30 Boats on the Line
The J/105 fleet in Annapolis is the most active one-design keelboat fleet in town. Period. About 30 boats show up on the line every Wednesday night. There is no other fleet — not the J/70s, not the Beneteaus, not the Melges — putting that kind of number on the water week after week.
The boat is 34 feet, fast enough to be exciting, forgiving enough to learn on, and old enough that you can buy one for under six figures. The class rules keep costs reasonable. The racing is tight. And the community around it — the dock beers, the rivalries, the crew swaps — is what keeps people coming back year after year.
But if you talk to the owners long enough, one problem comes up again and again.
The Crew Problem
I've heard it from a lot of J/105 owners: finding and managing crew for the season is the hardest part of campaigning the boat successfully. Not the sail inventory. Not the rig tune. Not the bottom paint. Crew.
Sailing is a niche sport. Racing sailboats is an even smaller niche within that niche. And the numbers nationally are trending the wrong way — fewer people getting into the sport every year. It's expensive, the learning curve is steep, and unless you grew up at a yacht club, there aren't a lot of obvious entry points.
So you end up with boat owners who have $60,000-plus invested in a race boat, sitting at the dock on a Wednesday night because they can't find a fourth crew member. Meanwhile, there are people all over Annapolis who would love to race but have no idea how to get on a boat. There are crew listings and online resources out there, but there's a difference between finding a name and building a crew that actually shows up together all season.
That's the gap I've been trying to close.
Enter Jahn Tihansky
Jahn and I have been friends for several years. When I first reached out to him, he was the head coach of the Naval Academy's offshore sailing program — a position he held for 19 seasons. Four Kennedy Cup wins. Countless offshore miles. He's sailed and coached at virtually every level of the sport.
More than that, he's the kind of person everybody respects. Calm. Direct. He doesn't yell. He watches, he processes, and then he gives you one thing to fix that changes everything. When I was new to the Annapolis racing scene, Jahn gave me guidance that shaped how I think about sailing. He's done the same for hundreds of sailors.
When I started putting together the idea for structured fleet coaching, Jahn was the only call I made. He was in.
"Everyone respects Jahn. He has more experience coaching and sailing than almost anyone in Annapolis. He's done it all."
How the Clinics Actually Work
Ten sessions, April through September. Monday and Tuesday evenings, alternating every other week. Here's what a typical clinic looks like from start to finish.
Before we hit the water, everyone joins a Zoom briefing at the dock. Every participant is assigned to their boat beforehand — owners bring their core crew, and we match additional sailors from the community to fill out the rosters. We talk through the objectives for the session, what we're going to work on, timing, where we'll meet on the water.
On the water, it's structured drills. Mark roundings. Tacking sequences. Spinnaker sets and douses. Starting line practice. Safety procedures. Everything from fundamentals to advanced racing technique, calibrated to each boat's level. Jahn runs the coaching from a separate boat with full visibility of the fleet.
Every session includes drone coverage. That footage isn't just for social media — it's the backbone of the debrief.
After we're back at the dock, everyone meets at a local spot for a classroom-style debrief. We watch the video. Jahn walks through boat setup, rig tune, tacking angles, starting sequences. You can see exactly what happened on the water from angles you'd never get from the boat. It's one thing to feel a bad tack. It's another thing to watch it on screen and understand why it happened.
The one thing most recreational racers get wrong: Communication and consistency. There needs to be a method for everything you do on a race boat. There's an order of steps for tacking. An order of steps for taking down a spinnaker. The clinics are built around creating repeatable systems that work under pressure — so when it's blowing 18 knots and the windward mark is coming up fast, everyone knows exactly what to do without being told.
Who Shows Up
The core group is J/105 owners bringing two or three of their regular crew — getting the team to three or four people total. Then we match additional sailors from the community to fill out the boats. That's where it gets interesting.
An owner who's been struggling to find a reliable foredeck person all season suddenly has someone showing up every Wednesday, learning the boat, building the muscle memory. A sailor who's been wanting to race but didn't know anyone in the fleet is now on a J/105 with an experienced crew, learning from a professional coach, and building relationships that extend well beyond the clinic.
By the end of the season, the goal isn't just better sailing. It's a fleet with deeper rosters, stronger teams, and more people invested in showing up.
Crew Connect: The Bigger Picture
The clinics are the structured piece, but Crew Connect is the system underneath it all.
I built Crew Connect to add a hands-on layer to the process — personally matching sailors with boats, getting them into structured coaching, and building relationships on the water instead of just on a screen. The difference is follow-through. It's not a listing. It's a captain who knows the fleet putting the right people on the right boats and making sure it actually works all season.
Crew Connect is trying to fix that. We're creating opportunities for people who typically don't have access to the water — people who didn't grow up at a yacht club, who don't know anyone in the fleet, who assumed racing was something that happened to other people. The J/105 clinics are the platform that bridges the gap between wanting to get on the water and actually being on a boat.
This is personal for me. I have literally built a business with the sole goal of teaching people and getting people onto the water who otherwise wouldn't have the opportunity. That's the whole idea. The clinic is just the most visible expression of it.
Where This Goes
The goal for year one is to have 10 boats participating in the clinics. Year two, 20. Build from there. The J/105 fleet is the starting point because it's the most active one-design class in Annapolis and the boat is the right combination of competitive, accessible, and forgiving.
The long-term vision for Best Boating's racing program goes well beyond the clinics. We're working toward putting an offshore race boat on the water — competing in races like the Annapolis to Newport and the Annapolis Bermuda Ocean Race. A boat crewed primarily by amateur sailors, built around a community of people from all backgrounds. Youth sailors. Women in sailing. People who have had a harder time getting on programs.
That's the vision. The J/105 clinics are how it starts.
Get on the Water This Season
The 2026 clinic series runs April through September. Open to J/105 owners and crew at all levels.
View Clinic Details → Join Crew Connect →If You've Been Thinking About It
If you've been watching the Wednesday night fleet go out and wondering how to get involved — if you've been wanting to learn to race but feel intimidated because you don't know anyone — this is your answer.
Crew Connect exists for exactly this reason. The J/105 clinics exist for exactly this reason. You don't need to know anyone. You don't need experience. You need to show up, be willing to learn, and be reliable. That's it.
Call me. 443-615-4413. I will personally match you with a boat, a crew, and a program. That's what I do.
About Best Boating Annapolis
Best Boating Annapolis is a full-service boating operation run by Captain Shane Kilberg — USCG 100-ton Master, based in Annapolis. I sell boats, help people buy the right one, run private charters on the Chesapeake, shoot professional drone photography for yachts and regattas, handle mobile marine repair, and offer captain services for deliveries, training, and sea trials. The J/105 clinics and Crew Connect are the newest pieces — built to grow the racing community and get more people on the water. One captain, every service. If it involves a boat in Annapolis, I can help.
Captain Shane Kilberg
USCG 100-ton Master Captain. Sailing coach, and the person who answers the phone at Best Boating Annapolis. College of Charleston offshore sailing program.
More about Shane →