The UNESCO-listed medieval core inside the city walls, dense with medieval taverns, modern bistros and the highest concentration of Michelin-listed kitchens.
Order Order from the short seasonal menu; the kitchen names its farms and foragers.
Lee Brasserie on Uus is sommelier Kristjan Peäske and chef Janno Lepik's Michelin-listed Old Town brasserie with a long international wine list now.
Order The tasting menu paired with Champagne from the long list.
Tchaikovsky sits inside the five-star Hotel Telegraaf on Vene in the Old Town,a Michelin-listed room run by executive chef Denis Golik with French technique.
Order Braised elk roast with potato and beetroot gratin.
Rataskaevu 16 in the Old Town is a long-running Estonian comfort-food institution, with braised elk roast and chef's choice white fish carrying a vegetable.
Order Whatever pasta is on; the menu is short, seasonal and Italian-leaning.
Osteria il Cru in the oldest building on Viru is a Michelin-listed Italian room with an olive tree in the small Old Town hotel dining area now.
Order The dirty steak cooked in the coals; or the low-temperature beef tenderloin.
Härg on Maakri is grill master Enn Tobreluts's Michelin-listed grill room led by chef Taigo Lepik, with low-temperature beef and a dirty steak cooked.
Order Whatever the daily menu sends; the kitchen leans on Estonian fish and seasonal vegetables.
Rado on Vene in the Old Town is a Michelin-listed modern Estonian room with a daily-changing seasonal menu and a stylish split-level basement floor.
Order Whatever the night's seasonal main is; the menu is shorter than the parent room.
Väike Rataskaevu on Niguliste is the small-format sister to Rataskaevu 16, serving a tighter dinner-only Estonian menu two streets away in the Old Town.
Order The Grand Chef's Feast tasting; the kitchen runs an entirely candle-lit, electricity-free dining service.
Olde Hansa on Vana turg in the Old Town is a long-running Hanseatic-feast restaurant with medieval costumes, live hurdy-gurdy music and a 14th-century menu.
Order Elk soup and a couple of savoury pirukad; pickles come from a wooden barrel at the bar.
III Draakon under the 13th-century Town Hall on Raekoja plats is a tiny medieval-themed tavern serving elk soup, pirukad pastries and house beer cellar.
Order Whatever the seasonal daily menu sends; the kitchen runs a vegetarian-friendly room with full vegan options.
Pegasus on Harju has been a Tallinn dining-room landmark since 1962, with three floors of modern European cooking and Harju Hill views above the Old Town.
Also on this listRataskaevu 16Osteria il CruHärg
Tallinn Old Town Days, held since 1982, fills the medieval centre each June with about 300 concerts, street theatre, fairs and tours across three days; 2026 ran 5 to 7 June.
Tallinn Coffee Festival each April gathers Baltic and European specialty roasters at the Kultuurikatel Creative Hub, with cuppings, latte art and barista.
Tallinn Craft Beer Weekend, organised by Põhjala Brewery at Kultuurikatel since 2015, runs a buffet-style tasting of 370 beers from international breweries.
Tallinn Christmas Market opens on Town Hall Square on 20 November for the 26th time, around what it calls the world's first public Christmas tree.
