Solo Sailing

sailboatI can count the number of times I’ve been sailing, which means I haven’t gone out much. And today, with winds billowing at 15 knots, I certainly won’t be heading out to add to my paltry experience. I’ll leave these sorts of winds for later days, when I’ll need a calculator, not my fingers, to count the number of sails I’ve made.

Having my own sailboat, not sharing it in a partnership or with a spouse, means I have to handle the it alone. I prefer sailing solo than with someone else. Enjoying sailing my boat alone is comparable to riding a horse alone: instead of sharing the saddle with another and splitting the roles of power and steering, I get to do both.

Sail One

The first time I took the girl out was just to cruise around my little bay. Nervous at first, I kept telling myself I could do it. The winds were light and perfect, not at all intimidating, so I raised my sails. Thankfully the sail was uneventful, which is ideal for the first solo sail. I got to practice tacking and beam reaching, the funnest points of sail. The winds died about two hours after I started, so I started up my engine, dropped the sails, and headed back to anchor.

Sail Two

My second solo sail was a bit more fun–okay, a lot more fun. The winds were a little faster when I decided I wanted/needed to go sailing, and as I was getting everything ready to go, a fellow liveaboard, Jonathan, came by in his dinghy and asked if I was heading out. I responded with yes, and he got jealous. So I told him he should go sailing too, in his own boat. He didn’t need a lot of convincing, and in under an hour we were both out on the water in our respective boats. For the curious, Jonathan has a Cascade 36’. As a reminder, I have an Islander 30’.

That's Jonathan's main sail in the distance. He just raised it while I was out in the non-wind.

The winds died as soon as I reached the middle of the bay. There was a little wind to either side of me, but I was dead in a lull. Jonathan caught up with me under motor power and we decided to head out of our little bay in search of better wind.

We motored for a while, but as soon as we saw some rippling water, we cut our engines. We raised our jibs and got ready to race (Jonathan joked about racing earlier, and it’s common knowledge that whenever there are two or more sailboats in close vicinity, there’s a race). It took only a few minutes for me and my boat to pass Jonathan’s, and I pointed it out to him by yelling: “Does this mean my boat’s faster than yours?” to which he responded: “At least for today!”

Pulling away...

My boat was faster than his for all of the day. With each minute I put more distance between us, heading for dark, rippling water (wind!) to the west, which was blowing from the north. It was a light beam reach as we headed to the wind, and when we finally got to it, it was time to close haul and cook it.

Close haul, though not the fastest point of sail, feels the fastest, as you sail as closely to the wind as possible, so it’s blowing in your face. I tossed my baseball cap into the cabin before losing it, and should’ve tossed Riley down there with it, but didn’t. Riley wasn’t happy with the sound of my winches (self-tailing, thank goodness). Side note: On those rare occasions when Riley gets nervous, he seeks the reassuring comfort of his mommy by trying to be in physical contact with me with as much as his body as possible. Right now he’s lying in my lap, sleeping, even through the scary wind. He’s a mama’s boy, what can I say?

Starting to heel...

Anyway, there we were, tacking into the wind, heeling (leaning) and having a great time. Jonathan was way in the distance behind me, on the same tack as me, just a lot further back. Oh yes, this is me being a bad sport, gloating because my new boat and my green sailing skills were kicking his gluteus maximus. My top speed at close haul was 6.3 knots.

We got all the way to a bridge and the wind got flukey. I checked behind me and saw that Jonathan had turned his ship around and was running downwind, his sails trimmed to wing-and-wing. I checked the time and thought it was a good idea to follow him back home, so I could drop anchor before dark.

Jonathan running downwind, wing-and-wing.
Riley in the cockpit!

Heading downwind made Riley a happier dog, for though we were still speeding along at a healthy four to five knots, the wind was behind us and all was calm onboard. The problem with heading down wind is how particular the sails can be. Trying to catch as much wind as possible, the sails are sheeted all the way out, and if you’re not careful, the boom my gybe accidentally.

Jonathan’s boat was getting larger on our horizon as we got closer. And soon I was passing him again. Muhahaha! Then to head back into our home bay, we tacked and I was able to get some great photos of the dramatic sky.

Wicked cool sky as we came home.

I made it back the quickest, and was still under sail when Jonathan dropped his and motored back to anchor. I did the same once I got a little closer to my chosen spot, then dropped my jib and my main and tied everything up. To debrief, Jonathan had me over to his boat for tomato soup and bread, and he told me that I “killed it out there!” He spent a lot of the time at dinner searching for new sails, as he complained that his were little more than bedsheets.

Sail Three

A few days later I decided to head out on my own again. It was a Saturday, so Jonathan had to work at the port. I gloated about it before leaving in my newly christened boat, Libby. I cruised for a bit in the bay then got bored and headed downwind out of it. Since it was a sunny, gorgeous afternoon, there were lots of boats on the water, power, sail, and kayak. Sail three was when I decided I hate powerboats and the people who man them. That’s a separate post, I think, but I just wanted to mention it here.

We headed over to an island to spy on all the rich people and check out their million dollar homes. This time Riley was in the cabin, but I spoke to him so he didn’t freak out and think I was leaving him. Then, after doing as much as we could at the island, I looked west and saw tall ships. Booyah!

Tall ship off the starboard side!

I turned Libby around onto a beam reach and we headed right for the ships. They were putting on a demonstration and firing fake cannons (Riley hates loud blasts, so he wasn’t pleased) at each other in mock battle. Tall ships and cannon blasts are hard to miss, therefore every other boat, power or sail, in the vicinity came to see what was going on. Air horns sounded as the ships battled it out (that’s the boating way of saying “bravo!”) and many of us took our turns getting close to the boats for a better look. And since I live aboard, I have all my belongings handy, and snapped some photos and even took a short video.

After that, me and my brown-turning-red skin decided to head in and call it a day. When we reached a lull, I took the opportunity to drop my sails, tie up, and motor back into my bay. While motoring can be pretty slow, it charges up the batteries, which is always useful. It should be mentioned that it’s much faster to sail than it is to motor, so getting back home took me at least an hour.

It was a kick going solo sailing and seeing the tall ships duke it out. Sometimes I can’t believe how amazing life can be.

My next solo sail will probably be soon, if the wind dies down and it isn’t raining. Since I mopped the floor with him in our first race, Jonathan, who’d been talking about needing new sails for months, has put grommets in a new jib and ordered a full battened main sail! I think someone’s motivated. He’s ready for a rematch, so I need to practice up now that he’ll be sailing with proper sails. Any suggestions? I’d love to hold onto my title as fastest sailor.


  1. Grandma Rita September 24, 2011 at 6:43 am


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  5. Tom June 18, 2012 at 12:25 pm

    Hi Courtney.. thoroughly enjoying it! Will be joining you on the water very soon as a live-aboard. I will be on the great lakes for a year then off to the salt water. Keep writing, I’m eating it up!
    Fair winds