Racing Programs at the Annapolis Spring Sailboat Show

Date: April 15, 2025

Race to Annapolis - Sailboat Header image

Discover the thrill of competitive sailing at the 2025 Annapolis Spring Sailboat Show (April 25-27)! Whether you’re a seasoned racer or curious about getting started, this year’s lineup of racing programs offers something for everyone. From expert talks to hands-on sessions, it’s your chance to dive into the racing scene and connect with fellow sailors. Keep reading to find out what’s new for racers at this year’s show.

Friday, April 25th

The Everglades Challenge

Seminar Tent | 3-4pm

Get a firsthand look at the Everglades Challenge through the eyes of 11-time participant Jahn Tihansky. Join Jahn as he brings his journey to life with videos, photos, and personal stories in a presentation that’s both entertaining and inspiring. He’ll share how he and his teammate, Jeff Linton, prepared, navigated, and pushed through countless obstacles to not only conquer the grueling 300-mile course in their beach-launch boat—but also claim overall victory three times.

Racing Discussion with Pete Boland of the Sailfaster Podcast

Seminar Tent | 4-5pm

Join Pete Boland, Ian Morrison, Kristen Berry, and Sara Morgan Watters for a dynamic panel discussion on how beginners can break into sailboat racing with confidence – live from the 2025 Annapolis Spring Sailboat Show. If you’ve ever been intimidated by sailboat racing, don’t miss this insider look at the fastest ways to get on the water! Join the fun at the show or tune in via our livestream.

Saturday, April 26th

Oakcliff Collaboration Tour – Session One

Seminar Tent (pre-registration required) | 4-6pm

These high energy, collaborative sessions will empower sailors (and those who support sailors) to map their sailing future. Facilitated by the dynamic Dawn Riley, executive director of the world-class sailing organization, Oakcliff Sailing, each session will be customized for Chesapeake-based sailors and offer best practices and creative ideas, harnessing the collective knowledge of those in the room and the insights gleaned by Riley while conducting such workshops around the country.

The Saturday afternoon session will cover topics for sailors, such as mapping your success, what boat is best for your size body, physical fitness and nutrition, where and how to find sponsors or scholarships, the importance of pre-briefing and debriefing, networking in sailing, launching an Olympic campaign, joining a sailing rally, and more.

Learn more & register.

Sunday, April 27th

Oakcliff Collaboration Tour – Session Two

Seminar Tent (pre-registration required) | 9-11am

Sunday morning’s session will cover topics for those who support sailors, such as fundraising, club leadership skills, the importance of social chairs and social events, how to be a great race official, organizing a foundation for your club, how to build match racing and team racing programs, emergency protocols, working effectively with nearby sailing programs, and more.

Learn more & register.

How to Become a Great Crew Member on a Race Boat

Seminar Tent | 1-1:45pm

Ever watch the sailboats crossing the finish line near the Eastport Bridge and think, “I wish I were out there—but I don’t even know where to start?” Join lifelong racer and Annapolis Sailing School Director Ian Morrison as he breaks down the basics of a typical sailboat race. Then, dive into what makes a great crew member—from reading the water and positioning your weight, to why a positive attitude can make all the difference.

Updated Racing Rules Q&A Session

Seminar Tent | 2-3:45pm

The Racing Rules of Sailing have been updated for 2025–2028 – come learn what’s new from Bill Simon. A lifelong sailor and racer, Bill spent ten years as Race Program Director at Oakcliff Sailing, where he was deeply involved in high-level racing and official training. Now based in Annapolis, he continued to serve on Oakcliff’s board for five years after retiring.

Bill is an International Judge, National Umpire, and former Chair of US Sailing’s Judges Training and Testing Subcommittee. He currently serves as Chief Judge for Eastport Yacht Club and is a member of the CBYRA Area Appeals Committee.

SpinSheet Crew Party

Eastport Yacht Club (registration required) | 4-6pm

After your day at the show, head over to the SpinSheet Crew Party. Whether you’re brand new to sailing or a lifelong boater, SpinSheet’s Crew Parties are the perfect place to connect with fellow Chesapeake Bay sailors and get out on the water more often. Open to anyone looking for a boat to sail on—or a crew to sail with. Free and open to the public!

Learn more.

Best in Class Boats

This year’s show will feature a wide range of capable racing dinghies. Check out the Melges 15, Birdyfish, Viper 640, Flying Scot, and Lightning. If you find something you like, you can have it on the water for the next weekend. See full boat list.

Tickets On Sale

Purchase Tickets