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Old 21-01-2022, 00:23   #1
GRH
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Need advice on first sailboat purchase

Hello everyone,

I’ve taken the basic keelboat course and plan on taking the basic coastal cruising course in April. I would really like to buy my first sailboat this Spring. All of my sailing during the next season will be on the Chesapeake. Ultimately, I’d like to pursue coastal cruising on the East Coast, learn the ICW route, and potentially offshore sailing.

So, I wanted to get some advice from you all on picking a first sailboat. On one hand, it certainly makes sense for someone with limited experience to keep it simple, maybe a Catalina 27 or 30, something that wouldn’t be too expensive to maintain, has a relatively shallow draft for the Chesapeake, and can be single-handed (also a big priority for me). However, given my long term cruising goals, I also think it would be great to purchase a sailboat that’s more capable of coastal cruising and even offshore sailing. That way I wouldn’t be working on maintaining a simpler boat for a few years just to inevitably sell it and buy a more robust cruiser. The most I can spend is $30K.

So, would something like a Pearson 365 Ketch be too much for a first cruiser? Or a similar cruiser with a cutter rig? I worked as a professional pilot for twenty years, and I take this all very seriously in terms of studying and being safe on the water. So, in a nutshell… keep it simple or go for a boat I can grow into as a sailor for the next ten-plus years? Really appreciate all your helpful replies.
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Old 21-01-2022, 00:36   #2
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Re: Need advice on first sailboat purchase

Gday GRH, do you have a local sailing club nearby. Great way to meet new people and see if you can join as crew on a casual racing dayd. Here in Oz we often have a Wednesday or Friday social races where skippers are always looking for crew, novice or experienced. Great way to see how a boat works in all winds and see what works for you.

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Old 21-01-2022, 00:58   #3
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Re: Need advice on first sailboat purchase

Hi Ozsailer, yeah we do have a lot of clubs here in Annapolis, MD. That’s great advice. I will definitely try get more experience on different boats, either cruising or racing, before I make the purchase.
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Old 21-01-2022, 04:42   #4
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Re: Need advice on first sailboat purchase

Keep it simple and get the boat you need now.

Bigger boats are more expensive to own and maintain, and your efforts are more about keeping the systems in good repair than sailing it.

Get a smallish Hunter or Catalina, and take it out every weekend. You're in a great area for sailing, and you can get a lot of sailing bang for the buck if you do it right.
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Old 21-01-2022, 05:03   #5
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Re: Need advice on first sailboat purchase

Quote:
Originally Posted by letsgetsailing3 View Post
Keep it simple and get the boat you need now.

Bigger boats are more expensive to own and maintain, and your efforts are more about keeping the systems in good repair than sailing it.

Get a smallish Hunter or Catalina, and take it out every weekend. You're in a great area for sailing, and you can get a lot of sailing bang for the buck if you do it right.
This here is the best advice. Buy a clean boat that's fully functional with decent sails and you'll sell it in a few years for near what you paid. Then you'll know more about what you truly want and need and will have a better insight into the care and feeding of the many "systems" a larger vessel has.
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Old 21-01-2022, 05:29   #6
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Re: Need advice on first sailboat purchase

I think that boat ownership is an evolution of sorts. You buy a boat. You start the learning process (how to sail it, how to fix it, how to anchor, how to navigate, etc.).

Most importantly, you learn what you like about your particular boat and what you don't like, and you start making a mental list about what features you want in your next boat. Maybe: roller furling, bigger anchor locker, better engine access, side loading fridge, pullman style berth(s), keep-stepped mast, bowsprit, dry head, bigger cockpit....all of the above, none of the above.

The point is, no one gets it "exactly right" on their first boat. Buy one that you think fits the bill, sail it, learn from your experience, figure out what works for you and what doesn't work for you, and evolve as a sailor and as a boat owner and then move on to your next boat. Bigger, smaller, different, but better for you and for your needs.

I think that would be a good approach for you. (It also would take a lot of pressure off you -- you don't have to worry about making the perfect choice in boats. You just have to make a good choice based on what you know now. But ultimately you know that it's just a temporary choice that you will probably be moving on from in a few years. So you won't be stuck in a paralysis-by-analysis situation that happens when we overthink something.)

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Old 21-01-2022, 05:33   #7
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Re: Need advice on first sailboat purchase

The Catalina 30 would work for both learning in the Chesapeake and coastal cruising. At 5.25' it is slightly deeper draft than ideal for gunkholing the Chesapeake but still very workable. At the same time very roomy for a 30' boat so adequate accommodations for cruising.

