You could also spend your evening going the opposite direction. If you're looking for luxury, start with a gourmet dinner at the MICHELIN-starred NOA Chef's Hall in Pirita. Otherwise, a picnic on the beach with ice cream for dessert is a summertime standard. From there, walk along the promenade before heading back into Old Town for a latenight wander.
Steam the night away in a sauna
Sauna is an essential part of Estonian culture, no matter the weather. Try out the oldest sauna in Tallinn or head out of the city center to a local favorite, the Elamus Spa in Mustamäe. Open until 11 pm, they often feature DJs on the weekends. Iglupark Saunas in Noblessner are one of the city's chicest saunas in a prime seaside location. If you like your sauna with a side of stand-up, then Heldeke is the spot for you. They have a full calendar of comedy, burlesque, and live music. Many of the shows are in English, making it a good stop for visitors willing to venture off the beaten path.
Seek out new experiences around town
At the crossroads between Old Town, the port, and Viru Square, the Rotermann Quarter area has been completely renovated in recent years. Now you can find topnotch restaurants such as Pull or R14 tucked away in the narrow pedestrian walkways. Chicago 1933 is also a favorite for live music and its summertime terrace.
Nearby the aforementioned Iglupark Saunas, you have one of the newest summertime hangouts in Tallinn. The steps next to the marina are great for people watching and grabbing a drink. Noblessner is also home to one of Tallinn's top restaurants, the MICHELIN-starred Restaurant 180° by Matthias Diether.
From Balti Jaam market, head on over to the hipster hotspot, Telliskivi. On the way you can stop by Sveta Bar or Peatus for a drink. Telliskivi is lively in the evenings with a number of restaurants and bars featuring outdoor terraces and venues for live music. For something a bit fancier, try Fotografiska and their rooftop bar and restaurant.