How to Start Sailing with No Money

How to Start Sailing with No Money

I realized the other day that I should probably change the name of this blog to reflect this blog post’s title because at this point, learning to sail without spending any money is really what I’m focused on.

There are a lot of ways to go about it actually. People, myself included, have the mistaken notion that you need a lot of money to sail. Happily, I’m discovering that’s not necessarily true. I’m benefiting from the knowledge of seasoned sailors, using a little imagination and having the ‘ovum’ to pick up the phone and say, “yes!”

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sailboat update: part one

sailboat update: part one


seems like my dreaming of living aboard and working on my own sailboat is getting closer and closer to becoming a reality. the owners have returned from iceland and we’re set to talk tomorrow morning.

the boat, a 1977 C&C 26 seemed to be in decent shape when i saw it. although that’s still to be determined by an out-of-water inspection of the keel and rudder. the keel is reported to be blister free ::crossing fingers::

here’s the information i have about the boat’s condition at this point:

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junk rig love


This page will serve as a repository for all the information I'm gathering on the wonder that is the Junk Rig.

It appears to be designed with an older sailor in mind. With it's ease of reefing and other attributes that you can read about -->

The Junk Rig Association <-- for all things Junk. Amazing resource.

Why Should I Consider the Junk Rig... <-- this was the page that sealed the deal for me.


I want to share this life altering thing that's happening to me.

I haven't told many people about it. Fearful of negative reactions and judgmental assholes, I guess.

Although really, I don't give a shit what people think. I just don't want to spend time listening to all the reasons I shouldn't or I can't. I already know them and more. It's not going to stop me.

The sea, once it casts its spell, holds one in its net of wonder forever
— Jacques Yves Cousteau

This is how it happened.

I had just moved back to New York to care for my Mom. We were arguing while staying at her house in Sag Harbor. It's the house my great-grandmother built in the 30s. It's where I spent many a blissful summer as a child, just me and her. It's the place I most call home.

We were having one of those fights that are full of so much emotion and adrenaline and afterwards no one can remember what the fuck we were arguing about.

I realized I couldn't live with her every second of every day. I needed my own space but Sag Harbor was SO expensive. There just wasn't any way I could afford to rent anything...

and it came to me, this little voice, idea...

“…get a boat. live on it…”

It lit something up inside me. Some joyful place sat up and took notice.

Which was really, really odd cause I'm scared of the ocean. I'm not talking 'healthy respect', I'm talking - when I was a kid I had a vivid dream that a shark bit my leg off and ever since I've lived by the idea that the best way to prevent a shark attack is to stay the hell out of the water.'s a little phobia of mine.

The idea though didn't seem to care that it went against every story I'd told myself for the past 50 plus years.

“…get a boat. live on it…”

My rational self quickly piped in that I was over 60 years old and didn't know a damn thing about sailing!

“…I could learn...”

Oh shit! Memories of wanting to learn to sail when I was in my 20s came flooding back. My Dad, a sailor, invited me down to Florida to go sailing with him to the Bahamas for my vacation. It all went very wrong which was kind of typical and we never left the dock but I spent weeks learning what I could about boats so I could help crew.

Come to think of it, I actually had taken a dingy out solo and tacked my way around a lake one summer too many years ago. It almost capsized when I returned to the dock but without even thinking about it, I quickly shifted my weight to counter it. I always took that as a sign that I had some modicum of potential as a sailor.

Learning. Now there's something I love to do. Another lightning bolt hit me -- Oh my god! There's SO much to learn when it comes to sailing. The boat, the wind, the sea, how to sail, how to maintain equipment, how to repair equipment, the list just goes on and on...kinda blissful just thinking about the learning required actually...

Poor rational self. She took her last, best shot and reminded me that I had no money.

“…it doesn't matter...”

That's when I knew I was going to sea.