I once had serious thoughts about hiring a delivery captain to take my boat to Marathon from Perryville, Maryland. I checked out three and the price was about the same - $3,500. They figured on two weeks because there would be a crew of two of three guys, so the boat would be in motion 24/7, weather dependent.
I opted to make the trip single handed, left home October 1st, damned near froze to death that year, caught up with Hurricane Sandy while in Myrtle Beach and ended up playing a 5 day Hurricane Party, which was neat. I was in Osprey Marina and while the wind at the tops of the trees was woofing at 60 plus MPH, down in the hole where the marina is situated, you couldn't find enough wind to fly a kite. The tide rose about 3 feet, than when things settled down, I resumed my trip south. It took me two months because of weather and breakdowns.
Despite the fact that I'm a really old fart and my health is shot to Hell, I would do this again in a heartbeat, and if even remotely possible, I'll be leaving Perryville on October 1st. I'm too damned old to tolerate winter in Maryland, anymore!
The trip down the ditch is a piece of cake, even single handed. I kept a urinal in the cockpit for those times when nature yelled at me, but I was unable, for safety reasons, to go below and use the head. Had a bucket with a toilet seat on it for the same reason - when ya gotta go - ya gotta go, especially when you're an old fart.
The big difference this time is I would motor/sail down the ditch to Morehead City, then if the weather permitted, head offshore about 10 miles and continue south, taking advantage of the Gulf Stream's back eddy currents that flow from north to south in the inshore waters. Then, I would get back into the ditch at Fernandina Beach, which is an easy-peasy inlet, and continue south to Stuart.