A small group of us will be visiting Boston September 10th to 13th for an all woman fun getaway weekend. We will be staying at the Lenox Hotel in the Back Bay Area.
Would you recommend that we do the Trolley Tour or the Boat Tour on the Charles River?
And we are open to restaurant suggestions in our hotel area, as well as the North End.

Have you been to Boston before? If you are already familiar with the city and its neighborhoods/history/landmarks, then I would skip the duck or trolley tour. If you are fairly new to the city or unfamiliar with it, however, I think it would be a great way to see a lot fairly quickly and get a good feel for Boston.

As for dining... what kind of atmosphere, price range, or food would you like?
Top of the Hub is great with amazing views of the city from above... but very pricey. Reservations probably needed, too.
Summer Shack will have some good seafood dishes and will be priced better... and you can get to Legal Seafoods too, which is basically a Boston landmark in itself (although it has become a national chain, and I personally prefer McCormick & Schmick's seafood over theirs).
In the North End you also have very nice and pricey dining right down to ultra-casual. Prezza is highly recommended, but I also love Pizzeria Regina which has amazing pizza and has been a deeply loved Boston institution for ages... yet it is as casual as casual can get and cheap.

You are coming here at a great time, though, and I think you will love your visit no matter what you end up choosing. =)

Will definitely second the suggestions of Prezza and Pizzeria Regina (for the latter, choose the original location on Thacher Street in the North End, as the satellite take-out outposts aren't nearly as good).

Top of the Hub is worthwhile only if a big long-distance view is a must with your food. Unfortunately, I've found the prices very high, service spotty, and food hit-or-miss there.

There are several much better options for seafood than Summer Shack, in my experience -- the food there is expensive and often sub-par, plus the place is as noisy as an airplane hanger. Am also not a big fan of McCormick and Schmick's -- one can do better in town. Much better seafood options would include:

downscale, sit-down: Dolphin Seafood (Cambridge, near Harvard Square).

downscale, clam shack style: Yankee Lobster (Boston Waterfront area, but alas, no view).

medium to upper scale, sit-down: Neptune Oyster (North End Boston), East Coast Grill (Inman Square Cambridge), some branches of Legal Seafood (main ones to avoid are the ones at Prudential Center Boston and Kendall Square Cambridge), Kingfish Hall (Faneuil Hall Boston), B&G Oysters (South End Boston).

Also avoid any entreaties to eat at Barking Crab and Union Oyster House (do the latter only for raw oysters and beer at the bar). And if you brave the No Name, stick to chowder and fried seafood, as anything fancier than this can result in disappointment.

Boston is very well covered here. A board search is recommended, especially for North End restaurants.

Dear Shandy and Bachslunch,
Thank you for your invaluable input. We are on a "middle of the road" budget, and your suggestions will serve us well.
This will be my first visit to Boston, and I am eagerly looking forward to it.
Everyone has told us to visit Cheers. Would it be worth our while to have lunch there?

Re Cheers: I wouldn't bother with the food there, as it's routine pub grub. A brief stop-by at the original location, just to marvel at how little the real thing resembles the TV show set, is about all one needs to devote here. The branch at Faneuil Hall looks more like the TV show set, but the food's no better.

The most visited tourist site in Boston is Bull and Finch/Cheers. I understand - the TV show was so popular - but it is just a bar with bad food. But it is probably the first thing anyone will ask if you saw when you get home.

If any of you are into food or cooking consider taking the North End Market Tour. One of the trolley tours is a good orientation to the city if you are not a guide book/ride the subway type tourer - and also good in small groups who can't get together to decide what/where to go.

There are an assortment of Harbor cruises - length, location, time of day - that might be interesting for your group.

If you want to stop by "Cheers," figure it in to a leisurely walk around Beacon Hill, to see small townhouses, classic antique glass window panes, cobblestones, and - if you can find your way there on the map - Louisberg Sq. It's a gorgeous, intriguing walk. (Gen'l direx: Walk up Charles St. away from the Garden, Louisberg Sq. is between Mt. Vernon and Pinckney which are perpendicular to Charles.... but get lost in the little alleys along the way, too.)

Right around the corner from bull and finch, you'll find The Upper Crust. EXCELLENT thin crust pizza with fresh, quality ingredients. In the North End, visit Massamino's for sauce like my nanny used to make. Across the street from city hall, is the Kinsale Pub where you'll find great Irish grub. Go to the Black Rose Pub near Fanueil Hall for Irish music. If you like beer, do the free tasting at Harpoon Brewery or the $2 one at Sam Adams. A tour of Fenway Park is always fun if you have any interest in baseball. You'll have a blast, Boston is a great city!

I recently spent a weekend in Boston and took a bus tour which included a second day and a harbor cruise, which was worth the view. I had walked a lot the first morning and realized I couldn't see everything. It was $36 for the two days, this could have been a special because I was there in April. In any event, the bus went over to Cambridge where I transferred and caught a smaller bus over to Harvard Square. It was a great vantage point in which to see the city. You can also get on and off as much as you want.

It's a good way to see a lot of the city and you can always go back to a spot of interest.

I recently took a duck tour for the first time in Boston although I have lived in Massachusetts for decades. It was a blast. Could be because the duck was driven by a friend of ours and was filled with people we knew on the weekend of our daughter's wedding. But if all the drivers are as entertaining as our friend (who drives under the name Johnny Bagadonuts), it would be a great idea for a women's getaway weekend.