We have a family wedding in Manchester by the Sea the first week of June and we are planning to make a vacation out of it since the kids and I have never been to Boston. We will be in the area about 7-8 days. Our daughters are 15 and 12. I am looking for recommendations for:

1) The must-see attractions in and around Boston;
2) How long to stay in Boston proper;
3) Where in Boston to stay;
4) Whether we should spend time around Cape Cod;
5) What to see north of Boston; and
5) Any other info/advice you can provide.

I already booked a hotel in Danvers for the wedding and in Boston as placeholders, but am open to your suggestions. We will likely travel Wednesday to Wednesday. We have two evening events (Thursday and Friday) in Manchester by the Sea prior to the Saturday wedding so on those days we will likely stay north of Boston. Any help will be greatly appreciated!

Boston - Freedom Trail is a must. Takes you by North End, which means Neptune Oyster and Mike's Pastry.

North of Boston -- Whale watch tour out of Gloucester (check out the "Perfect Storm" bar while there.
Salem -- everything witches
Keep going north to Newburyport, keep trucking up 1 to Portsmouth, NH and into Maine

Check out Nubble Lighthouse in York, hit up a nice lobster shack or 2 (favorite is Cape Pier Chowder House in Kennebunkport), then take the Lobster Cruise in Kennebunkport (will cruise you by Walker Point to see the Bush compound). On to Portland.

NE is so small and closely situated you can to all of the cruising around in a day.

Edit because forgot: Real NE boardwalk in Old Orchard Beach, Maine

We have family who live on the Cape so we have spent a good amount of time there. First week of June could still by slightly too cool to go swimming. Heck, August is hard to swim there too. If you can plan a weekday trip for 1-2 nights, then it would be worth it, but it sounds like you can avoid Friday/Sunday drive to/from the Cape, due to traffic.

You will absolutely love your time in Boston.

As Htown said, take the Freedom Trail. My only suggestion is that you start at Faneuil Hall Marketplace and grab lunch (lobster roll, NE Clam Chowder, etc.) then head out from there. Your walk will take you to the Old North Church as well as Paul Revere's house (which was already 100 years old when he purchased it). Yes it's touristy, but you'll enjoy it IMO.

Let me say this...you will have so many places you'll want to visit but not enough time. Just a few of my favorites...

Take the high speed ferry out of Hyannis and day trip to Nantucket. The Whaling museum is an absolute must.

Spend a day in Newport Rhode Island and check out the many mansions from the Gilded Age (the Breakers is the largest and my favorite).

The New England Aquarium (in the downtown area), though not one of the largest aquariums in the United States, is worth consideration.

Fenway Park.

Book the Amtrak out of the North Station and day trip or overnight in Portland, Maine. It's about a 2 1/2 hour train ride. As much as I love Boston, Portland is a gem. It's crazy how many Bostonians head to Portland on the weekend.

Cambridge (where Harvard and M.I.T.) are located, is a really neat area.

Whatever you opt to do, you will have a great time.

Bump this

Going to Boston to work on weekends in late Feb

I will have either 4-5 days or just 2 because of another potential side trip

any more suggestions then the ones above?

Best Clam Chowder ??

Weather will likely be cold so while I have no problem outdoors will do indoor things somewhat

Side trips to the west side of town possibly depending on the other side trip that is the way we would be headed

Some cool bars around Harvard if you want to hop around there and see the campus also if feeling like getting away from the Boston downtown area. Quick subway ride away

You'll have a great time. Just avoid going to Salem. It's an overrated tourist trap.