Advice on buying a sailboat.

CamilleHarris · 2026-08-21T11:39:13-0600

I’m thinking about buying a sailboat but I’m not sure which one to get. I don’t know much about boats yet but I’ve always loved them and I’m planning to learn how to sail. Does anyone have any good recommendations or advice?

Chris1956 · 2026-08-21T11:49:12-0600

You could start with a smaller sailboat with a jib and mainsail. That would be pretty easy to learn on. Say something less than 20 feet. They would have a sheet for the main, and a couple of cleats, likely clam-style for the jib lines. Get some experience with sail shape, on the small boat and it will pay off on a larger craft.

Larger sloops work on the same principles, but have more features like a traveler, self-furling jib (which is desirable), self-tailing winches etc.

tpenfield · 2026-08-21T11:54:13-0600

If you don't know much about boats, how do you know if you love them?

Depending on your budget and general skills . . .

Sunfish ( very basic but wet)
O'Day Dayssailor 2
There are a bunch of decent boats in the 15-19 foot range. Look at sailboatlistings.com to get some ideas.
Precision 15 or 18
O'Day 19

tpenfield · 2026-08-21T11:59:37-0600

Catalina Capri 14.2
American 14.6
West Wight Potter 15
Flying Scott
Hunter 14
Boston Whaler Harpoon

I'd avoid getting a Hobie Cat, as they are difficult to right if you flip them (you will)

southkogs · 2026-08-21T12:02:54-0600

If you're going to use a sailing school, I would look at the boats they use. A simple cat rig boat (like a Sunfish) is a great way to learn by trial and error. But if you get some instruction a sloop rig like Ted's list above is a good start too.

tpenfield · 2026-08-21T12:03:30-0600

Here is a link to my webpage about my Catalina 22 (sailboat)

https://www.tpenfield.com/Catalina22/

CamilleHarris · 2026-08-21T12:32:28-0600

Chris1956 said:
You could start with a smaller sailboat with a jib and mainsail. That would be pretty easy to learn on. Say something less than 20 feet. They would have a sheet for the main, and a couple of cleats, likely clam-style for the jib lines. Get some experience with sail shape, on the small boat and it will pay off on a larger craft.

Larger sloops work on the same principles, but have more features like a traveler, self-furling jib (which is desirable), self-tailing winches etc.

Honestly I’ve been looking at a 2018 Catalina 22 Sport a 2019 Beneteau First 24 and the MacGregor 26. But I haven’t found any newer MacGregor 26s. The ones I’ve seen are older models from 2010 to 2013. Would any of these be a good choice?

tpenfield · 2026-08-21T13:05:40-0600

Yes, as long as you are comfortable with the larger boats. Are you going to be day-launching or have the boat at a slip or dock?

tpenfield · 2026-08-21T13:06:30-0600

Mast raising is more challenging with the bigger boats.

tpenfield · 2026-08-21T13:10:50-0600

You will find that many of the boat brands are no longer in production (Macgregor for example).

CamilleHarris · 2026-08-21T13:23:02-0600

I plan to keep it at the marina after the boatyard inspection is complete. Raising the mast definitely seems challenging so I’ll take my time. MacGregor has indeed stopped production. For my first boat I’m planning to buy used. I think it would be better to upgrade once I have enough experience.

tpenfield · 2026-08-21T13:44:33-0600

Any of the boats mentioned should be fine. Perhaps take a course in boating safety and then if there is sailing instruction available, take that too.

IMO . . . The biggest challenge novice sailors have is sailing "into the wind" . . . many find that they can only go "down wind" and can't get back to where the started from.

CamilleHarris · 2026-08-21T13:57:19-0600

That’s great advice. If the wind isn’t in my favor I might never make it back lol. I’m not planning to sail directly out into the ocean. I’ll start by sailing on the rivers around Maryland.

Chris1956 · 2026-08-21T14:16:45-0600

If you plan to keep it in a marina, you will need a kicker to maneuver.

CamilleHarris · 2026-08-21T14:55:30-0600

Chris1956 said:
If you plan to keep it in a marina, you will need a kicker to maneuver.

I understand that. I have a friend who owns a sailboat and he’s told me about some things to watch out for. What kind of boat do you have?

Chris1956 · 2026-08-21T14:58:51-0600

I have a speedboat and a runabout. Both are outboard powered. I used to have a sunfish-style sailboat and have sailed with friends on charters.

I live on the bay, and could easily have a 35' sailboat, however, I lack the interest in sailing.

CamilleHarris · 2026-08-21T15:12:54-0600

Chris1956 said:
I have a speedboat and a runabout. Both are outboard powered. I used to have a sunfish-style sailboat and have sailed with friends on charters.

I live on the bay, and could easily have a 35' sailboat, however, I lack the interest in sailing.

Honestly I’m not learning to sail or buying a sailboat to go out on the open ocean. I’m mostly planning to use it on the rivers around DC or Maryland or maybe on a lake. Do you have a Facebook profile?

Advice on buying a sailboat.

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