The great thing about sailing in a new location for the first time is that you have no idea what to expect. Without a laundry list of hot-spots-we-always-visit, your itinerary is a blank canvas, ready to be painted and repainted as you see fit.
This was the case last April when a crew of comrades and I chartered a boat from Annapolis Bay Charters in Annapolis, Maryland, for a week of exploration on the Chesapeake Bay. We’d sailed together in college on Lake Michigan and chartered in various locales since, but we knew next to nothing about the Chesapeake. That meant we were game to go anywhere the wind took us.
The suggestions poured in. A coworker suggested Oxford; a racing friend from the log canoe Jay Dee insisted we visit his beloved St. Michaels; Scott at Annapolis Bay Charters encouraged a stop at Gibson Island; and our crew of BVI fanatics couldn’t resist a Painkiller at Pusser’s in Annapolis. Our canvas filled up quickly with an itinerary as colorful as the bay itself: part wilderness and part urban waterfront, with the two distinctly different Western and Eastern shores, a six-day, seven-night discovery of the Chesapeake.
The Big City
The Boston-based portion of our crew picked up the Fountaine-Pajot Belize 43 Cataway at the Annapolis Bay Charters base. We took her for a spin out on Back Creek and around the point, into Annapolis, giving ourselves time to get a feel for how she handled. The Chicago-based members of the crew were waiting in Annapolis, so we motored into the infamous Ego Alley, a long and narrow water-runway that juts into the heart of town. The Alley lived up to its name; we felt like real superstars, performing our sexy pirouette before nestling into a prime dock spot. In the summer, hoards of tourists may have applauded our boathandling, but this was the shoulder season, so our only ego stroking came in the form of high-fives.
Annapolis is a sailor’s town if ever there was one, and with the entire gang now in tow, we happily filled a day there. We strolled the pristine campus of the Naval Academy, window-shopped for nautical clothing and knick-knacks, observed a college regatta in the bay, and enjoyed dinner at the Ram’s Head followed by a Painkiller (or two) at Pusser’s. We could have spent days in that town, but there were other sights to see, so off we sailed.
The Only Boat at Anchor
Marylanders refer to the harsh winter of 2010 as “Snowpocalypse,” and it came as no surprise that our April charter started on a cold note. We bundled up to sail north, with temperatures in the 40s and a stiff breeze from the east. A pesky drizzle pursued us all morning, creating that perfect combination of cold and wet that only sailors seem to think is fun.
As we sailed beneath the Bay Bridge, the rain finally eased and we made our way toward Gibson Island and Sillery Bay, where we set our anchor in the lee of Dobbins Island. Though Dobbins is nearly surrounded by steep clay cliffs, a long dinghy dock on the windward side provided access to shore, where we discovered a nice walking trail. Following that bone-chilling sail, we were glad to stretch our legs and get a bit of exercise. That night, with no rain and only a hint of a breeze, Cataway rocked us to sleep, the only boat in the anchorage.