Departed Yacht Haven Annapolis. Passed through mooring field. Raised main and rolled out jib. Sailed out to Greenbury Point. Say 5 feet on depth sounder at one point after having tacked to sail away from Greenbury Point in the direction of Back Creek. Sailed out past Tolly Point. Returned downwind toward a collection, perhaps 40+, Optis at the mouth of Lake Ogleton (?). Escorted the Opti's, which were being towed by RIB's, back towards Spa Creek till forced to veer away to clear Horn Point. Experimented with raising traveler to windward side of the vessel. Resulted in improved sail shape, less weather helm, and more speed. Confirm this observation on future outings. Several times, sailed from the mouth of Spa Crrek to the vicinity of the small boat basin at the US Navy Marine Engineering Laboratory. Started engine, lowered main, encountered some difficulties with jib roller reefing. The unit stopped turning with the jib rolled up about 30%, was able to unfurl and then roll up completely after several times seeming to get stuck. Perhaps I was applying too much "back pressure" holding the jub sheet trying to get a snug roll ? Headed back to dock. Turned into the slip a bit early and consequently had to manhandle the boat a bit into the slip. Tied up and bedded down the boat. Left Annapolis at 19:18.