I had the fortune of living in Key West for 2 winter seasons. We would drive to KW in Sept, back to NYC in Dec, back to KW in Jan & back to NYC in May.
I-95 is incredibly boring for me until I see palm trees in South Carolina. As others suggested, dont stop for South of The Border- the billboards you will see for at least an hour prior to the entrance are far more fun then the actual place. Also, take I295, instead of 95S around Richmond. Same for Philly (I295.)
We travelled with dogs, so we stayed at Courtyard by Marriott along the way & also Red Roof Inn.
I loved hitting up Waffle House, as we dont have them in NYC & they are open 24/7. There are a bunch of quick service chains we dont have in NY that we tried out like Cracker Barrel & Bojangles. There is a cool website called Roadfood that speaks of excellent BBQ restaurants close to 95S whilst driving down (we've hit B's BBQ in Greenville, NC. Smithfields Chicken & BBQ- Lumberton, NC. Sweatmans BBQ in Hollyhill, SC.)
There is also a website that tracks fuel prices along 95S too.
Nicks Fish House in Maryland has all the Old Bay goodness on seafood with a large waterfront dining area & live music (at least they did 2 years ago; check the website.)
Pee Dee State Farmers Market in Florence, SC (right off 95) was very great for fruits, honey, local snacks & crafts.
Carolina Heritage Outfitters offers a canoe trip along the Edisto River to a treehouse that you can stay in overnight!
We also enjoyed a night in Savannah, GA & Charleston, SC. Extremely adored the retro Thunderbird Inn in Savannah.
We bought an electric kettle, cafetiere & thermos for great coffee in the hotel in the AM & early driving hours. A few non-perishable snacks from Trader Joes (nuts, trail mix, olives, sparkling water, crackers) but really enjoyed seeking out fun, local food on the road trips.
I obsessively tag locations in google maps to not forget. Enjoy!