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Late winter road trip Deep South

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I'm hoping to get a slew of ideas to consider for my winter "get out of the cold" trip to the south. I know I'm starting early...one of my quirks... My preliminary planning for a part Feb/part March road trip from Ohio will probably be solo and for around 30 days. I'm trying to capture interests such as local foods, scenic drives, history, architecture, a taste of the blues, beach, strolling town. I wish to avoid interstates most of the time and am mostly interested in medium and small towns which offer something of interest... I also don't like 1 night stays - getting a break from driving is nice. I prefer my time behind a wheel maxed out a 6 hours (not including sightseeing stops) in a day.

My draft looks like this:

Cincinnati to Memphis (7 hrs - 1 day) Interstate to get rolling on this trip
Memphis 2 nights

Cleveland/Greenwood/or other town 2 nights - I'm planning to stop in Clarksdale on the way. I will set aside a day to visit towns/sites in the area. Ideas?

Galveston, Tx 7 nights - was there recently for 2 days and missed seeing/doing a lot
New Orleans 2 nights - visiting family, been there before

Dauphen Island, Orange Bay, Oyster Beach, or Pensacola, etc. 5 nights - looking for suggestions for a beach town that is reasonable in cost, pretty, relaxing, warm (60's+). Would stroll beach/boardwalks, shop, dine, take a boat ride, sightsee and take day trips. Any ideas for those day trips and sightseeing?

Natchez 7 nights - Seems lots to do & see (plantation tour, shopping, historical sites, Indian culture), day trip to Vicksburg and looking for ideas on other day trips.

Natchez Trace to Nashville - 1 or 2 overnights - I realize that this is a slow route. Suggestions for stops or must-sees nearby?

Nashville - 2 nights - visiting friends, been there before
Back to Cincinnati

I am hoping for answers to the above questions and any suggestions for dining, accommodations and things I haven't thought of. Finally, as a solo, I have a healthy sense of cautiousness (so if you wouldn't want your mom to go there by herself, please don't suggest I go).

Thank you to anyone who takes the time to respond!


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