Tallinn is certainly worth two days. I am a retired, slow traveler, and I spent 11 days in Tallinn in 2023. These are some of the places in Old Town I had on my list of sightseeing targets, organized semi-geographically rather than in priority order:
Vanalinn (Old Town) Well-preserved medieval center with cobblestoned lanes, gabled houses, historic churches, and turreted city walls (most picturesque on west side) with 26 watchtowers. Upper (Toompea) and Lower sections. Mobbed by cruisers from mid-morning. Pickpockets.
Toompea (Upper Town): Fabulous views of Lower Town. Most atmospheric approach through gate at foot of Pikk jalg.
Aleksander Nevski Katedraal (Russian Orthodox Cathedral)
Danish King’s Garden has great view of Lower Town.
Toompea Loss (Castle): Art and craft exhibitions
Piiskopi, Kohtuotsa and Patkuli viewing platforms have good views. Patkuli probably less crowded.
Tallinna Puha Neitsi Maarja Piiskoplik Toomkirik (St. Mary’s Cathedral, Dome Church) and Tower: Gothic; rebuilt after 1684 fire. Sometimes has concerts.
Ruutelkonna hoone (Knight’s House): 19C Neo-Renaissance.
Lower Town part of Old Town
- Okupatsioonide Muuseum (Vabamu Museum of Occupations and Freedom), Toompea tanav 8: Translated printed explanation better than audio guide. Seven 30-min. videos. Excellent introduction to Estonia's 20th-century history.
- Kiek in de Kok Tower, Komandandi 2: Views; current exhibits unclear. I skipped this.
- Neitsitorn (Maiden Tower): Good views; exhibits so-so.
- Tallinn Art Hall
- Tallinn Art Hall Free Gallery
- Adamson-Ericu Muuseum: Art and decorative-art museum, branch of Art Museum of Estonia; incl. ceramics, jewelry, textiles and furniture
- Niguliste Muuseum (St. Nicholas Church): Gothic ecclesiastical art in restored Gothic church
- Linnamuuseum (Fotomuuseum): Photography
- Tallinna Raekoda (Town Hall) and Tower: 15C Gothic building with history museum
- Raekoja Plats: gorgeous square.
- Disaini- ja Arhitektuurigalerie: Exhibition of Estonian product design.
- Viru Gate: Picturesque access point to Old Town.
- Dominiiklaste Kloosti Muuseum: Extensive collection of medieval and Renaissance stone-carving.
- Katariina kaik (St. Catherine’s Passageway): Medieval alley with artisans. Connects Vene and Muurivahe streets near Viru Gate.
- Puhavaimu Kirik (Holy Spirit Church): 13C; splendidly preserved with medieval and Renaissance features
- Eesti Ajaloomuuseum (Museum of Estonian History), Suurgildi Hoone (Great Guild Building): High-tech exhibits and videos
- Pikk Street and Lai Street lined with interesting period buildings.
- Issandamuutmise Kirik (Ch of the Transfiguration of Our Lord): Extraordinary iconostasis. Hours unknown. www.teelistekirikud.ekn.ee
- Tarbekunsti- ja Disainimuuseum (Museum of Applied Art and Design), in courtyard behind Lai tanav 17: Includes textiles, jewelry, glass and 18C-20C ceramics. Impressive collection.
- Kolm Ode (Three Sisters), Pikk 71, just beyond Oleviste Kirik. Three multicolored 14C merchants’ houses, beautifully renovated, now hotel.
- Meremuuseum (Marittime Museum), Fat Margaret Tower: Good reviews, but I skipped this. Great views from top of tower.
- Paks Margareeta (Fat Margaret Tower)kk 70: Houses Meremuuseum. Gorgeous views from top of tower.
I'll put the sights outside Old Town in a separate post.