As of 5/28, I am anchored at St Michaels, ten miles or so east of Annapolis.
Monty and I left the anchorage behind Cape Lookout and headed up the coast, starting out by beating south into the wind. The constant jolting of the striking waves made Monty completely empty his stomach, but by noon we had rounded Cape Lookout and were gliding along pleasantly, well on our way to Cape Hatteras (a most dangerous shoal in the days before GPS, lighthouses, and marker buoys). Before dark a pod of around fifteen dolphins joined us, frolicking around the bow. I brought Monty out and hold him while he noticed the dolphins with increasing interest and attention. One dolphin often tail-slapped the water, causing Monty to flinch, and the puffing of their breath also drew his glance.
On that first night, Monty felt practically soggy, his soft salty fur absorbing moisture from the steamy air above the Gulf Stream. I finally had to give him a rinse bath in the sink and he felt FAR more comfortable and pranced around the cockpit happily.... but still no interest in eating or drinking.
I decided to ride the Gulf Steam for another ten or fifteen miles past Cape Hatteras to get a nicer angle for sailing down wind, and at around 3am we jibed-over, turning our course north. Then, safely clear of shipping and shoals, wind and waves comfortable, we snuggled up in the cockpit and fell asleep.
The next day Monty recovered his appetite and the day and night went by uneventfully, other than a lot of traffic as I neared the Chesapeake around sunrise, so I ended up with a sleepless night, other than catnaps. I finally found a slightly sheltered spot a half mile from marshy-sandy shores and islets, dropped anchor, rowed Monty to a tiny island for exercise, then rowed back and loaded the dinghy aboard. I'll let a slightly younger me tell the rest:
"Here I am, sitting on the deck of the boat at 2:00 a.m, my dog and coffee by my side, sailing across the Chesapeake Bay (well, a "little" side bay called Mobjack Bay) in anticipation of changing wind. The six-knot, warm & humid, wind blows us north at around three kts over nearly flat water while the crescent moon shines low in the east among glowing wisps of cloud: absolutely delightful. Perhaps not as many stars as we would get in the open ocean, but very very pleasant.