Welcome to CF!
I live outside of Boston and sailed out
Hull at the south end of Boston Harbor for many years. We've moved our base to
Rhode Island which has been great, but not better than Boston Harbor.
You mention "getting into" sailing. I'm going to infer that that means that you and your wife are planning to learn. Boston has a couple of excellent ways to learn sailing without breaking the bank. If you're completely new to the activity, Community Boating on the Charles River is a good way to learn the basics in small boats. If you're beyond that (or once you're beyond that), the Boston Harbor Sailing Club
Boston Sailing - Schools Lessons Certifications - Boston Harbor Sailing Club - Sailboat Racing Moorings Rentals Charters has a range of cruising boats that members use for
day sailing out into
Massachusetts Bay and chartering for longer trips. Many years ago, my (not yet) wife made the transition from
crewing for her Dad to sailing her own
boat at BHSC and still has friends from the experience. If you live in Boston, the sailing is close enough that weekday summer evenings are a viable option for lessons and short
sails.
The Boston Harbor Islands are a well kept secret since Boston Harbor was once best know for its well-named "Dirty Water" by the Standells. Thanks to massive cleanup, it's now a great place to sail and swim (if you like the cold temperature).
Once you're out on your own, there are excellent cruising grounds from
Maine to Block Island that are extremely varied and have kept coastal sailors engaged for a lifetime.