Looks like you've received some enlightening advice from the gals. The thought of you and Roxanne with our Jeannie as tour guide conjours up an interesting picture. Do you think Roxanne is ready for that? Just kidding Jeannie...luv ya hun!
Having visited the city a few times, I can recommend the Freedom Trail walking tour if historical Boston is of interest to you. The Harbour is another must-see place. Lots of things to do and is where you pick up your harbour cruises. The USS Constitution (oldest commissioned US warship) is also worth a visit. For some nice restaurants, head over to Newbury Street. If you make it over there, you`ll see one with the best name ever, Stephanie`s on Newbury. Need I say more.
If you have time to explore the Cape, don`t listen to Jeannie, and head on up to Provincetown. Lots of beautiful, neat, one-of-a-kind stores that will keep Roxanne happy. You may also run into some T-Girls if you`re in need of a CD fix. You can also take a whale watching cruise which was at the top of my list of things to do there. Awesome! There are plenty of things to see along the cape. Stayed in Hyannisport one time, taking in some of the Kennedy history, as well as a ferry ride across to Martha`s Vineyard and Nantucket Islands. Again, well worth the trip.
For your last night in Beantown, you may want to take in Cirque Du Soleil which is in town for a few shows. What Montrealer wouldn`t enjoy that. You can check out the events calendar for some more ideas. http://www.cityofboston.gov/calendar
Best of luck with the planning. Make sure you bring along plenty of romance.
Stephanie