Beginning racing advice: recommended progression?

[fauxboat]

Asking for a friend:

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If you know someone who is contemplating in getting started as a singlehanded racer, starting from scratch, is there a recommended natural progression? EG racing crewed races, then doublehanded races, then racing singlehanded? Or is it just as good to just jump right in?

Would beginners be well served getting a smaller boat, such as a Cal 20 or El Toro, to hone their skills in before jumping to something bigger? Or is it more effective to just start on a 30' boat if that is what they intend to race long distances?

If the answer is in a FAQ, please send a link.

[Daydreamer]

I started out sailing an O’day 22, trailer sailer/lake boat.
Finding the SSS and this forum ignited the idea of sailing/racing on the Bay.

I knew nothing about yacht racing, and only know a little more now
So I volunteered for race deck. It was the Corinthian race with the starting line off of their deck.
I watched the starts and listened to the sequence over the vhf. I raised and lowered flags with Pat B.
Met several other terrific SSS members and had a great time. In the rain!

My first “race” was Round the Rocks. Not having a PHRF certificate I followed the fleet around the course.
It was windy, I was over powered but managed to get around the course.

I was hooked!

I raced Berkeley Midwinter’s after that and began to realize I wanted a bigger boat _/)__

Bought a Wilderness 30 in 2015 to go race on the ocean.
Raced SSS and OYRA for 3 years and SHTP in 2018.
Sold the Wilderness (wish I hadn't) thinking I was done.
Bought a B-25 a couple years later and am currently sailing/racing it.

I live 3 hours from the Bay and in the beginning didn’t know anyone. Showing up at a club to crew wasn’t an option for me.
Sailing and racing singlehanded has been my primary interest and the SSS along with this forum have been invaluable!
Andy Evans book, available on our website, has a great description for spinnaker handling solo.
I had never flown a spinnaker before the Wilderness and on a return from Drakes Bay was able to try it out. Successfully!

If crewing for others is an option, go for it!
Gets you out on different boats with people you can learn from.

If someone is looking for a first boat to singlehand, my only recommendation is to find one that inspires you.
If you don't look at it and go, man that is a beautiful boat!, then it will probably just sit.

[fauxboat]

Thank you Daydreamer for that great story.