Here are a few tips, or things I think one should consider before buying a sailboat (or accepting a free one). With the exception of the “learn to sail” one, these aren’t necessarily mandatory; at least think about them before diving into boat ownership.

These aren’t unique, but they immediately came to mind when I was penning my thoughts on sailboat ownership after selling my boat. So, I thought I would share them.

  • Learn to sail
    This may seem like common sense for those in the market for a sailboat, but I’ve seen several people take the leap without knowing their aft from their ebb. Poke around the waterfront, or the sailing forums online and you’ll find many claiming that the best way to learn to sail is by finding an old salt to “take you out” a few times. Nothing against sailing with old salts, but taking an accredited, basic keelboat class (US Sailing, ASA, RYA classes are widely available) will give you a taste of what sailing is like and a great foundation for a lifetime of learning. That structured learning coupled with some time on the water with an old (or young) salt, and you’ll be well on your way to becoming quite salty yourself.
  • Join a club
    If this is your first foray into boat ownership, being part of a sailing community is going to be a great asset. While I’m sure this exists at some marinas or town mooring fields. Boat clubs offer community in spades: Lots of helping hands, advice and opinions (sometimes too many). There are a lot of online communities as well, and I encourage you to participate there as well, but nothing beats spending time with people.
  • Know the costs, but don’t get too hung up on it
    Before purchasing a boat, you should understand what you’re getting into. There are a lot of expenses beyond the boat itself. Do some research and estimate your annual all-in costs, including maintenance, insurance and storage. Don’t forget any upgrades you might want like new canvas or a really sweet sound system. That being said, tracking every cost down to the penny probably isn’t a good use of your time and certainly won’t add to the enjoyment of your sailboat.
  • Look for a boat that fits your style and region
    Budget is important, but not the only thing you should consider when looking for boats. Also think about the kind of sailing you’re going to be doing and where. A 42 foot, blue water cruiser isn’t necessary if you’ll be day sailing on a lake. Bigger boats come with more systems to maintain–an unnecessary headache when you aren’t using them.
  • Remember, it is a lot easier to buy a boat than to sell one
    Even beautiful and fairly priced boats can sit on the market for a while. Remember, this is not an investment, and it is far from liquid.

Photo of a small sailboat with an American yacht ensign flag at the stern, sailing at sunset, near the shore.
Champagne sailing on SV Uno.

While the sale of the boat is fresh in my memory, I wanted put a few thoughts down on my experience as a boat owner over the last four years. There’s a lot about the experience I enjoyed, and a couple things I didn’t. These notes are here to help guide me in the future if and when I decide to look at buying another boat. Perhaps, they will help someone else too.

What I really liked

  • Sailing!
    Obvious, perhaps, but must be mentioned. Lots of good times on this sailboat. We won some races, and lost some quite spectacularly. We anchored out and watched fireworks. We explored Jamaica Bay. There were more champagne sails than I can count. You don’t always know beforehand when you’re going to have a truly great sail, but you can feel it when you’re out there.
  • Flexibility/single handing
    With your own boat, you can do pretty much whatever you want. I spent several years at sailing clubs, which were wonderful. But, one usually needs to give up a little flexibly to have a smooth running club. Generally, you won’t be able to take a boat out at odd times or for a whole day. Single-handing is also verboten at the clubs I know.
  • Making it my own
    Don’t like the way something is rigged? Change it! Don’t like how that ding in the fiberglass looks? Patch it! Setting things up your way, perhaps with some trial and error, is one of the best parts of owning anything. Learning how to do things like eye splices and soft-shackles are not only useful skills, but very satisfying. I also didn’t mind doing small maintenance or repair projects, so long as they were within, or a bit of a stretch away from my skill level.

What I didn’t like

  • Hauling Out
    Hauling the boat (and putting it back in) bothered me more rather than less over the years. To the point that it became one of the reasons for selling the boat. Most people seem just fine with this activity, so I’m not sure why it caused me so much anxiety. Perhaps it was because I couldn’t do it on my own and I needed to ask for help. Next time, I’ll plan and budget for putting it at a yard and have them deal with it.
  • Sanding the bottom
    Sanding is terrible, nobody likes it. Some hate it more than others. The boat came to me with many, many layers of bottom paint, much of which I sought to remove. This meant a lot of time under the boat, at weird angles, getting covered with toxic paint dust despite my efforts to contain the mess with a shop-vac. Even with help, it took me a few sessions to get reasonably smooth. Painting was a joy compared to the sanding. In the end, sanding and painting a few times taught me a valuable lesson: Pay someone else to do it. The cost was worth every penny.

One thing I didn’t mention above was the cost. While I didn’t love spending money on maintenance and operating expenses, I understand that things do cost money. Advice to my future self on costs: Set a realistic budget that you’re comfortable with, then try to stay within that budget, roughly. Don’t track every penny–spend the time and energy you’d devote to expense tracking on sailing instead.

Soft shackles come in handy all over the boat. While every stainless shackle on Uno hasn’t been replaced with dyneema, soft shackles are increasingly being used. Among other things, I use them to attach the genoa sheets and in the downhaul on the boom. They are strong and light–although shackle weight isn’t a primary concern on Uno. I even carry a few extras for emergencies.

All manner of soft shackles can be purchased at the local yacht chandler. However, I prefer to make them myself. I’ve tried a few different styles and favor the “improved soft shackle” from the video below for its ease of operation, strength, and clean look. It is more time consuming to make, but I think it’s worth it.

I change a couple things from the tutorial. First, depending on the need, I’ll change the length. 40 inches of 1/8″ amsteel will make a ~2.5 inch finished shackle using the other measurements in the video. By the way, this is probably the minimum usable size for this type of shackle. To make bigger shackles, add more line (e.g. 41″ of line will make a 3″ shackle). I also taper the ends more than he does by taking out a couple extra strands at 1/2″ from the end.

This summer, some sailing buddies and I chartered a boat in Newport. As with other charter experiences I’ve had, it was spectacular.

Adam and I were co-skippers on this one, and it was thoroughly planned. Upon our return, we jotted down this list of things to think about next time around based on our experience.

This is not an exhaustive bareboat charter planning or passage making guide. Think of it as short addendum to the many guides available both in print and online.

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