American city with the most colonial heritage (live, largest, life)
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In this order: Philadelphia 1st, Boston 2nd, Charleston 3rd, and NYC 4th.
NYC: Everything has become urbanized. The only historic (colonial) sites left are sites like Trinity Church.
Charleston: This city has a lot of colonial architecture but most if it is remake. There is also a lot of tourism sites to see but the amount is not on level with Philly and Boston. Charleston is a great city for a colonial history buff because the sites range from British to french to spanish to african american influences. There are a lot of forts and plantations you can visit.
Boston: Boston is another level to Charleston. There are a lot of historic sites but a lot of them are gone due to the Big Dig and highways that tore through the city years back. But the Freedom trail is a very fun experience to take. You can see The Old North Church, Quincy Market, Paul Revere's house, Bunker Hill Monument, Beacon Hill. The freedom trail is what ranks Boston a notch above. This is a throw in but Salem and Plymouth, while not in the city but somewhat near (30 min-2 hours away) are also very historic sites.
Philadelphia is the alpha of colonial history. Independence Mall is the most historic square mile in the US. You have Independence Hall, Liberty Bell, Carpenter's Hall, old meetinghouses (quakers), Christ Church as well as others, Town Squares, Society Hill, Penn's Landing, Market Street, Old Pennsylvania Hospital, Betsy Ross house, etc. Philadelphia trumps all other cities in colonial history. 30 min outside of the city is Valley Forge National Park, Pennsbury Manor, New Castle, DE, Washington's crossing, etc. There is a lot to do in Philly for someone who is very interested in colonial history
Another city you could have added was Williamsburg/Jamestown. I used to go there as a kid, well I still am one, and I loved it so much. While most is not original, it still feels very historic. The cobblestone and sea shell streets to the brick and southern wood buildings, it feels like you have really taken a step back in time. Plus you have William and Mary across the street so maybe you can turn it into a college visit as well.
Go to Annapolis for a day. Arguably a more satisfying and "colonial" experience than any of the others you listed, and you can see plenty of choice spots in Northern Virginia nearby.
I'd think about the Colonial Parkway by the Hampton Roads area. Jamestown, Yorktown and Williamsburg connected by this Parkway. You could stay there for a bit then head to Charlottesville (2 1/2 hours away) to take in the mountains and Jefferson's Monticello.
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