Doin' the Dismal...

Will asked me about the two options heading south - the Virginia Cut and the Dismal Swamp. Great question. 

Friends doin' the Dismal

I prefer the Dismal Swamp - it's wonderfully scenic, as you can see. Good protection from wind, and the stop at Deep Creek Lock to visit Rob, the lockmaster, is always a treat. Leaving the Dismal, you stop by Elizabeth City for a free night's dockage and the cruisers' welcome party each evening for a drink, and a rose for the ladies, a tradition started by two locals and now kept up by the city's Chamber of Commerce. 
The only drawback is that the Dismal takes longer to run, and isn't really feasible for boats drawing over six feet.
The Virginia Cut brings you to Virginia City and the Great Bridge Lock, a marvel to see in and of itself, plus lots of fascinating tugboat and commercial traffic. 
I usually do one route on the trip down, and the other on the return, just to enjoy the best of both worlds. The one other proviso is if the exit from the route will permit me to sail on the Albermarle. There is enough distance between them to make a difference in how you trim your sails.