By American Sailing
Table of contents
Setting Sail in Annapolis
There’s nothing quite like the Annapolis Sailboat Show. It’s part reunion, part discovery, and all inspiration for anyone who loves life under sail. The docks were packed, the energy was contagious, and the weather couldn’t have been better. From classic schooners to cutting-edge catamarans, there was something for every sailor—and plenty of chances to connect, learn, and celebrate the boating lifestyle together.
Aboard the Schooner Woodwind
We kicked things off Thursday morning determined to get out on the water—and luck was on our side. The Woodwind Schooner, a family-owned and operated business founded by former schoolteachers Captain Ken and Ellen Kaye, was offering rides to boat show attendees.
After 25 years of teaching, the Kayes followed their dream of introducing people to sailing. They had the original Woodwind custom designed and built, later adding an identical sister ship, Woodwind II, to their fleet. Their daughter, Captain Jennifer Kaye, now carries on the tradition with an extended “family” of friendly, passionate crew members who make every sail a special experience.
We sailed out into the beautiful Chesapeake Bay, circled a massive coal ship, and learned a few fun facts along the way (did you know the Bay averages only 21 feet deep?). With sunshine, a steady breeze, and 8 knots on the speedo, it was a perfect start to the weekend.
Learn more about the Schooner Woodwind:
Connecting with Our Schools
The American Sailing team spent the day exploring the show and visiting as many of our affiliate school booths as possible. We caught up with Belize Sailing Vacations, Blue Water Sailing School, Annapolis Sailing School, Horizon Sailing School in the Grenadines, Intelligent Sailing in Florida, and White Caps Sailing School, which just opened a new base in Greece.
It was inspiring to see our affiliates in action—meeting alumni, chatting with new sailors, and sharing their passion for the sport. Seeing how far and wide the American Sailing network stretches around the globe was a proud moment for our team.
Friday: Leadership, Learning, and Legacy
Friday started bright and early with the Sail America Industry Breakfast, where our CEO joined fellow leaders to discuss the state of the sailing industry and where it’s headed next.
A highlight of the event was the presentation of the 2025 Annapolis Boat Shows Distinguished Service Award to Paul “Bo” Bollinger, President and CEO of CRAB (Chesapeake Region Accessible Boating). The award honors individuals who have advanced sailing through selfless service. Bo’s leadership in creating the $6 million CRAB Annapolis Adaptive Boating Center and Marina has made sailing more accessible to all—a well-deserved recognition for an inspiring figure in our community.
Wind vs. WiFi: Can You Learn to Sail Online?
After breakfast, we made our way to the Historic Inns of Annapolis, where our Wind vs. WiFi panel took place inside the beautifully restored Governor Calvert House—a landmark steeped in Maryland history.
Located directly across from the Maryland State House, the property was once owned by colonial governors Charles Calvert and Benedict Calvert. Rebuilt in 1765 in the Georgian style, it has served as everything from barracks to a printing office and even features a preserved brick hypocaust—an early heating system once used to warm Governor Calvert’s orangery. Today, it stands as one of Annapolis’s most elegant hotels, still hosting state legislators during their sessions.
What is Wind vs. WiFi?
Can a YouTube video really teach you to tack? Can TikTok prepare you for heavy weather? Or is there no substitute for hands on the tiller and wind in your face?
Moderated by Senior Master Instructor Duncan Hood, the conversation explored how online learning and social media are shaping the way new sailors learn—and where real-world experience still reigns supreme.
Our panelists included:
- Mike Murphy, Great Lakes Sailing School
- Andy Cobun, Annapolis Sailing School
- Chris Rundlett and Chrystal Young, LTD Sailing – Living the Dream!
- Nichole Ortiz, Affiliate School Manager, American Sailing
Together, they discussed the balance between digital learning and on-the-water training, sharing stories that underscored the irreplaceable value of experience. The room was engaged, the energy was high, and Duncan’s signature humor made it both educational and entertaining.
Key Takeaways:
- Online courses are powerful supplements—but not replacements—for hands-on learning.
- Real-world experience builds confidence and intuition no video can match.
- American Sailing remains the global leader in experiential training, with over 400 schools worldwide.
Introducing SeaRM: The Future of Sailing School Management
Following the panel, we hosted a live demo of our new SeaRM platform, designed specifically for sailing schools. Presented by Jonathan Payne, CEO, and Nik Vale, CTO, this all-new system will streamline operations for affiliates and deliver a faster, more intuitive experience for instructors and students alike.
Key Features:
- Certification Wizard for simplified, faster certification processing
- Custom Booking Forms that integrate directly with school websites and AmericanSailing.com
- Instructor Management Tools for tracking and organizing activity
- Performance Upgrades for speed and reliability
The feedback was enthusiastic, and we’re already collecting ideas for new features coming in the 2026 season.
Dock Party with Waterway Guide
We wrapped up the day in true Annapolis style—with an epic Dock Party co-hosted by Waterway Guide. Instructors, affiliates, VIP guests, and lucky passersby joined us for amazing food and drinks catered by local favorite O’Brien’s. The food was such a hit that people stopped us the next day to rave about it!
During the party, Jonathan announced our growing partnership with Waterway Guide. Together, we’ll be expanding our collaboration to deliver even more sailing content, safety resources, and adventure inspiration to your inbox soon.
See You in Annapolis 2026!
The 2025 Annapolis Boat Show reminded us why this event is such a cornerstone of the sailing community. It’s where ideas are born, partnerships grow, and friendships set sail. If you missed it this year, make plans to join us in Annapolis 2026. Whether you come to browse boats, meet our schools, or simply soak up the energy of the docks, you’ll leave inspired—and ready for your next adventure under sail.
