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Thoughts on an itinerary?

New Orleans, LA
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Thoughts on an itinerary?

I'd appreciate your thoughts on my plans for an upcoming family trip to Boston -- 2 siblings and their families (kids are teens who like history), along with the grandparents. We vacation together for two reasons -- to visit, and to see the sights -- so we really like a leisurely sightseeing pace.

This year we've decided on Boston, and we're very excited. We'll be there in late July, staying in Brookline, and planning to take the T almost everywhere. Here are my thoughts for our week there (We're arriving Saturday afternoon and will probably sleep in on Sunday). I'm hoping that we'll have some "open" time to do some walking around downtown Boston.

Day 1 -- Sunday afternoon -- Constitution, Bunker Hill, surrounding area.

Day 2 -- Monday -- Freedom Walk (except for what we've seen on Sunday), lunch, North End and Downtown. Monday night -- Red Sox game.

Day 3 -- Tuesday -- Day Trip to Lexington/Concord (we're considering using a small private tour group for this, since we won't have a car). Perhaps a tour with a stop at Harvard Yard on the way back?

Day 4 -- Wednesday -- JFK library; afternoon visit to MIT? (nephew wants to see it).

Day 5 -- Thursday -- Salem

Day 5 -- Friday -- Museum of Science; Gardner.

Day 6 -- Saturday -- we'll decide on that once we get there! We'll kind of go our separate ways that day.

I'd appreciate any suggestions. Thanks in advance!

Level Contributor
5,909 posts
1. Re: Thoughts on an itinerary?

The JFK birth place is not too far outside Coolidge Corner in the Allston Direct.

Brookline to Harvard Square is a fast inexpensive way by cab.

Doing a tour bus to Lex/Concord is a good way to see the area.

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2. Re: Thoughts on an itinerary?

Day 1: Why not head over to Long Wharf where you can catch a inner harbor ferry to The Constitution. Bunker Hill and The Constitution are over in Charlestown and there's really not much else around that area for a tourist to explore. On the ferry back, you can walk over to Faneuil Hall Marketplace and check out the hustle and bustle there. The kids will enjoy the street performers there.

Day 2: Looks good. Consider stopping for pizza at Pizzeria Regina in the North End. Very good pizza!

Day 3: You could take this tour for Cambridge, Concord and Lexington, but to truly enjoy all there is to see, a rental car or private tour is your best bet.


Day:4 I see no reason why you couldn't swing over to MIT after the JFK. You will already be on the Red Line of the subway, so just take it to Kendall/MIT stop on your way back from JFK.

Day 5: Salem

Day 6: The kids will really enjoy the MOS. While I love the Gardner, the teens might find the mummies and other artifacts of the Museum of Fine Arts more to their liking. Whatever you decide, since both are fantastic Art Museums, with the MoFA much larger.

Day 7: Maybe explore the Back Bay? The Public Garden is worth a visit and maybe a trip up to the Prudential Skywalk to get a aerial view of the city and beyond.

Boston, MA
Destination Expert
for Boston
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3. Re: Thoughts on an itinerary?

Looks very doable and not frenetically paced. On Sunday, while you are in Charlestown you may consider a meal at the Historic Warren Tavern. It's right off of Main Street between the Navy Yard (where the USS Constitution is) and the Bunker Hill monument.


New Orleans, LA
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4. Re: Thoughts on an itinerary?

Thanks for the comments. I'll take the pizza and Warren Tavern suggestions -- I had looked into Warren Tavern as a possiblity on that first day. It's also good to know that MIT would work pretty easily after the JFK museum.

I think a private tour might be our best bet for Lexington/Concord, and I'll take a look at that.

Baltimore, Maryland
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for North Conway
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5. Re: Thoughts on an itinerary?

If you are going to Salem, include Rockport on that day. If is a wonderful little town with shops,arts/crafts food, ocean, history, etc.

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332 posts
6. Re: Thoughts on an itinerary?

If you can get to MIT by 3:00 pm, you can take a student-lead tour of the campus. They also have tours at 11:00 am but that's probably when you'll be at the JFK Library.

MIT Tours information:


You can also pick up a map with a self-guided tour on it at the Information Office.

7. Re: Thoughts on an itinerary?

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