Don't stay at the Boston Harbor Hotel. Stay only at the Ritz or Four Seasons. I say this b/c of location only. The Harbor is terrific, but not if you want to explore the city with ease. The Ritz and Four Seasons is terrific. I prefer the Ritz, myself. The location can't be beat. Brunch at the Claremont Cafe in the South End is fabulous. The gondola ride is a must, as well. Good luck.

Cee Cee are you referring to the old Ritz or the new Ritz?

Blew your cover, sorry not a travel writer. The money was given to us by a donor that contributes heavily to this auction each year. Last year it was a roundtrip flight on his Lear Jet from Boston to New York, a night at one of the Helmsley hotels, tickets to "The Producers" and dinner at a restaurant. That package went for $2500 last year. Because some people are still concerned about flying and security, we came up with the idea of a fantasy weekend in Boston, and this is how we are putting the money to use.

And, yes, you are correct that many hotels will donate rooms. In fact, I've written to all of the 3 and 4 star hotels in Boston and Cambridge -- there are 33 of them. Fifteen have already donated rooms for either a 1 night or 2 night stay. I've been turned down by 5 and still have not heard from 13. I have also received numerous gift certificates for restaurants. However, these items will be auctioned off separately on a silent auction, along with the many other items that have been donated.

At the moment the Lenox is entirely covered in scaffolding which is not only ugly but probably means lots of noise for the guests. I think they are redoing the brick work.
I also would steer clear of the Bay Tower room. No offense for this generalization but if you have ever been in the lobby and seen the people going upstairs the words "luxury" and "class" don't come to mind. Hammersely, Aujord'hui or Icarus are good ideas for dinner. I would throw in the spa treatment too. There are plenty of men at Bella Sante. If the couple is staying at the Four Seasons, Candela is right there too.