The Freedom Trail will take you into the North End, so you can plan your North End dining (Regina's, or somewhere else) around that.

The Duck Tours are very pricey. I had relatives visiting last summer and planned to take them . . . but the cost was way too prohibitive. We road the Swan Boats in the Public Garden instead, but your boys may not want to do something that innocent and childlike.

We live on the North Shore, and when teens my kids always enjoyed Gloucester. If you drive up, you can visit Hammond Castle on the way--you could get off the highway at, say, Beverly and hug the coast all the way north. Watch the DVD of Perfect Storm before your trip, and they'll enjoy seeing some of the sights in Gloucester. If you decide to take a whale watch, you can do so out of Gloucester.

If you decide to visit Salem, beware of cheesy "museums," and visit the Peabody Essex, pem.org, which has an entire Chinese house reconstructed inside. It's pretty amazing.

Harvard Square is a must: a good choice. Our kids--now college age--still love going there. There's great Indian food there, if they're adventurous eaters. If not, you all might like Fire + Ice restaurant, http://www.fire-ice.com. Years ago, this forum suggested eating there for a teen birthday, and it was a bit hit.

IF YOUr at the Colonnade...your practicall yacross from theDuck Tour.. that is a must..bur make reservations NOW..We are recentlly received a McCormick and Smith gift certificate .. in Park Square nd contrry to chowhound people..it was very, very good.. We like Skipjacks i8n Copley Square and Legal with so many retstaurants and the chowder being made in their commissary Im wary..If your going to go to a museum.. make it the Garrdner.. orif your going to Salem.. the Peabody Museum is an absolute jewel. Mikes Pastry.. its well worth the walk in the Noth End.

I meant the duck OR tram tour.Of course it's the tram (or trolley) tour that is hop-on hop-off.Sorry for any confusion.We were just glad to go on this on the first day to get our bearings, as all places of interest do not seem to be within walking distance. i.e. Harvard especially if you have limited time.

I meant the duck OR tram tour.Of course it's the tram (or trolley) tour that is hop-on hop-off.Sorry for any confusion.We were just glad to go on this on the first day to get our bearings, as all places of interest do not seem to be within walking distance. i.e. Harvard, especially if you have limited time.

Many of the Boston things to see are within walking distance (1/2 - 1 mile). The reason Harvard Square is not is that it is not in Boston, it is in Cambridge.

If heading north out of Boston to the Rockport area, you might want to stop off in Revere at Kelly's which is a local spot for great roast beef sandwiches, lobster rolls, fried clams, onion rings...etc. It's an outdoor stand and you can park across the street, and eat overlooking the ocean. The teens will love it there.

Also if looking for a beach that's close, Revere beach is ok, won't be as crowded as some of the others mentioned and is the closest to Boston.

The kids may enjoy watching the John Adams 7 part series on Showtime before heading to Boston and try to find some of the buildings mentioned.

Rather than a drive out of Boston for the day, consider taking the fast ferry to Provicetown as a day trip. The teens will love P-town for it's eclectic mix of a fishing village, Portugese culture, great food, mixed shopping and during that week a n atmosphere of a 24/7 party. You may see some whales along the way as well.

There have been some great recs for Boston here. I also love to visit the state house and just walk around for a bit.

And on the Freedom Trail I enjoy climbing the Bunker Hill Monument.

As for beaches, I really like Seabrook Beach in NH...just south of Hampton. It's more of a family beach. But I'm not sure there is any public parking around.

Seabrook also has a clam shack called Ceal's. I LOVE their lobster roll and fries. And Markey's is great for lobster and steamers.

If you aren't from a big city with a good selection of Chinese restaurants you might enjoy going to Chintatown for dinner or dim sum

If you were going to do a day trip, would it be to Martha's Vineyard, the north shore or P-town via the ferry? Can't decide. On the one hand, want to drive north to hit New Hampshire and southern Maine (someone posted about doing it just to say the kids have been in a new state, and that's kind of the idea behind it) so maybe that's not the best idea. I love the idea of Martha's Vineyard, but am afraid it might be too much in one day. So maybe Provincetown is the best option. Is the best whale watching out of Provincetown? Any thoughts?

I would definitely not attempt Martha's Vineyard as a day trip from Boston.

Provincetown by ferry is certainly possible. It will be very crowded. There are whale watching trips there and on the north shore

My husband's family would say go for the north shore/NH/southern Maine trip in order to count the extra states. I am not such a fan of visiting different states but I do love the north shore area for the seafood, beaches, historic towns.

Let me just add to the chorus...Martha's Vineyard is a very tough day trip. Its long, its a little hard to get around once there (relying on buses and the like) and its really just not worth it.

I think Ptown would be very relaxing and fun.

Just to make sure things are clear, when Boston residents, (well Massachusetts residents) say "north shore" around here, we mean the coastal area north of Boston, within Massachusetts, and NOT Maine or New Hampshire. I think the area around southern Maine and Portsmouth NH is really nice, and pretty, but again, kind of a lot for a day trip. I think if you wanted to make a day trip to the coast somewhere, and walk around cute villages and see the ocean, I would choose Salem and Rockport, which you can drive to fairly easily or even take the commuter rail, and would be a nice way to spend the day.

MV is a long day trip and will not do the island justice - you need at least an overnight.

