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Help planning a southeast and east coast road trip for April

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You all have been so helpful on my other thread with your advice on where to stay in Boston before our flight to Dublin and on to France that I thought I would ask for your insight and ideas on planning our driving trip up from Florida to Maine before we arrive in Boston on April 30th.

We will be renting a car in Florida when we arrive and will be dropping it off at Logan on our way into Boston (we won't keep the car in the city while we are there-just take a cab to Logan for our flight. We have already booked the car and are aware of the drop off charge-but I think we got a good rate).

Here is what we are thinking for the trip so far:

April 1: spend three nights in West Palm Beach (see friends there)
April 4: arrive and spend 3 nights in Tampa (see friends there)
April 5th: 1 night in Savannah
April 6th: 3 nights in Charleston
April 11th: 1 night in Atlanta
April 12th: 4 nights in Nashville
April 15th: 1 night in Asheville
April 16th: 1 night in Richmond (just need to break the drive to DC area-is this a good place?)
April 17th: 4 nights near Takoma Park MD (see friends there)
April 21st: 2 nights Saint Michaels, MD
April 23rd 2 nights Rehoboth Delaware
April 25th: 2 nights New Haven (just need to break the drive to Maine-is this a good place?)
April 27th: 3 nights Portland Maine
April 30th: drop car at Logan and spend 3 nights in the city
May 3rd: 9PM flight our of Logan to Dublin

We are pretty open on number of nights we spend in places and the route we take. I would love input from folks about our choices. We aren't after staying in the big cities on this trip (aside from Boston because I have never seen it) so that is why places like Philadelphia and NYC are missing. We love road trips and eating :) so any suggestions about where to stop, beautiful roads, local cuisine, etc. would all be welcome.

Some specific questions:

Is it too much to think about continuing on to Louisville-I keep reading nice things about it but it seems like it takes us really far West and makes out total mileage pretty high since we prefer driving 4-6 hours a day versus 8 hours straight.

We are to Maine really eat lobster. I know we will be there kind of early in the season (April 27th), so it seems like a good idea to stay in Portland itself versus other places since I assume all the small coastal towns may be pretty dead that time of year.

Everything is really flexible at this point-so feel free to give advice about all of it. Aside from one other driving trip from DC to NY that focused on the bigger cities, we are pretty much novices about the area-so all thoughts would be appreciated.

Thanks!

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