You guys are the best!! Thanks for all the wonderful suggestions. I think I have a clearer picture now of how to organize our trip...just keep your fingers crossed that the weather cooperates and my feet don't give out :)

If you want/need to drop something I'd suggest the Aquarium unless you're really interested in fish!
It's something that's popular with children and it's a great indoor activity if the weather is iffy but in June I'd skip it.

I suggested not doing the Gardner and the MFA on the same day as it's too much of a good thing (too much art/indoors) but BOTH museums have great cafes and the Gardner has outdoor seating too so bear that in mind.

Is trying to do the duck your on your arrival day a good idea? If your plane is delayed, you might end up missing the tour.

I went to the MFA and Gardner in the same day and it worked out well for me.

I like yk's suggested itinerary. I second her recommendation that you spend at least some time in Harvard Square/Cambridge.

I would substitute a tour of historic Beacon Hill and the Boston African American National Historic site for the aquarium, but then I was an American studies major.
http://www.nps.gov/boaf/index.htm

I wouldn't consider the Aquarium a must see either. It's not one of the best, if you have time, great, but don't rush to fit it in. Walking the Freedom Trail and spending at least some time in the North End and Beacon Hill would be the musts for me. Taking a tour of Fenway and/or heading to the area before a game also ranks high on my list.

If you're coming to Gloucester, Wingaersheek is a really pretty beach. It isn't nearly as big as Crane, but very scenic. Also, I would say that Halibut Point State park in Rockport and/or the Coolidge reservation in Manchester/Magnolia are musts. I don't know if I would call it a must, but Hammond Castle in Gloucester has a really pretty setting. In the past, you could walk the grounds when they were open without going inside. Not sure if that's still true. It's interesting inside, but you might just want to see the outside setting on the water if your time is short. Note: Ipswich, where Crane Beach is, is about a half hour drive from Gloucester.

Halibut Point is nice, but I don't think it ranks as a must-see for a visitor from out of town. If you were going to be in the Rockport/Gloucester area for several days, maybe, but not if you have only one day on Cape Ann.

If we're only doing one day at Cape Ann, what's the best place(s)/beach to see? I've heard both Crane Beach and Singing Beach - is it just a matter of personal preference?

Crane's Beach will be the largest of these. Both Wingaersheek and Singing Beaches are nice, but smaller. I'd pick Cranes if I could only choose one, but they're all enjoyable to visit.

If you don't have a car, Singing Beach will be the easiest to see, as it's about a half mile walk from the Manchester stop on the Rockport commuter rail line going out of North Station. On weekends from mid-June to early September, there's a bus that runs from the Ipswich stop on the Newburyport commuter rail line to Crane's Beach. There's no public transportation near Wingaersheek that I know of.

If you are in Boston on Sat. June 26th, you can still enjoy the VERY best of Boston (it is seasonal and their last day of the season)..The Chocolate Bar at The Langham Hotel in Boston is AMAZING (if you love chocolate). It is basically a ballroom of chocolate..truly a sight to see. You must have reservations..(4 "seatings" during the afternoon). Not to be missed.

Also ~ wasnt sure if anyone mentioned Fanieul Hall? That would be a first on my list. Yes, skip the Aquarium..nice, but so much more to do.

You MUST walk and eat in the North End (little Italy)..most any restaurant will be fabulous. Don't forget Mike's Pastry's!! World famous!!

Yes, Cape Ann is nice but I would also (if you have time) head to Newburyport. It is also on the North Shore and I personally think it is one of the most charming towns in New England.

For hotels under $200 in Boston and within walking distance to most of the attractions, I would suggest The Harborside Inn, The Back Bay Hotel(although that may be just above $200)and my favorite is Hotel Marlowe just on the other side in Cambridge. You can purchase now and get a beautiful room for $200...you won't be disappointed!

You can always walk over to Charlestown and take a tour on The Constitution! Not to dissapoint.

It is a great city..nice and on the smaller side so you will be able to fit in most everything. Food is great. Also, a walk around Harvard Square is so pretty..especially during the time you will be here..

Have fun!!

Faneuil Hall/Quincy Market is on the Freedom Trail, so if the OP takes this, they can't miss this attraction.

Mike's Pastries in the North End is in fact one of three excellent Italian bakeries there. Consider a taste test at Mike's, Modern Pastries, and Maria's. They're all very good. The North End is also on the Freedom Trail.

My favorite place to stay is John Jeffries House --out the door is metro stop. (next 2 stops over the river is MIT, then Harvard,
Other direction goes downtown .Also out the door, you can walk down cobblestone street to cafe, tiny grocery and deli's and keep walking to Boston Common.
I don't usually choose B & Bs but this an exception-- has small breakfast and rooms are a little small,but very comfortable bathrooms spacious. I tried to check availability for your dates but you must do this by e-mail.
This is a "side issue" but it is across from Mass. Gen. Hospital in case you feel poorly !!!
.http://www.bedandbreakfast.com/massa...ies-house.html

My travel buddy's brother (who lived in Boston for 8 years) is recommending the Boston Park Plaza Hotel. Any thoughts on this place?

It's at a good location; but otherwise, it's quite worn down and rooms are tiny.

Just an FYI, Ipwich is not on Cape Ann. :)

If Cape Ann is still in your sights, I'd recommend you the artists colony in east Gloucester, Rocky Neck. While I really like Singing Beach, in season, there is no parking there unless you find a meter about a half mile away. Crane's beach is very nice, but check the horse fly season before you go. We once paid a pretty penny to park, but the flies were so bad, we left.

CBWest, Here is a link to give you information on Crane Beach. The green head flies will not have arrived when you will be there. They typically come around July 11th and last about 3 weeks. If you are a beach lover yu will be very glad you went.

http://www.thetrustees.org/places-to...the-crane.html

Halibut Point is special place. I love picnicing on the rocks overlooking the ocean(we discreetly pour our wine as it's not allowed) I've been going there for years before it became a state Park donated by a doctor.
copley T stop for the library and many of the hotels
and shopping on Newbury and Boylston Streets. Across from the library and in Front of Trinity Church, starting in May on Tuesday and Fridays, there will be the farmers' market.
There's a boat that goes to Provencetown in the morning. It leaves you there with enough time for lunch before the return trip.