How Much Sailboat Do I Need?

How Much Sailboat Do I Need?

Okay, you’ve checked out of 101, 103 & 104 and the sailing fever is still burning strong. You need to either check into a hospital or buy your first boat – you choose the latter. But what kind should you get? The magazines and websites have you drooling over boats that have tempted you with their sex appeal or indestructible capabilities and you are leaning in every direction.

I could cross the Atlantic on that thing,” you hear yourself saying as you scroll through the pages of YachtWorld. Yes, this is true, but are you going to cross the Atlantic? You’re nodding yes, but you’re not. This is the ghost of Christmas future and you’re not. The boat isn’t going to go near the Atlantic – it’s never going to go 40-miles from your dock and that’s ok! It’s more than okay. That’s the thing – assessing what the boat will most likely be doing informs what boat to buy. A potential buyer needs to be honest with themselves about their sailing intentions and find a match based on that honesty.

It’s true many don’t quite know what the future will hold and if that’s the case then buying “more” boat might not be a bad idea, but making a purchase based on outward appearances or a false identity could be a mistake. Most people think Open 60s look pretty cool but teaching Sally and little Danny to daysail on it might not be a perfect fit…

“Sally adjust the canting keel! Danny, do you know what you’re doing with those backstays? For God’s sake, we’re about to tack and someone needs to deal with the water ballast tanks!!!!”

An extreme example but, on a much lower level, this type of reasoning happens all the time. People compromise the element(s) they most need for one that they may hardly use, but like the thought of.

For instance, hearty boats designed for blue-water cruising can be expensive and sometimes a bit less livable because they have to accommodate for open ocean conditions and situations. Above all else, they have to be durable and resilient. “But don’t we all want durable and resilient?” Yes, of course, but most good cruising boats are plenty durable and resilient for coastal cruising situations and will provide more opportunity for dockside and at-anchor type scenarios.

How Much Sailboat Do I Need?

Think about what kind of sailing you’ll be doing, the time you’ll be spending on the boat and what you can afford. Lot’s of people like the look and idea of wooden boats but the cost and time to keep them solid and presentable can be intimidating and they are not always the most luxurious. Do they look amazing – yes. Is it like nothing else to feel the weight of a beautiful wooden cruising boat galloping through the water? That’s correct, it’s awesome. But they are not for everyone.

Both the wooden boat and Open 60 examples are heavy-handed – think about the ideal in a more subtle way. How many people will I normally be taking sailing? If you’re honest, will it come down to just you and Danny most of the time? Yeah? Then get something smaller (and cheaper) that will scratch the itch and get the job done. How much time can I realistically carve out to go sailing? If it’s a lot, then a boat you can grow into is a good idea, if it’s once a month or less, think about boats that will do well without a ton of regular maintenance and use.

If you go through a broker, let them know where you stand. They may want to cater to the dreamier side of your personality but if you know who you are and how you will likely use this boat, you’ll be a much happier sailor in the long run. It’s like making a long crossing – an honest and true assessment of the situation coupled with a pragmatic strategy will see you through to the best possible outcome.

If you’ve already bought your first boat, let us know if you think it was the right or wrong choice and why.

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We were looking for a used boat as our first sailboat. Rare that you find exactly what you target in the after market. Need to have a range. We ended up getting a bigger boat than we targeted, and it turned out well. Of all our criteria, there was one that was inflexible. The boat could not be more than my wife and I could handle for coastal cruising, without additional crew. Although we ended up with a bigger boat than the plan, it had power winches and roller furling on main and jib. We determined after discussions with experienced… Read more »

First boat 1980 22nd Catalina….love it great boat to learn sailing and repairs

Mary Kay
Think about where you want to sail and store your boat. Draft is a consideration — and if you get a boat that’s large it will have deeper draft and limit the available slips. We are on the Chesapeake and a 4′ draft is great. Also think about the docking procedures. Bringing our 1982 Catalina 27 into its slip — with expensive boats on either side we must avoid hitting — is challenging in strong wind. We are glad it isn’t 35 or 40 feet long! Like the Cat 22 owner below, we are glad we have a boat with… Read more »
Katherine Thomason
My sweetheart and I bought a 1961 Pearson Triton for $3,800. It is a “plastic classic” with only 250 made in Sausalito, and about 750 made back in Rhode Island. We have never regretted the purchase. With a monthly slip fee of $250, totally affordable. We sailed it in the SF Bay, mostly the Carquinez Straits, for almost a year before actually deciding to get sailing lessons. I’ve taken 101 and 103, but my sweetheart also took 104 classes….he’s a brilliant sailor! Our boat is perfect for the SF Bay, but someday we may opt for something a little bigger… Read more »
Doc Snooze

I feel like you’re my AA sponsor and this is my first meeting. You’re exactly correct, of course, and I still don’t know if I’ll take your advise. Not because I challenge it, but because the pull of “People compromise the element(s) they most need for one that they may hardly use, but like the thought of.” You nailed it, there. My name is Sean and I’m a feature-a-holic…

Having only two hours of “true” sailing experience I went looking for a boat to keep on the Chesapeake Bay (Rock Hall). One I liked was a 34 Hunter that the broker in actually talked me out of. He recommended a nicely prepared (good diesel, new sails, very good survey) 1985 Catalina 27. He essentially said, “I want you to come back in 5 years and by another boat. To do that, you need to learn on a boat you’ll be comfortable with.” Couldn’t really argue with that even thought it was a little smaller than I wanted. 3 years… Read more »
Les Ismore

Been sailing off and on for 30 years but never owned a boat until 2016. My dream boat? A 1978 Boston Whaler Harpoon 5.2… We use it every weekend and love working on it as well.

Will Lilienthal
I have sailed and owned many,many sailboats growing up. Granted, most of these boats were trailerable, daysailers in the 14ft range. I had always dreamed of bigger boats. But, being the cautious and frugal person I am, I decided to upgrade into a slightly larger boat. One that I would keep in a slip at a local marina. I made this transition thinking this is going to be the biggest mistake of my life or something I should have done years ago. Turns out, it was the best thing I ever did! That boat was a Lockley Newport 19′ with… Read more »