I'm a professional working out of the Boston area who has recently married and now living with my wife in the City. This means I've transitioned my third floor living area / home office into a private suite for guests. I would describe myself as pretty laid back and enjoy traveling- you can find me at a local coffee shop of any new city I visit (you can tell so much by how they serve their best Espresso). My wife is a bargain hunter- she's all about saving money and finding "good deals." Together, we enjoy the adventure of eating at "hole-in-the-wall" delicious joints- so if you want some great restaurant recommendations please don't hesitate to ask!
I've lived in Boston all of my life and love the history and character the City has to offer. I always recommend that those visiting get to the know the area by foot- the Freedom Trail gives a great free self-guided tour; yes- the tour is complete with a walk through the North End and you can see Paul Revere's house... but it can be hard to make it there without stopping to eat at the many great restaurants in the North End (Mike's Pastries is one to put on your list).
For couples- you can enjoy long walks in the Public Gardens and along Commonwealth Avenue (Guys: the Public Gardens is one of the best places to propose- you can't go wrong here- trust me).
In the Fall/Winter- if you are ready to bundle up a bit- you can do the walk around the Charles River along Memorial Drive / Storrow Drive and enjoy some amazing views of Boston from Cambridge and also venture on over to the MIT Campus. There's plenty of indoor activities such as the Museum of Fine Arts, Isabella Stewart Gardner Museum and the Museum of Science. The Boston Public Library is free and has amazing outdoor/indoor architecture and a few smaller exhibits. Plus, there are a lot of comedy shows and plays that can also be affordable if you plan ahead (check out The Wilbur Theater).
Last but not least- my wife always seems to find herself talking about her favorite bargain shopping- sure Newbury Street has some great finds- but she swears the Cambridgside Galleria Mall (along the Green Line) has some of the best bargains along with the Copley Mall (note- from my wife: no taxes on clothes shopping under $100).