Teresa Carey Words 13 Comments

One of the criteria that Ben and I had for boat shopping, was that the new vessel had to be big enough to take passengers aboard yet still small enough so that we can solo sail. Ben and I both solo sailed our pocket cruisers side-by-side for several years. When I compare that experience to all the other sailing I’ve done: dinghy racing, yachts, schooners, etc. No experience compares to what I gained while solo sailing. I’m not referring to a daysail or an overnight. To fully grasp solo sailing, it had to consist of owning my own boat, maintaining it myself, and long-term cruising both coastal and offshore.


I was sad to sell Daphne and leave behind not only that experience, but the sense of identity that went along with it. So, I asked Ben that we make it our goal to create solo time for each other. He agreed whole-heartedly. We would try to plan a few weeks each year where one of us would get off the boat while the other traveled solo, taking all the safety steps for solo sailing including informing the insurance company, making a float plan, and checking in.

It wouldn’t be enough for one of us to simply hide in the cabin while the other does all the work. That is not solo sailing. That is watch-keeping. When things get rough, a prudent sailor would use every resource aboard – meaning the smart thing to do would be to call on the other person for assistance. However, if you were sailing solo, and no one else was on the boat, the additional resources aboard are only within. Without solo sailing, those reserves of courage, physical strength, and wisdom are never tapped. That is why I see solo sailing as the pot at the end of the rainbow. No one ever believes gold is actually there, so we are content to delight in the rare beauty of a rainbow, or double rainbow without making the long trek to the rainbow’s end. But I know the impossible is possible. Especially when it comes to human capacity.

Without solo sailing, those reserves of courage, physical strength, and wisdom are never tapped. That is why I see solo sailing as the pot at the end of the rainbow. No one ever believes gold is actually there, so we are content to delight in the rare beauty of a rainbow, or double rainbow without making the long trek to the rainbow’s end. But I know the impossible is possible. Especially when it comes to human capacity.

I was honored to learn that both Ben and I had been nominated to receive the Ocean Cruising Club Jester Medal. The Jester Medal is awarded for an outstanding contribution to the art of single-handed sailing by a member or non-member of the Ocean Cruising Club. The co-chair of the OCC Award Comitee contacted me directly to congratulate me for the nomination and express appreciation for my insistence in simplicity in sailing. She said, “the judges all felt that your entry deserved real merit.”

Congratulations to the rest of the nominees and especially to the winners who are the originators of the actual Jester Challenge, namely Ewen Southby-Tailyour and Trevor Leek.

So, tell me. What do you think of solo sailing? Have you tried it? Never want to? Do you think I’m crazy? Please share you thoughts in the comments below.


Come aboard and set sail with Ben and I! We are offering New England and Nova Scotia Sail Training expeditions this summer.

Comments 13

  1. Lowell Monette

    I’ve only sailed a small amount and never soloed, although it kinda was because my “crew” hardly know what a sailboat was. … I’m all for solo sailing and being able to do so even if you’ve never done it. I also think “simple” is better. When the electronics fail, and they will, you’re back to simple anyway. So, why not just start simple. I also have to philosophy that if I can’t fix it I don’t need it on the boat. … You’re not crazy … you’re what sailing was ment to be.

  2. Martin

    Congratulations on both of your nominations! I’ve soloed in a tiny cat boat dinghy. but I don’t think of it as the solo sailing you are talking about. I think I would benefit greatly from the experience though. I’ve never been on a boat that I felt like I could solo. I am very inexperienced but, to me, changing the jib and steering don’t happen at the same time. I guess I need more practice to figure out all the tricks. I wonder if there is a sail trainig expedition I could go on?

  3. Viki Moore

    I think that is a great idea! I am a solo sailor who last year hooked up with another sailor and I can totally relate to your idea. I have had my yacht for 11 years and now we are currently looking for a bigger yacht to buy together to sail around the world, but it has to be small enough for us to be able to handle it alone. Some of the best and most memorable experiences have been while I was at sea alone. It is so empowering!

  4. Dorothy

    Congratulations on your nomination! When I had sailed with Fred for a week each summer on his 27-foot O’Day for about 8 years, I decided I wanted to take it out by myself. I felt that was the only way to really know what I did and didn’t know, and to actually, 100% myself, make the many decisions that need to be made even in a daysail. Fred was very kind to turn me loose alone on his boat. I will never forget those first couple of solo sails – the sense of pride, accomplishment and empowerment I felt, as well as the knowledge, skill and judgment gaps I uncovered. Those solo sails were a transformation point in my sailing.

