There is no need to drive a rental car from NYC to Washington. Use either the train or bus. Paying for parking at a hotel can be expensive.

Most places with jazz wont allow an 8 year old - you need to go to one of the few places that have a performance - but not drinks - or a meal with jazz. As for a 4 year old - well obviously too young for almost all of these places. I would agree that your best bet is to try for a brunch with jazz. And do check before trying to bring such small kids into anyplace in the evening. (Typically kids under 5 are not allowed into most shows or performances - unless they are specifically aimed at children - certainly not NY theaters - never mind the cost of a ticket for a child who won;t really be interested.)

Go to New Orleans! It's a great city with history and great music and there are plenty of places that you can go with kids. Jackson Square- you can see musicians playing jazz in the street, a carriage ride through the city, the outside patio at the restaurant by Marguaritaville has jazz music in the afternoon, sometimes there is a musician or 2 outside of Cafe Du Monde, the aquarium is tremendous, take the streetcar down St Charles-stop at Audubon Park and take the free shuttle to the zoo, grab a Muffalotta sandwich at Central Grocery and eat it in the small park across the street, Preservation Hall for jazz (advance tickets are cheaper), Frenchman Street for jazz, Steamboat Natchez-take an afternoon jazz cruise, haunted history ghost tours, Audubon Insectarium. New Orleans isn't just Bourbon Street. Have a great trip!

Totally agree Janice, go for it Anna, you and your children will have a ball.

I have a bias. I think three weeks and 2,000 miles and kids in a car is not the most relaxing of ideas. Every place everyone has mentioned has tremendous charm and interest but please recall that summer on the East Coast can be hot, though I suppose not any hotter than Malaysia. I would recommend you consider, NYC and DC- there are some really cheap inter- city bus deals, fly to Orlando- rent your car there and drive up to NOLA while picking a spot or two on the Gulf Coast of Florida, Mississippi or Louisiana for your beach break. Very reasonable, very pleasant.

I am now about to leave for the US in 2 weeks. After 4 months of cracking my head on where to go and what to do I have finally got some idea. I have basically bought flights tickets and booked rooms etc for most of my journey . What I could use help for is this. I decided to fly to DC after all from NYC and I have 4 nights in DC. I check out from the DC hotel on 24 July. I need to be in Orlando on 27th July so I have 3 nights i.e 24th 25th and 26th which I have no idea what to do with. I thought of driving down to orlando but I dont want to do the williamsburg route. See My hubby and I love visiting wine country and i hear Virginia has some vineyards. Hubby would also like to check out some horse racing (I understand you can take kids to the races in the US- how civilised!)So can anyone give us some ideas on how we can do this in the three nights that I have between DC and Orlando. Am quite happy to stop at a few places on route. Love to hear feedback!Apart from the above three nights I have sorted the rest of my trip and am thrilled about it! Thanks for all the feedback

Three days from DC to Orlando is not a lot of time to visit a lot of places
I am also amused by the recommendation of DC and NYC as an alternative to the "hot" southeast coast!! I NEVER to go NYC in the summer!!
There is a wine region in NC along I77 and i85 that is a bit inland from your route to Orlando, but no moreso than the Virginia regions, I'd guess, and it would be further along your way.
Awkward amount of time and distance, I think.
Just head down the coast--stop in Charleston for a quick look. Buy wine at the restaurants!! LOL