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Boston - itinerary and walking Freedom Trail vs. trolley tour

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We (me, husband, two college aged boys) will be stopping in Boston for two days before our annual Cape Cod vacation. I have no excuse as to why none of us have been to Boston up until now, but there's a first time for everything!

We only have two days, and the first day will be an approximate 7-8 hour road trip from Buffalo. Hoping to leave home around 5:00 a.m. We will check in to our hotel (or at least leave our luggage until check-in later on) and hit the road. Staying at the Marriott Long Wharf. Day 1 is for the boys - they want to hit the Sam Adams Brewery (I could seriously do without that, but what the hell?). Following that up will be a late lunch / early dinner at Doyles, as all the guys want to check out a neighborhood Irish pub.

I've checked out the "T" stops - seems easy enough to navigate. Boys would like to check out Newbury Street area afterward to check out a Nike store and the general neighborhood. Back to hotel to get into our room and rest. Maybe walk around a bit in the evening to Quincy Market area.

Day 2 is my pick - history day! I know there isn't enough time to see everything. I understand the Freedom Trail isn't all that long and very doable with the right shoes. And I would like to cover most if not all of it. But I'm also hankering to see Beacon Hill. If we take the hop on/off trolley tour, it does detour over that way. But I'm not sure if it covers all the historical sites on the Freedom Trail.

Can anyone offer any insight? Thanks.

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