  5. Nigel Doyle

    Single-handed has always fascinated me and I would love to do it. I don’t own a boat but I charter in the UK. Just passed my Coastal Skipper course and gathering experience all the time. But obviously I cannot charter single-handed so I’ve got to buy a boat if I want to do this. As Martin said in the post above (or below) it would be very interesting to go on a single-handed course. What a niche market, but fascinating too. Looking forward to the movie, folks. Can’t be long now, right?

  6. Chris Troutner

    Good on you!

    I’m sure that while you’re doing it, in the back of your mind, you’ll be thinking “this would be so much easier if Ben was here.”, and I’ve no doubt he’ll think the same.

    I imagine off-shore solo sailing is a lot like childbirth. It’s hell while you’re going through it, but the memory is fond looking back. I’ve never done either, so I wouldn’t really know.

    I do know, from my extended in-shore sails, that after a few days of sailing time slows down, the world shrinks, and life starts to make a lot more sense. Any way you achieve that mental state, you should. I certainly try to capture it as much as I can.

  7. Shea Devine

    To nominate you for a jester award is a joke. Blonde Hasler was a WW2 commando, invented and developed the the Windvane self steering mechanism, pioneered the junk rig for ocean sailing and bece synonymous with long passage solo sailing – crossing oceans single handed and sailing for many many days alone.
    Your bubblegum blog about minimalism and sailing in tandem with your boyfriend up and down the US Coast does not even come close in comparison. Your nomination de-values the award and makes a mockery of the organisation.
    This is not a personal attack on you.

  8. Frank

    I don’t know why some people take the time to write nasty comments, maybe …

    I really like your blog, it gives a warm description of sailing and cruising. I’ve sailed solo for many cruises, mostly coastal, but on the St-Lawrence Gulf around Gaspesie and New-Brunswick.

    Good luck with all your projects.

  9. Shea Devine

    Further to your comment please explain to me your understanding of why and to whom, the jester award is given. Then, within that context, please explain why my statement is unfair.

  10. Aaron Cope

    First, I love your posts and admire all you do. My very first solo sail was at the mouth of the Chesapeake. I got caught in a summer squall, unreefed, and then the jib furling jammed. I was crawling up the deck with the rail in the water, being pelted by rain. All I could think was, “This would be a ludicrous way to die!”. I finally managed to heave to and catch my breath. It was one of the best days of my life!

  11. Erik Barkefors

    Congratulations on your nomination!
    I’ve been sailing since I was little and tried different sizes of boat and crew. Now that the children left home, I have a 7.7 meter Swedish Maxi. It works great to sail solo in and I’m often out on day trips in the Swedish archipelago and open water in the Baltic Sea. Perhaps I will try longer races but then my current boat a bit too small.
    It’s fun to read your blog and see how others solve the everyday problems that always comes when you do something on your own. Thanks for the tips I received!
    Erik Barkefors
    Oxelosund Sweden

  12. Steve

    Hi Ben, Teresa,

    I think the nomination is fantastic and well deserved. Please ignore the unnecessary negativity.

    The award says nothing about requiring military service or the invention of new sailing technology. It’s about “outstanding contribution to the art of single-handed sailing”. I personally think you’ve done separately and as a married couple with your blogs, videos, training, public speaking and of course, the movie One Simple Question. You bring social media and attention to a potentially new generation of solo sailors. Well done.

    You both have inspired me to continue to pursue my goal of owning a sailboat and solo sailing. Thank you for all you do for sailing.


  13. Robert

    Hey Theresa, Ben,

    One nomination well deserved! You are true knights of the salt water. As Blondie Hasler was much more a solo sailing enthousiast than he was a commando, he would have surely preferred a “bubblegum blog about minimalism and sailing in tandem” over losing (almost all) his mates in France.

    I’ve just discovered solo sailing and it surprised me.
    When I’m sailing with my kids: I am constantly counting (them). Entirely my fault. When I’m sailing with her: I am constantly justifying. “Would you please steer one course, dear? Yes I see, but it makes my navigation so much easier.” But solo: (tada!) I am just sailing. Relaxed, happy and enjoying. Thought that would take half a lifetime, but it took just 5 minutes. The boat is 28 foot, 35 years and getting younger by the day. I heard her say “there is some more water round the corner there” and I think she is right.

    Hope you will be sailing together for very, very long.

    Kind regards, Robert

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