For this trip I parked on the road, crossed over the riprap and lanched directly from the beach. If you were to head straight out, across the broad water, you would eventually end up in the Chesapeake Bay. I headed left (southwest) paralleling the beach, which soon gives way to marsh after you pass another riprap seawall that juts into the water. I soon crossed the wide mouth of Guilford Creek, which is relatively free of boat traffic except for the occasional crabber or fisherman. Depending on the tides, this is probably the only part of the trip where one might encounter strong currents and swells.
Crossing the Creek took me about 15-20 minutes of steady paddling. Nearing Jobes Island the water shallows and you can see any number of places along the beach inviting you to land and explore. Most of the island is marsh and low woods. According to what I could find out, no one has ever called this place home, but there was once a hunting lodge on the island. After being in the same family for generations, it was generously donated to the Nature Conservancy in 2002. I do not know what regulations, if any, are in place for this island, but I didn't think walking along the shore would be too intrusive. I would avoid the woods though, as it is home to one of the Eastern Shore's more notorious summer residents, the green headed horsefly. I followed the shoreline in a northwesterly direction eventually making it to where the island and the Chesapeake meet. I basically followed the same way back, stopping frequently, and all told it was about a 4 mile trip. Except for the birds in the air and the fish in the sea, I had this place all to myself, and it has become one of my more memorable paddles.
View Jobes Island 7.27.12 in a larger map