The longest I managed single handing was a passage from Isla Mujeres to Key West, around 380nm covered in 48 hours. The second night was really tough with traffic and a wind over current situation that had the bow coming out of the back side of the swell into fresh air then crashing down. Up until that point I managed some cat napping, 15-20 minutes at a time, aided by a radar warning zone I set up. I also had an AIS transponder which helped with the heavy stuff.
Total respect for these guys though.
