I didn’t plan to race boats. I thought it was for pros, or folks with fancy gear. Then a friend texted me on a Wednesday: “Want to crew? We’re short.” I said yes before I could overthink it.
His message had the little ⛵️ next to a beer mug—emoji shorthand that got the point across instantly. If you want to get fluent in what tiny icons can really say, take a peek at this illustrated rundown of sexting emojis where you’ll uncover the hidden meanings behind popular symbols and pick up ideas for making your own texts sharper, funnier, and way more expressive.
That one night changed how I see San Diego—honestly, how I see speed.
First splash: the Wednesday Beer Can Races
We met at San Diego Yacht Club. The sun was soft. The wind felt like a cool hand on my face. I got tossed on a J/105 with a small crew. Fast boat. Big main. Simple lines. My job? Rail meat. Sit on the high side. Lean. Move when told. Don’t fall in. Easy, right? These evening dashes are actually part of the San Diego Yacht Club’s J/22 Beer Can Series, an after-work tradition that welcomes newcomers and salty veterans alike.
Not really. But also yes.
We tacked toward Harbor Island. I heard “Ready about?” and then the boat snapped through the wind. My leg slipped on the first tack. Non-marking shoes matter. I wore Sperrys after that day, and never looked back. I also wore sailing gloves (Gill) because the jib sheets bite. And they do bite.
At the leeward mark, I helped with the spinnaker. It was a red chute—bright as hot sauce. The crew called “Hoist!” and that sail filled like a chest taking a deep breath. We took off. I could feel the bow start to hum. My cheeks hurt because I was grinning so hard.
We finished mid-fleet. I didn’t care. We shared a bag of chips on the dock and laughed about my messy line tail. You know what? It was worth every bruise.
Where to watch for free (and still feel the rush)
You can watch these Wednesday night races without a ticket. Bring a jacket, a hat, and time.
- Shelter Island Shoreline Park: You get close passes. Boats skim by like birds.
- Harbor Island Park: Wider view. Great for photos with the skyline.
- Cabrillo National Monument: Farther out, but the whole bay looks like tiny toy boats. Pretty at sunset.
Show up by 5:00 pm since parking fills fast. I sometimes park near Point Loma Seafoods and walk. Then I grab a shrimp cocktail after. Little tradition now.
Bayfair on Mission Bay: Loud boats, big grins
Let me explain something about hydroplanes. They don’t whisper. They scream. San Diego Bayfair rolls in each September on Mission Bay, and those H1 Unlimited boats fly. They sit on a cushion of air. It looks unreal, like they’re skimming over ice.
For an eye-opening taste of how powerboat competition plays out on a global stage, visit the XCAT Racing World Championship site and watch those twin-hull rockets shred water at over 100 mph.
I watched from East Vacation Island. The smell of kettle corn, sunscreen, and engine fuel mixed in the air. I wore foam earplugs (3M) and I was glad I did. Those engines pound your chest. I brought a small chair, a light hoodie, and cash for tacos. Easy day.
What I loved: the crowd. Kids waving flags. Old fans talking lap speeds. The pits feel like a garage meet-up, but bigger. You can see crews wrenching on the boats—sharp tools, quick hands, focused eyes. It’s very “race day” but still friendly.
What I didn’t love: long lines for food at noon, and dust on windy days. And the sun bounces off the water. SPF 50 (I use Sun Bum) is not optional.
The sweet beginner side: Mission Bay sailing
Hydroplanes are pure noise and speed. Fun, yes. But my heart went back to sails. I tried a Friday night race out of Mission Bay Yacht Club on a small keelboat. Short course. Mark roundings close to shore. It felt like a game of chess but wet.
We had a Catalina 30 behind us, chugging along like a steady uncle. A pair of Hobie Cats zipped past like kids on scooters. I learned to call puffs. “Dark water, starboard side!” I trimmed the jib and felt the sheet load. My hands buzzed.
If you’ve never sailed, the Mission Bay Aquatic Center runs classes (check out their sailing lessons page for schedules and prices). You learn knots, the wind clock, right of way. Simple stuff that saves you when things get weird. And they do get weird—kelp can wrap the rudder when you least want it.
Little gear that saved my bacon
You don’t need a closet full of fancy stuff. But a few things made my days much better.
- Non-marking deck shoes (Sperry or Helly Hansen): No more slips.
- Sailing gloves (Gill short finger): Your hands will thank you.
- Polarized sunglasses with a retainer (Costa + Croakies): The glare is real.
- Lightweight PFD (Mustang Survival inflatable): I forget it’s on.
- Buff or neck gaiter: Keeps sun off and you look kind of legit.
- Reusable bottle with a clip (I use a Nalgene): Clip it to something. Boats bounce.
Tiny add-on: a dry bag for your phone. Don’t ask how I know.
Long days on the rail will make your back knot up like a halyard snarl. When I was up in Kingston for a freshwater regatta, I discovered sailors trade not only weather apps but also massage intel—if your shoulders ever need untangling, check Rubmaps Kingston for a crowd-sourced map of local parlors, candid reviews, and pricing so you can loosen those knots before the next starting gun.
The little things I notice every time
San Diego weather lies in the morning. It looks gray. Then noon hits and the west wind fills in. On the bay, 10–15 knots is common in summer. That’s perfect for a fun heel and a tidy wake. In spring, plan for layers. Your teeth will chatter after sunset, no matter how tough you think you are.
I always throw in snacks. Gulls will eyeball you. I swear they know when you open a bag. Also, if you get seasick, watch the horizon and nibble ginger chews. It helps. Don’t hide it. Crew gets it.
Quick routes and bites
- Pre-race coffee: Jennings House Cafe in Point Loma. Cozy, no fuss.
- Post-race fish tacos: Mitch’s Seafood. Fresh and fast. Try the grilled mahi.
- Gear stop: West Marine on Rosecrans. Last-minute gloves or a whistle.
Side note: scooters near Shelter Island are fun after races, but be safe. Wet docks make for bad comedy.
What I didn’t love (and what I learned)
- Parking near Harbor Island after 5:30 pm? Good luck. Arrive early or use a rideshare.
- Diesel fumes around marinas can be thick. A mask helps if you’re sensitive.
- Boat heads (toilets) are… tiny. Go before you go.
- Crowds at Bayfair get packed by mid-day. Morning arrival saves your sanity.
I also learned to speak up. If you don’t know a knot, ask. If you’re cold, say so. Boats run better when everyone tells the truth.
A small, honest note on safety
I wear a PFD every time. No drama. I also tell the skipper if I can’t swim well that day. Sounds silly, but we all have off days. Hydrate. Eat. Sunscreen. Simple things keep your brain sharp when the wind kicks.
The magic that keeps me coming back
There’s a moment on San Diego Bay when the sun drops behind Point Loma. The sails turn gold. The water turns soft and dark like denim. A sea lion pops up, stares, and sinks again. The bow cuts a quiet path. And for a few seconds, time slows. That’s the good stuff.
Then the horn blasts, and it’s game on. Trim. Hike. Breathe. Smile. Repeat.
Should you try it?
Yes. Even if you’re nervous. Even if you think you don’t know enough. Start with a watch night on Shelter Island. Bring a sweatshirt. See how the fleet moves. Then ask a local club about a crew list. Many boats want new hands. Promise.
And if loud engines are your thing, hit Bayfair. Wear earplugs. Cheer like you mean it.
San Diego boat racing isn’t one thing. It’s sails and spray, tacos and tools, laughter