📞 Call Captain Shane: 443-615-4413
Crew Connect Racing

They Belong on the Water

Free community sailing. Real racing. Real opportunity.

Free Community Sailing · Annapolis & Baltimore

A Pathway to Opportunity — On the Water

Our Mission

Crew Connect Racing exists to build better people through sailing — giving underserved kids and adults across Annapolis and Baltimore a free place on a real team, where they find purpose and belonging, build character and skills, and earn a path to opportunity that runs from a first sail to the world stage.

Along the way, we open the sport itself — from a first sail to ocean racing — to everyone who has never had a way onto the water, and we use sailing, the original clean-energy sport, to raise awareness of the importance of clean energy.

Sailing is an open sport on closed water.

You need a boat.

You need a club.

Or you need to know someone.

A full crew working the deck of a J/105 racing on the Chesapeake

Eight people, every one of them working. This is the boat, and these are the jobs, that most people never get near.

Most people have none of the three — and the people competing at the highest levels of this sport still don’t reflect the communities around the Chesapeake. Age, gender, race, or income shouldn’t decide who gets to experience the water, become a sailor, and compete.

This team exists to change that — and to change who people see when they picture a competitive sailor. Participants sail free: no fees, no membership, no boat required; if you show up and do the work, there’s a place for you. They aren’t passengers on someone else’s team — they train, trim, drive, and race as the team itself, and the discipline, accountability, and confidence come from being counted on by a crew that’s counting on you. The path runs from a first sail all the way to offshore racing, with hands-on training and mentorship toward real maritime careers along the way: marine electrical and diesel systems, rigging, composites and boat repair, sailmaking, deliveries, paid crewing, yacht sales, and the path to a Coast Guard captain’s license — skills on the water that become opportunity on shore. A different kind of sailing program: a free community team built not just to get people sailing, but to compete at the highest levels of the sport with the community as the crew — and a sport that starts to look like the communities around it.

"Better people through better sailing."

Courage · Integrity · Compassion

Iron sharpens iron. We train and practice with real standards — not because winning is the point, but because the work of getting better is where better sailors, and better people, are made.

Crew Connect sailors at golden hour after Wednesday night racing
45 Sailors and Growing

The Demand Is Already Here

Through Crew Connect, 45 active members are already matched with racing boats across the Annapolis fleet — and every week more people ask to sail than there are boats to put them on. The interest isn't the problem. The bottleneck is the platform.

"We have more people who want to sail every week than boats to match them to. This program needs its own boat to grow."

Ten people. One rail. That's the platform we're raising for.

Free Sailing, Measurable Change

The Impact We're Building Toward

Real, measurable outcomes — economic and social change you can count, not just count on. First-season commitments:

50+participants, year one
40+free program days
$0to participate

50+ participants in year one: underserved and underrepresented kids and adults from Annapolis and Baltimore, sailing free — from first-timers to regular racing crew. 40+ free program days: on-water community sails, coached training sessions, and race days across a full Chesapeake season.

Pathways to real work: participants are trained and mentored toward the trades this industry hires for — marine electrical, diesel and mechanical systems, rigging, composites, sailmaking — plus paid crewing, deliveries, yacht sales, and USCG captain’s licensing — skills that become family-sustaining careers. Measured and reported: participation, progression, and outcomes are tracked and reported to partners and funders every season.

First Sail → Offshore Crew

The Pathway

From never-touched-a-boat to offshore crew — one earned step at a time.

01

First Sail

Free community sailing days on the Bay. No experience, no gear, no cost — life jackets and foul-weather gear provided. Just come sailing.

02

Learn

Coached training sessions: trimming, driving, teamwork, safety. The same instruction paying clinic sailors get — free for program participants.

Race

Wednesday night racing and Chesapeake regattas with participants in every position on the boat. Not a demo. The actual team.

4

Offshore

Distance and offshore racing as the team earns its way there — with the long-term goal of competing at the highest levels of the sport, crewed by people who started at step one.

The community is the crew.

Real boats. Real racing. Real opportunity.
What the Program Actually Looks Like

What the Program Looks Like

This is not a race team with a charity attached. It is a year-round training program that happens to compete. Across the season the boat runs on a weekly rhythm of work, learning, training, and racing — and every session is free.

