NY to Florida Keys. How difficult will this trip be?

Head down the Dismal Swamp Canal route and stop in Elizabeth City ,NC. ! Onancock and Cape Charles ,VA on the Eastern Shore, also Oxford ,Md. Reedsville,and Urbanna VA

I made the round trip from FLL to Charleston & back last year. (54’,4.5 draft 19.5’ air draft ) Biggest skinny water challenge was between Jacksonville & Fernandina. NB leg I ran it near low tide and hit bottom / singed my port prop & shaft. SB ran the same leg st high tide and was no problem. My advice Run it high tide. Or go outside between Jacksonville & Savannah if weather permits.

I loved the SC, GA, North Florida parts of the ICW . Charleston, Beaufort SC, Hilton Head, St Simon, St Augustine & New Smyrna we’re all very cool . Worst part of trip is between Palm Beach & Miami. SB leg once you get to Southern Blvd (@Mar-a-lago) bridges & No Wake Zones will slow you down

Most appears to have been said but I would wait at least another month. Did Ft. Laud to NJ once in March and the days we hit cold and snow from Va. to NJ sucked.