I voted clockwise, but I think the final decision should be based on the weather winder for the selected time frame. If the off shore conditions are going to be better later in the designated week it might be better to run the Chesapeake first and take he outside with more favorable conditions.
It would be a good idea to set up a sailplan for both directions.
Voted CCW. I'm begining to be convinced we have better odds for favorable winds going that way at the end of May. Looking at the historical data for the last week of May, it seems the winds are s-sw at least 50% of the time.
Excerpt for the DE-MA-VA coast from Coast Pilot 3 below.
Spring brings milder conditions. Gales and wind speeds of 28 knots or more occur about one-half as frequently as they did in winter(winter figures were 5% gales, 10% >28 Kts) . Directions are variable, but south and southwest winds are most frequent by April. Waves of 10 feet (3 m) or more become increasingly less frequent; by May they are encountered less than 3 percent of the time. However, warm air blowing over still cold water brings fog. Visibilities of less than 0.5 mile (0.8 km) occur about 3 percent of the time; about one-half that fo visibilities less than 2 miles (3.2 km). Precipitation occurs about 6 percent of the time.
Summer, except for the threat of thunderstorms and a rare tropical cyclone, brings good sailing weather. Winds are out of the south and southwest about one-half of the time; westerlies and north-easterlies are also common. Strong winds are unlikely outside of thunderstorms, tropical cyclones, and an occasional frontal passage. Poor visibilities are also uncommon and waves of 10 feet (3 m) or more occur 1 to 2 percent of the time. Precipitation is encountered about 4 percent of the time and about one-half of the time is in the form of thunderstorms. Thunderstorms are most likely from May through September and often occur during the late night and early morning hours at sea. In squall lines winds can reach hurricane force in gusts.