A $30k budget will be a bit tight but there were a lot of Cat 30s built so with some patience you will probably find one in decent shape for that. It would take a good bit of luck to find a P36 in decent shape for $30k but it sometimes deals happen.
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Old 21-01-2022, 05:43   #8
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Re: Need advice on first sailboat purchase

I second the previous 2 posters.
I learned to sail on my family’s boats so was familiar with sailing. My first boat was a Catalina 30, it was in good shape when I bought it but like every boat it needed some repairs and the usual rebeding of deck fixtures ect…. It was the perfect boat for long weekends on Lake Champlain. When we decided to move south and live on a boat we knew we needed something different. We sold the Catalina after 3 years of ownership for the same price we bought it for.
I think the Pearson 365 would be a good boat for your long term plans but not as maneuverable and easy to sail as something smaller.
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Old 21-01-2022, 07:19   #9
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Re: Need advice on first sailboat purchase

I like the Pearson 365 idea (my boat is a Pearson 367 - cutter rigged and deeper draft than 365). But I bought my boat when I already had years of sailing experience on dinghies and a Catalina 27. The Pearson 365 is not too much boat for a beginner, though it will feel that way at first. If you go that route, hire an instructor to help you learn docking and leaving the dock - those are the two most stressful things in sailing for a beginner, but with proper knowledge and practice, they don't have to be. I am a little skeptical, though, of what you can find for $30K amongst the 365's and 367's on offer. You DO NOT want a project boat as your first boat unless you simply LOVE working on stuff. If you can find a clean 365/367 with good engine, no (or few) leaking portlights, working depthfinder and wind instruments, okay. Chartplotter can be handled via a tablet / iPad if it is not present / working. Otherwise go with the Catalina 30 or equivalent. And do sail with other people at a local sailing club.
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Old 21-01-2022, 07:20   #10
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Re: Need advice on first sailboat purchase

You could buy a pearson 26 for a lot less than $30,000 maybe even for less than $3000. And like others have said sell it for a couple years and then move up to a bigger boat. The P 26 has a great reputation and lots of supporting owners out on the Internet.
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Old 21-01-2022, 07:26   #11
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Re: Need advice on first sailboat purchase

My first boat was a Catalina 30 - kept it for about four years and sold it for slightly more than I paid for it. Sailed it all over the Chesapeake, single handing it probably 30% of the time, including some extended cruises while between jobs. Mine was a shoal draft keel of 4 ft with a tall rig. It's a great boat, roomy, and easy to learn sailing and maintenance on it. Also there is a great online owners group that will answer all your questions.
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Old 21-01-2022, 07:54   #12
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Re: Need advice on first sailboat purchase

My nephew got on EBay and found a Cal31 up for bids. He picked it up for under $3K. OK, we were able to "board" the boat (without permission) as it was in our local harbor. Was well maintained by the yard, came with parts, equipment and good sails, and to my astonishment 183 hours on the motor. It was accurate, it was a new universal! So there are bargains out there for a first boat. While 31 feet scared him at first, they quickly learned to handle it comfortably. Great way to save money toward next upgrade.
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Old 21-01-2022, 07:54   #13
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Re: Need advice on first sailboat purchase

GRH, people with boats almost always looking for crew, so as mentioned earlier, getting experience on others boat can help to shape your needs/requirements. I learned how to sail many yrs before owning my first boat which was a 16ft day sailor. First keel boat was a 1984 Catalina 27 for $5000...that was in good shape back 7 yrs ago. Sold her for $3500...Sailed all over the long island sound (LIS), learned about elementary systems, boat maintenance, winterizing a diesel... wouldnt take it off shore, but for coastal cruising it was excellent. She drew 4 ft which was also important given the rocky coast & shallows in LIS. Looked at Pearson 34's, sturdy boat from the 1980's...never sailed the 365 ketch, so cant give you any direction there. My recommendation...look around for a Catalina or Pearson or Hunter or Ericson in the 27 - 30 ft range, 30+ yrs old...sail the heck out of it....do as much maintenance & repair on it as possible and sell it after a few yrs for your next boat..enjoy the hunt. Also be aware that your slip & winter storage fees will most likely exceed the price of one of these boats I've mentioned after 2 yrs..
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Old 21-01-2022, 08:07   #14
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Re: Need advice on first sailboat purchase

The first yacht will soon be too small. The second yacht will be about the right size and the third will be too big and expensive to keep.
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Old 21-01-2022, 08:18   #15
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Re: Need advice on first sailboat purchase

Start with a sailing club membership and sail, sail, sail.

You will make sailng friends, see other sailboats in action, and develop key skills. When you outgrow the club, buy a boat and... Go!

My opinion after teaching cruising for 40+ years.
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