The trip went great!! missed my tide window a little bit but did ok. Only issues I found where sliding on the tramp with the sleeping bags because the boat was at a small angle. Oh and it would be nice if someone had a better way to make the sail into a tent. I had problems attaching it down and then at best it was short (height wise) tent. I wound up using the JIB as a big wall to give us a little bit of privacy from the other campers (see photos). The tramp was comfortable but my little blowup pillow wasn't. Also in the future I might want to get the boat further up as the small surf noise right underneath when the time came in sucked.
I also mapped the trip out at this link.
Josh and I took the Hobie Cat out to Brickhill Bluff on Cumberland the most remote campsite they have (10.5 miles from the ferry landing so most tourists never make it that far). We left Friday about 11am but didn't arrive until nearly 3:50pm due to no wind for a little while and then tacking upwind for the last third of the journey. I managed to find most of the shoals and sandbars while doing my tacking, and had some fun watching some dolphins run near us.
The campsite was secluded and dark with an old fashioned hand pump for the well. We had wild horses wanderer through a few times, including massive amounts of sand nats. We slept on the tramp and used a sail as the tent.
Coming back the trip took us an hour and a half (steady north wind) and I only had to tack and jibe once. The trip each way was almost 14 miles not including the outbound tacking. Coming back we used the Brickhill river instead of going the ICW and passed some beautiful homes and the Plum Orchard Mansion.