Boat Work Nights

Participants maintain the boat they sail: rigging, electrical and electronics, diesel and mechanical systems, composites, sail care. Real trade skills taught by working professionals — ownership, accountability, and the habits a marine career is built on.

Classroom Sessions

Racing rules, weather, navigation, safety at sea, boat systems. Toward real certifications: US Sailing Basic Keelboat, Safety at Sea, First Aid/CPR, and captain's-license course guidance for the path to a Coast Guard license.

Weeknight Racing

Weeknight series racing on the Bay, with community participants as the crew — not passengers. Roles rotate so everyone learns every job: bow, pit, trim, helm.

Training Sails & First Sails

Regular coached on-water sessions for the developing crew, plus dedicated First Sail days for total beginners — no experience, no gear, no cost. This is the front door.

Bay Distance Races

Chesapeake distance and overnight races through the season: the step from round-the-buoys to offshore. Watch schedules, night sailing, real seamanship.

The Annual Offshore Race

One major ocean race a year (target: Annapolis to Newport) crewed by sailors who earned their place through the program. The season's summit, and the story that brings the next fifty through the door.

Off-season (December–February): classroom series, winter boat projects, frostbite racing on partner boats, and planning the next season with participants at the table.

What participants get: a real skill set (sailing, seamanship, boat systems), certifications with market value, mentorship from working captains and pros, leadership roles as they advance (watch captain, boat captain), all safety gear and foul-weather gear provided, transportation support for Baltimore participants, and a crew that expects them to show up — and notices when they don't.

One Boat. One Team. Open Doors.

An offshore-capable race boat that carries 8–10 crew is the platform for everything — community sails, training, and racing — with every mile documented by professional drone and film coverage.

A Life on the Water

The Miles Behind This

College offshore racing, Wednesday nights, the A2N win, deliveries — the program is built on thousands of miles of real sailing. Flip through.

Crew Connect Racing gallery
Captain Shane Kilberg
Who's Building This

Captain Shane Kilberg

I didn’t grow up sailing. I found it at a college club fair and, two weeks later, was racing for the top college offshore program in the country — pure luck, with no pathway behind it. That luck became a career: offshore racing, an Annapolis-to-Newport win, a Coast Guard captain’s license, and years coaching new sailors and connecting people without a boat or a club to racing crews through Crew Connect. I’ve seen how many people want in, and how few ways in exist. This program is the pathway I never had.

A2N Race WinnerAnnapolis to Newport
College of CharlestonOffshore Sailing Team
USCG 100-Ton MasterSail & Power
It's Working — Meet the Sailors

This Is Already Happening

“I didn’t have a boat or a club. I just showed up and did the work — and there was a place for me.”

Mark, 17 — Eastport

Mark racing on a J/105 on a Wednesday night

Mark on the rail of a J/105, Wednesday night racing, Annapolis.

Mark, 17, from Eastport, was walking the docks on a Wednesday night when he stumbled onto a J/105 crew heading out to race. He asked if he could come. Through Crew Connect, he’s now a regular — racing Wednesday nights, and recently taking his first ride on a foiling WASZP. “Crew Connect opened up a lot of opportunities,” he says. “I’ve done a lot more racing than I ever would have.”

Jeff, J/22 owner, frostbite racing on the Chesapeake

And owners are already opening their boats. Jeff owns the J/22 SomerSault and sails year-round — frostbite racing included — putting Crew Connect sailors on the water with him. It's exactly how this is supposed to work, and it's working.

But a J/22 carries three people, and our numbers are growing every week. To take everyone who's asking — and to train and race them as a real team — we need a larger platform, built for this on purpose.

What We’re Raising

Phase One — Build the Platform

Interest isn’t the problem. The platform is. Here’s what it takes to launch:

$355Kphase one
1boat
1full season
50+participants

Phase One capitalizes the entire first year — the boat that makes the program possible, and a full season of free programming on it. The boat is a one-time purchase that serves the program every season after; from year two the need is operating support only, and every funding milestone beyond that unlocks more boats, more coaches, and more participants.

What your support unlocks, milestone by milestone:

1
First Sail Days

Free first-time sailing days for kids, families, and adults who have never been on the water — the front door to everything else.

