Chesapeake Bay

Through Hot and Cold, Calm and Breeze

The Chesapeake Bay was one of St Barts Sailing’s regular long-weekend destinations for many years. For several trips we chartered from small towns on Maryland’s eastern shore. In 1998 and 1999 we ventured into the sailing Mecca of the northern Bay, Annapolis.

The Bay is very shallow–with depths outside the channels typically under 10 feet. Throughout the summer it languishes under hot, humid sun and very little wind, and spawns hoardes of jellyfish and sea nettles. Visiting sailors, who come in the spring and the fall, take pity on the locals who have to sail here all summer.

Starr surveys her boat prior to departure.

Understandably, Bay boats are shoal draft and heavily canvassed (their keels don’t go very deep, and they have big sails). Even so, running aground in the soft, muddy bottom is a rite of passage, and having to use the iron jenny (engine) to make passage is expected.

Every Bay charter trip includes at least one crab feast. The most notorious of these was the year that Dan and Mia were the experienced crab pickers, Mike and Betsy ordered other food, and Danielle, Jennifer, and Stewart got seriously drunk since they couldn’t eat enough crab to absorb the beer. To make up for it, Dan and Mia picked the leftover crabs the next day and Betsy made a hot crab puff appetizer. We finished off the meat in “eggs crab benedict” the next morning.

Mike and Stewart plan the day’s itinerary.

That trip we we suffered high winds and cold temperatures. Wearing all the clothes we had brought we beat through choppy weather to Dun Cove. Snug in the anchorage, crab puffs consumed, some of the group curled up in the main bunk to watch a tape on the VCR, the boat’s power inverter humming away. Some of us braved the chill to enjoy the stars instead.

Late in the evening we realized we’d not eaten the “Midnight Extasy” chocolate cake. Out it came, and with the first bite those of us who had been nearly asleep were suddenly wide awake. After bouncing off the cabin walls for a while, we started to wind down. Mike tried to open the door to his cabin, and it didn’t move. Stewart had gone to sleep on the floor and he was blocking the door. More specifically, his head was blocking it. Repeated banging of the door against his pillow brought no response. Shouting and pounding on the door was useless. Stewart had a reputation for being a sound sleeper, but this was amazing.

Finally Dan went on deck and climbed in to the cabin through the open hatch. Stewart insisted, upon being shaken awake, that he’d never heard a thing.


Dan and Betsy bundled up on the “Cold Chesapeake” trip.

In 1998 we chartered Pain Killer and Lady Jane in Annapolis. The smaller Lady Jane zipped along prettily. Party boat Pain Killer plodded through the light swells and lighter wind, struggling to keep her sailing mate in sight. Entering Dunn Cove (yet again), Pain Killer was leading, having given up on sailing while Lady Jane was still out playing. A lesson in reading the channel was quickly learned as Pain Killer ground to a halt. Mia had steered her too close to the edge of the channel, although not quite out of it, and she was hard aground.

“Damn!” She growled. “Everybody go up to the bow!”

The urgency in her tone mobilized the crew, who dutifully followed Stewart forward. But no amount of counter balancing could free the boat. Pain Killer slowly spun around as the outgong tide carried her in a pivot on her keel, the propeller churning up mud as Mia tried to power her off.

Finally Lady Jane came along, and Mia gladly climbed into the dinghy to carry them a tow line, letting Stewart handle the big boat’s helm. Later that evening, sungly rafted in the cove with hot-buttered rums all around, Pain Killer‘s less experienced crew members admitted that they thought, when ordered to go to the bow, that Mia was made and didn’t want them around, and the way Stewart had quickly complied they’d figured they better get out of her way.