At top of the Prudential building in Back Bay - awesome views, a fun place to hang for a drink.
Dana used to give the Beacon Hill walking tour. Any of the tours are a great way to explore the city and learn some cool history and trivia.
Dana used to give the Art and Architeture tour here. The free tour is Friday and Saturday at 11:00am. Even if you can't take the tour, pop in. It's a stunning space. You'll also find a quiet hidden courtyard for hanging out with a beverage. There's a cafe and if it's your thing, make a reservation for afternoon tea - it's delish and the tea room has a beautiful vibe.
Highly recommend a stroll here and perhaps a ride on the Swan Boats.