2
Weeknight Racing

A community crew racing the weeknight series every week of the season, coached, with real jobs on a real race boat.

3
Bay Distance Racing Team

Overnight and distance races across the Chesapeake — the step from round-the-buoys to offshore, on the team’s own boat.

4
Shorthanded Training Platform

Doublehanded and singlehanded training for progressing sailors: the discipline that leads to ocean racing.

5
Offshore Campaign

Community crew on the start line of Annapolis-to-Newport and Bermuda races, under the team’s flag.

6
Ocean Racing

Solo and doublehanded ocean campaigns that carry the mission — access, clean energy, better people — to the world stage.

$355K PHASE ONE
The Boat & Equipment — $175,000

An offshore-capable race boat for 8–10 crew, plus safety equipment, electronics, and loaner gear for participants.

A Full Season of Free Programming — $164,000

A full year of operations: coaching, dockage, insurance, maintenance, training, and race entries — participants pay nothing.

Administration — $16,000

Charitable administration and reporting while the foundation completes its 501(c)(3) approval.

Then Phase Two: a $600,000 raise for a dedicated ocean race boat in 2027 — taking this team, and this community, offshore.

This is where it leads.

Photo: Tim Mangus

The Long-Term Vision

Community → Offshore → World Stage

Every level of this vision grows out of the same community program — the ambition is the proof that the model works. Crew Connect Racing — a team like none that's ever competed before: underserved and underrepresented sailors from our own community, climbing to the top of the sport. Every stage grows the free community program beneath it, and each stage is funded before the next begins.

'26
RAISE: $355KBOAT: J/120

Launch — End of 2026

Acquire an offshore-capable J/120-class boat and launch the free community program: coached training, Wednesday night racing, Chesapeake regattas — with community participants as the crew.

Milestone: full first season sailed. Target race: Annapolis to Newport.

RAISE: $600KBOAT: CLASS 40

Ocean Racing — End of 2027

Step up to a Class 40 — the pinnacle of ocean racing short of the IMOCA fleet. Doublehanded and fully-crewed ocean races with crew developed from the community pathway, alongside the continuing Bay program.

Milestone: community-developed sailors racing offshore on a world-class platform.

BOAT: IMOCA 60

The World Stage — 2030

An IMOCA 60 campaign — The Ocean Race, and the Véndée Globe pathway — crewed by sailors who came up through the community program. Measurable social change for underserved communities, proven on the biggest stage in the sport. Every sailor aboard exists because someone opened the door years earlier. No team in the history of the sport will have been built this way.

Milestone: the first world-stage racing team ever built on philanthropy — from first free sail to the start line.

THE FINAL STEP

America's Cup

The Moneyball Challenger: the first amateur-rooted America's Cup campaign — not built to outspend, built to get real people from the community to the start line of the oldest trophy in sport.

A team made up of people this sport was never built for. That's the point.

Clean Energy · Our Second Mission

The Sport Runs on Wind. The Message Rides With It.

Sailing is the original clean-energy sport, and the water we race on carries an industry that burns the dirtiest fuel in common use. While we open this sport to everyone, we use it to raise awareness of the importance of clean energy. The way Turn the Tide on Plastic carried the ocean-plastic message around the world, our team carries this one.

“We need to reduce our reliance on burning oil for energy. If a race boat can cross an ocean on wind alone, the ships that carry the world can run clean too.”

200Mcars’ worth of CO₂ from ships, every year
> Germanyshipping emits more than the entire country
0gallons of fuel burned to race
Race on wind

Every mile the team sails, from Wednesday nights to the ocean, is powered by nothing but the wind.

Run clean

As the fleet grows, program boats move their systems to solar, batteries, and hydro-generators — the same technology the marine trades are hiring for.

Carry the message

Our campaigns race under the team’s flag to show what a wind-powered team can do, and to put clean, oil-free shipping in front of everyone watching.

Sail · Support · Partner

Get Involved

Whether you want to sail, support, or partner — this is the starting line.

Goes straight to Captain Shane. You can also call or text 443-615-4413.

Got it — thank you! I read every one of these and I'll be in touch soon. ⛵

Already Sailing?

Experienced sailors: the fastest ways to plug in today are Crew Connect and the clinic series.