When you hear sailors speak of intense racing, endurance, heavy wind, and large waves, things like the Volvo Ocean Race come to mind, not something called the “Sippy Cup.”
Yet all those terms apply to the most recent running of this 7 year old, annually run race on the upper Chesapeake Bay.
Designed as a way for smaller cruising boats to get into the racing scene and experience competitive overnight sailing, in a fun, low pressure, group situation, and the Sippy Cup runs on the same night as the more famous and higher brow “Governors Cup” popular with the more established Annapolis sailing scene.
With 25 boats registered for the race this year, the Sippy Cup has come a long way since its first incarnation, which featured exactly two boats, both McGregor 25s if I recall correctly.
This year’s Sippy Cup winner, Jim Van Lenten, aboard the Pearson 35 named Yellow Bird, was one of those initial racers, along with sponsor Dobbs and Suzanne Fryberger of Walden Rigging.
This year’s race occurred during the “Blue Moon” on the night of July 31st, 2015.
The starting horns blasted at 7:05pm for the Sippy Cup Class, boats with a PHRF rating of 200 or above. The Big Gulp class, boats with PHRF ratings below 200, began 10 minutes later.
The racers headed down the bay in light westerly’s, right up until the sun set, and the full moon rose, when the winds shifted suddenly from the East/Southeast, apparently caused by a strong sea breeze on the coast. This wind held until about midnight, when it began shifting back to the South West, and filling in to upwards of 20kts.
Many boats in the fleet suffered at the hands of strong winds and large waves, between Pooles Island and Swan Point, where the wind was pushing against an ebb tide, and the bay shallows up. Three boats had to retire during this phase of the race, one due to a shredded Jib Sail, caused by a furler failure. Two others ended up having to start motors to avoid a sticky situation near the shallows.
In the end, the first boats across the line came in just before sunrise at around 5am, finishing the course in just over 10 hours. Throughout the morning, the rest of the fleet crossed the line and arrived at D Dock at Port Annapolis Marina for some well deserved showers and naps.
Later that evening, an awards ceremony was held in one of the common area’s onshore, whereby ribbons were handed out, and the “Not quite so coveted” Sippy Cup and Big Gulp awards were loaned to the winning captains, reminded to give the trophies back before next years edition.
The next day was a long 10 hour motor in light headwinds back up to the North East River, with a few racers taking an extra night on the water by stopping at Rock Hall for the evening.