Boston

Pros: History, lots to do, fun
Cons: may involve some walking

I have spent a lot of time in and around Boston doing disc jockey functions.
If you are looking for American history, this is a great place to start. "Old Ironsides", Freedom Trail, Bunker Hill, Quincy Market, Lexington, Concord, and...

Pros: Youthful, hip locals, good restaurants and shops, good sightseeing
Cons: Expensive, Logan airport, the Big Dig

I travel often here for business. Logan airport is separated from the rest of Boston by some tunnels. During rush hour it can take quite a while to get through these. If you are coming or going from Logan airport during these times, be sure to plan...

Pros: history, attractive brownstones, easy to walk across, great people, small city, Go Boston Card
Cons: Pricey dining

The best part about Boston is that you can walk across the city relatively easy. The city evokes so much from its residents. They are interesting, intelligent, love their home team the red sox, and most of the people get their inspiration from the patriotic, proud history that the city boats. Though I don't always condone tourist attractions, I do believe you do a great injustice to the city of Boston if you don't at least walk the freedom trail, visit Harvard (the first university in the US) and really investigate the plethora of culture the city provides its visitors.

I'm a budget traveler myself, so I bought myself a Go Boston Card http://www.gobostoncard.com It's one card for a low price and you get access to all the great Boston attractions for free thereafter. Great program. It also includes day trips to surrounding areas like Cape Cod or Salem. Not to be missed.

Pros: The diverse food, the swan boats, fenway park tour
Cons: the bars and restaurants close soo early.  too many hills.

Stayed in Boston for fourth of July.  the city was very congested around the esplanade due to the fireworks.  we saw the fireworks from Boston common, and we were a lot more comfortable i'm sure.  Cheers is a great place to eat. 
Blue man group was an awesome show. 
the esplanade after the 4th was over was romantic and a great place to watch a sunset. 
see the uss constitution and the casson young ship next to it.
get a drink at cheers, there are two of them in Boston.
take a tour of fenway park.
walk up and down beacon hill and feel the history of the city.
shop at fanuiel hall. 
marvel at the beautiful churches and the public library.