked where one should visit in Estonia. While there is much to explore across the country I will share a three day agenda for Tallinn and the surrounding regions that I often provide to friends visiting the country for the first time.

Day One:

  • Morning: Take an old town tour and then go explore. Make sure to climb all the way up to get the pristine views and explore all the nooks and crannies and winding side streets.

  • Lunch: Stop by Balti Jaama Turg and eat at one of the little shops there.

  • Afternoon: Walk around Telliskivi to enjoy the graffiti art and a stop at Fotografiska. Grab a gelato from La Muu and do some shopping at one of the craft stores in the area.

  • Evening: Dinner at Rataskaevu 16 in the old town and then drinks on the deck at Põhja Konn in Telliskivi. For the more adventurous, enjoy some of the local clubs in the Telliskivi area or check out Peatus, a converted train that becomes a bar in the evening.

Day Two:

  • Morning: Pick up a Bolt rental, pack a picnic, and head to the sunken prison in the flooded Rummu Quarry.

  • Early Afternoon: Take a dip at Rummu, enjoy the art and some lunch, then do a quick hike to the overlook which sports tremendous views (this is one of my favorite memories of Estonia). 

  • Late afternoon: Drive to Paldiski and enjoy a seaside walk before driving back to Tallinn.

  • Evening: Eat a hearty meal at Restoran Pull, which specializes in meat dishes. Walk around the Rotermanni district and enjoy some live music at Chicago (often outdoors in the summer) before heading to Whisper Sister, a speakeasy at the edge of the old town known for its cocktails.

Day Three:

  • Morning: Visit Vabamuu Musuem which details the history of occupation that the country went through. It is a depressing yet critically important stop, both to get a better sense of the history of Estonia but also to understand the mentality which drives the culture even today. 

  • Lunch: Restaurant Salt, just a few minutes away from the old town.

  • Afternoon: Walk through the Rotermanni district, stopping at the local Kalev chocolate shop for some Estonian sweets. Explore the slowly decaying Linnahall which was built for the widely boycotted 1980 Olympics while the country was under Soviet occupation.

  • Evening: Enjoy a stroll through the old town before going to the newish neighborhood of Port Noblessner and visiting restaurant 180 for dinner and to enjoy the sea views.