The main branch of the Boston Public Library is a strange beast: half 19th-century McKim masterpiece, half modern mishmash (a recent, and massive, renovation has finally brought the 1970s-era wing into the 21st century). Get the deets during a complimentary hour-long architectural tour, then return for a guide through the library’s surprisingly robust art collection.
One by one, our city’s observation decks have disappeared -- except for one. Right on the Harbor Walkway is a semi-hidden, 14th-floor deck that gives you terrific views of the harbor and the surrounding buildings. Bring your binoculars and your ID (you can’t go up without it), and you can check out the Harbor Islands and watch planes land at Logan Airport. This also happens to be a great cheap date idea if you're out and about with someone sweet.
Boston is no Denver, but there are still a couple of mountains to climb. Just a few minutes outside of the city proper is a 7,000-acre reservation with 125 miles of resplendent hiking trails. Climb Great Blue Hill and you earn an unmatched view of the city skyline, with far fewer crowds in the off-season months.
This was our city’s first hipster chocolate, and one that has since gone national. A tour of the 17,000-square-foot facility give you a primer on stone ground chocolate, including the grinding room and the cocoa nibs from Mexico from which the chocolates are made. The factory store is where the free samples come in.