A trip to Provincetown a much better idea - if you can fit in Arts Dune Tours - the boys would love that -

Other options: the fast ferry to Salem - that will get you on the water, and to Salem -

or stick to the Boston Harbor Isl cruises - go out to Spectacle Island or George's, or several -

What are the boys interests?
Harvard Museum of Natural History might interest them more than MFA - depending on their interests -

With teen boys I would definitely do the duck tour as an overview, early on - nix the trolley tours b/c they can likely walk everywhere and would enjoy more -

Definitely visit the tourist bureau on the corner of Boston Common (tremont st side) and go inside - great brochures and helpful assistance on ideas for all the things you mention wanting to do and everything mentioned here -

Thanks again for all the great advice--so many good ideas! I'm in the process of putting together an itinerary. (Half the fun is always in the planning!)Anyway, if we do MV, it will be as an overnight stay on Sunday. If not/regardless, we will head to Boston on Monday. I did change the reservations from the Colonnade to the Sheraton--got an even better rate. Bad idea, or comparable hotels?

Anyone want to help me weave together the itinerary for each day in Boston? We will be there for five days, leaving on Saturday, July 5. What I'm trying to do is make a tentative plan for which places make sense to see on the same day. For example, I think it's probably a good idea to do the JFK Museum and then check out Harvard Square and eat at Mr. Bartley's on one day. But how should I group the rest of the things we want to do in Boston: Duck Tour, Freedom Trail (about a half day and then the kids will be sick of it) Fenway Tour, Boston Common, Swan Boats, North End. Which make sense to do together on the same day?

Our kids are both boys, ages 13 and 16. Both love sports, one is a history buff.

For a day trip, if we don't do MV, we will go to Provincetown by fast ferry. If not, we will drive up the coast (at least stopping at Woodman's) and maybe even go into southern Maine if it seems like a good idea at the time.

I'd suggest doing the Duck Tour on Day 1, given that'll give you a better idea of where's where and layout of the city.

You can do Freedom Trail + North End on the same day, as it sounds like you won't be able to finish the trail.

Boston Common (+ State House? not sure if it's open to public) and Swan boats should be on the same day as they're next to one another. You probably will have time for the Fenway tour on the same day.

On Tursday and Friday (July 3 and 4), downtown will be mobbed, because of the special concerts on the Esplanade. Another reason to take your Duck tour early in the week!

Boston is a walking city; if you haven't already gotten a good street map, do it now and mark the places you want to see.

Your boys are 13 and 16 so all they are going to want to do is walk by the swan boats. That will take about 5 minutes maximum, if that - the swan boats are a classic Boston memory - but they are slow paddle boats and good for little kids, teens are certainly not going to want to wait in line to ride on one around a body of water they can walk around - so you will see them as you stroll through the Garden - cut up to the corner if you want so you can walk by the Make Way for Ducklings statue - and cross the street into Boston Common -
walk down to the far corner near Tremont and go to that large tourist information center -

As far as your other itinerary ideas:

If you think you are staying overnight on MV around July 4 , you best make your reservations asap -

otherwise, go with the day trip to Provincetown -

Also, if you do an overnight on MV - you will either need to rent a jeep for the two days or use the bus system - which is good, but just letting you know -
or do it by moped or bicycles - you would need to do some thinking on how much of the island you want to see and how you are going to do that.

As far as other things:

I think it's probably a good idea to do the JFK Museum and then check out Harvard Square and eat at Mr. Bartley's on one day.

*Personally, I wouldn't do JFK and Harvard Square in the same day - they are in opposite directions -
I would take the T to JFK Museum right after breakfast and when you are finished, see what kind of time you have left and choose something for the afternoon -

I would rather see you also do Harvard Square one day in the afternoon and work it into the evening -

I don't think the kids will be sick of the Freedom Trail if you do it right - get the info at that tourist center or print it from their web page online -

I have found the most successful way with our visitors is to walk the trail on our 'own time' - where we can spend as little or as much time on each part as we want - and along the way we interrupt it with other things - lunch, ice cream, shopping, a break in Faneuil Hall area with some street performers, seeing other things along the way - that way it isn't a 'boring historical walk' for the teens -

Also, think of splitting it up - and doing half the trail one day and half another.

I wouldn't go out of my way to eat at Woodman's their clams aren't that special. Just up the road is a nice restaurant called Periwinkles overlooking the water in Essex. Better and cheaper than Woodmans.

"Personally, I wouldn't do JFK and Harvard Square in the same day - they are in opposite directions -
I would take the T to JFK Museum right after breakfast and when you are finished, see what kind of time you have left and choose something for the afternoon -
I would rather see you also do Harvard Square one day in the afternoon and work it into the evening - "

But that's exactly why it makes sense to do the JFK Library and Harvard Square on the same day! Go to the JFK in the morning, then get back on the Red Line and take it straight to Harvard Square for the afternoon (and possibly evening as well). Frankly the JFK Library isn't in the same direction as anything else you're likely to do.

But I do agree that the boys are likely to just want a quick look at the Swan Boats, rather than an actual ride on them. Start in the Back Bay (at your hotel or the Arlington T stop), walk through the Public Garden and Common, go to the info booth at the far corner of the Common on Tremont near Park Street, then either start the Freedom Trail or take the Red Line from Park Street to the stop for the JFK Library.

Can't vouch for Woodman's; the last time I was there, the Nixon resignation was on the TV.

For your itinerary in Boston: part of of the Freedom trail is in the North End (Paul Revere's House, Old North Church, Copp's Hill Burying Ground) so you don't have to plan a separate time to go there

As noted in another post you could do parts of the trail at different times which might make sense if you want to stop at many of the 16 "official sites" along the way

http://www.thefreedomtrail.org/visitor/visitor.html

Although it is true that JFK library and Harvard Square are in opposite directions, both are on the red line of the T so it would be easy to go from one to the other once you are on the T. It would just mean passing back through Boston en route