I've trailered that run once. My ex-next door neighbor was raised in that area and convinced me once to go fishing there. It's a long drive, full of bridge tolls. The fishing was "ok" but nothing to write home about. I can only imagine what the run would be on the water. Still, the scenery is nice and as you say, there are many places to stop in the event of an emergency or tiredness. Have fun :)

Sounds like a great trip!

The longest distance we covered at one time was from Hilton Head to Charleston. It's 60+ miles straight line but we were in the ICW so I'm guessing it ended up more like 65-70. It would have been fun but we went one way in rain (pre cold front) and returned in about 40 degree weather. This was in October. I'd like to do it during the summer.

80 miles offshore, trolled at 7 knts for 4 hours and 75 miles back in....longest trip to date.
Regularly run 50 to 60 miles out to start tuna troll. Always carry 10 to 15 ga of fuel for safety.