The Old Town is the heart of Tallinn’s social sector and while it’s small, it’s got countless pubs and clubs crammed into it, plus the obligatory strip clubs. Tallinn has a huge student population so the atmosphere is raucous but friendly – more importantly the women are beautiful.
If you have any energy left after the first night, Tallinn is a beautiful city to stroll around during the day – stay close to the Old Town as Soviet-era architecture tends to dominate outside the main tourist areas. Bars and cafés line the Town Hall Square (Raekoja Plats) which is a great place to sit in the sun and watch the world go by. The beautiful network of parks are well worth a visit and Tallinn’s excellent zoo can provide hours of easy entertainment for a hungover Stag party. For a fun way to see the city try the Tallinn Chill Out Walking Tour, which takes you on a leisurely walk around the city with a crazy musician as your guide.
If you are going to be doing a lot of sightseeing be sure to pick up a ‘Tallinn Card’ for everyone from the tourist office, this gives the holder free local public transport and entry to most attractions.