Tallinn’s Old Town is compact and can be fully explored in two days. On the third day, head to Lahemaa National Park, and use the fourth day for Baltic Sea views and shopping—no hotel changes required.
In the morning, enter the Old Town through Viru Gate: visit the Town Hall Square, Europe’s oldest pharmacy at the Town Hall, admire the wood carvings in St. Olaf’s Church, and browse the artisan shops in the Masters’ Courtyard. In the afternoon, climb Toompea Hill: see Toompea Castle (now home to Parliament), the onion domes of Alexander Nevsky Cathedral, and the Kohtuotsa and Patkuli viewpoints for panoramic views of the red-tiled rooftops and the Gulf of Finland. For dinner, try a medieval-style restaurant in the Old Town, sampling wild boar stew and honey beer.
In the morning, visit the Seaplane Harbour Maritime Museum to see the icebreaker Suur Tõll and the century-old submarine Lembit. Have lunch at the rooftop café of Hotel Cavalieri, and stop by the five-floor KGB Museum (don’t miss the radio surveillance room). In the afternoon, walk or take the tram to the Telliskivi Creative City: explore the F-Station flea market, factory galleries, and the Baltic Sea promenade. End the evening with photos in the Kalamaja wooden house district and experience an Estonian sauna.
Join a day tour from Tallinn to Lahemaa (or take a bus and drive yourself): hike through the morning mist along the Viru Bog boardwalk, visit Palmse Manor and its waterfall, and have lunch in Altja Fishing Village (try smoked eel with rye bread). Return to Tallinn before sunset. In winter, opt for a tour featuring frozen waterfalls and snow hikes.
Start with Kadriorg Palace (Baroque palace and the Art Museum of Estonia) → Song Festival Grounds (iconic site for mass singing events) → Pirita Beach and monastery ruins → shop for rye bread, kama flour, and handmade sweaters in the Old Town, then depart from the airport or port.