The regatta will present a challenge to the young sailors as they compete on five-person keelboats instead of the speedier two-person dinghies they’re accustomed to. Some racers will have only one day to practice on the larger boats before the regatta. “Most of them don’t have a ton of experience with keelboats, so this is a really cool opportunity for them,” said Allsopp. “It’s like if you were to race in a truck versus racing a really twitchy sports car like a Ferrari.”

 

After three hours of racing, the winning team will be presented with a trophy designed by nautical instrument maker Weems & Plath. The team that takes home the hardware will also win bragging rights for the next year.

 

Four schools, Broadneck, South River, Archbishop Spalding and Key School, train together at the Severn Sailing Association in Eastport under the guidance of coaches Catherine Pelo and Caroline Patten. Attending three-hour practices three times a week as they prepare for the competition fosters a healthy rivalry among the teams as well as close bonds. “It’s a neat dynamic,” said Key School junior Christian Filter. “We’re really fortunate we get to practice with some of the best teams in the area. We kind of push each other and get each other every day to be the best we can be.” “It makes our area significantly more competitive than anywhere else in the United States,” said Broadneck junior Kate Selley. Annapolis has become a center of high school sailing talent. Every year, area schools send teams to championship races as far away as Texas, California and Canada. “Our district is very, very competitive,” Allsopp said. “Often, our local qualifiers can be just as difficult as [races] at the regional or national level.”

 

The regatta is one reason organizers expect the spring sailboat show to draw its largest crowds ever. Now in its fourth year, the event has already become the second-largest sailboat show in the United States. (The largest is the fall show in Annapolis.) “The spring show has grown dramatically over the years, and this is sort of the breakout year,” said Paul Jacobs, general manager of the Annapolis Boat Show. This year, organizers have shifted their focus toward providing attendees with a more interactive experience, taking the action off the docks and onto the water. In addition to the regatta, the three-day show will feature free boat rides and classes for first-time sailors. “I think that the future of boat shows is getting people out on the water – the experiential, interactive aspect of it. … That’s where the fun is,” Jacobs said. “It’s not just go to the show and look at boat shoes; we’re really trying to make it more interesting and fun. We have parties. We have a regatta. We have alcohol tasting and food tasting.”

 

Organizers hope the regatta, sponsored by J World sailing school in Annapolis, will become a tradition among local schools. “We have six teams competing this first year, and who knows beyond that?” Jacobs said. “The sky’s the limit.”