The UNESCO-listed medieval core inside the city walls, dense with medieval taverns, modern bistros and the highest concentration of Michelin-listed kitchens.
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.
Signature: Estonian small producer menu, Game course
Order: Order from the short seasonal menu; the kitchen names its farms and foragers.
Tip: Old Town room with a deep wine cellar. Was previously called Leib; the brasserie reopened as Lee.
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.
Signature: French-Russian classics, Estonian seasonal mains
Order: The tasting menu paired with Champagne from the long list.
Tip: Sunday brunch and afternoon tea also served. Live music most evenings under a glass-roofed atrium.
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.
Signature: Braised elk roast, Beef tenderloin with savoy cabbage
Order: Braised elk roast with potato and beetroot gratin.
Tip: Book a week ahead in summer. The Väike Rataskaevu sister room on Niguliste 6 runs a smaller evening menu.
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.
Signature: Hand-rolled pasta, Italian sharing plates
Order: Whatever pasta is on; the menu is short, seasonal and Italian-leaning.
Tip: Previously called Cru. The hotel above runs the same name; the restaurant relaunched as Osteria il Cru in 2024.
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.
Signature: Dirty steak, Low-temperature beef
Order: The dirty steak cooked in the coals; or the low-temperature beef tenderloin.
Tip: Closed Sundays. Entrance is from Tornimäe street side. Lepik is a past President of the Estonian Chefs Association.
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.
Signature: Daily seasonal mains, Baltic fish course
Order: Whatever the daily menu sends; the kitchen leans on Estonian fish and seasonal vegetables.
Tip: Closed Sundays. The basement seating is the calmer of the two rooms.
Rataskaevu 16 is the Old Town's mid-priced Estonian comfort-food room, with braised elk, beef tenderloin and chef's choice white fish on a dietary menu.
Signature: Braised elk roast, Beef tenderloin
Order: Braised elk roast with potato and beetroot gratin (€28.60); add the Estonian cheese platter.
Tip: Book a week ahead in summer. Sister room Väike Rataskaevu at Niguliste 6 takes the overflow with a smaller menu.
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.
Signature: Smaller-portion Estonian plates, Game course
Order: Whatever the night's seasonal main is; the menu is shorter than the parent room.
Tip: Saturday lunch only, otherwise dinner. Useful when Rataskaevu 16 is full.
Osteria il Cru on Viru is the Old Town's reliable mid-priced Italian, with hand-rolled pasta and an olive tree inside the dining room basement floor.
Signature: Hand-rolled pasta, Italian sharing plates
Order: Whatever pasta is on the daily menu; the wine list runs deep on Italian regions.
Tip: Closing times shift in autumn-winter. Was formerly Cru; relaunched as Osteria il Cru in 2024.
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.
Signature: Grand Chef's Feast, Bear and elk plates
Order: The Grand Chef's Feast tasting; the kitchen runs an entirely candle-lit, electricity-free dining service.
Tip: Live medieval music Wed-Sat 18:00-21:00. Three floors plus a cellar, but the room books out for the feast nightly.
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.
Signature: Elk soup, Savoury pirukad pastries
Order: Elk soup and a couple of savoury pirukad; pickles come from a wooden barrel at the bar.
Tip: Staff stay in medieval costume and play brusque innkeeper. Cash and card both accepted; servings cost a couple of euros each.
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.
Signature: Daily seasonal mains, Modern European plates
Order: Whatever the seasonal daily menu sends; the kitchen runs a vegetarian-friendly room with full vegan options.
Tip: Vintage Pegasus interior preserves the Soviet-era ceiling. Window tables look across Vabaduse square.
Härg on Maakri is a Michelin-listed grill room run by chef Taigo Lepik, with low-temperature beef and a dirty steak cooked directly in charcoal at the bar.
Signature: Dirty steak, Grilled lamb
Order: The dirty steak from the coals; or the low-temperature beef tenderloin.
Tip: Closed Sundays. Sister room Pull at Rotermanni 2 runs the same grill discipline.
Tallinn Old Town Days each June fills the medieval centre with around 300 events plus pop-up food stands, historic cellar cafes, smoked fish.
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 on Town Hall Square runs late November through early January, with verivorst, hapukapsas and gluhwine huts under the medieval.