Any of you BSDs own a sailboat? Thinking of getting one for next year and would love to hear some cautionary tales about how they’re nothing but a money pit.

Looking to get a 25 ft catalina under 10k primarily to use in the long island sound.

Boats and swimming pools are wonderful things for your next door neighbor to own.

In Minnesota we refer to this as the “Friends with cabins” phenomenon. A cabin/lake home is wonderful, especially when you get to show up on Friday, leave on Sunday and put in 0 hours of work in between.

My in laws have a boat, and like most boats, it just sits in the garage. I think getting a boat is like buying OTM calls. Maybe there is that one time when it will be worth it, but otherwise it just decays. Like maybe that one incident when you are with some girl in the ocean and she cannot escape. Other than that though…

Also, given numi’s recommendation, perhaps you should consider motorboat also.

Second and best day of your life etc.


i.e. the implication

The 2 best days of your life is the day you buy the boat and the day you sell the boat.

BOAT - B reak O ff A nother T housand

Where are the customers’ boats??

Sold my sailboats (2) years ago after 20 years of life affirming and amazing experiences…was a beautiful O’Day 27’ sailboat that I kept at Spite Island YC off Norwalk-Westport CT. Sold only because the wife was less interested in cruising the amazing Long Island sound destinations and my heavy travel was interfering with my enjoyment.

It all depends on your inner yearning - some people buy it for the wrong reasons and sell it within 2 years - can’t be an impulse buy but something you have been thinking about and you must feel the pull of the freedom and adventure and beauty and commeraderie sailing can bring. Your expectations sound reasonable and that size boat will serve you well in LI sound from City Island to the reaches of Block Island.

In addition to the up front cost it will cost a few grand per annum to store it, dock it, maintain it, insure it, gas it. Can never justify it on a cost per sail basis but then again I’ve had a priceless run with my boat.

Will probaby downsize to a flying scott day sailor/racer to stay in the game once I get off the road…as you get older it just gets harder to round up folks for a sail and my club has a well developed racing fraternity thats lots of fun!

Good luck with your decision…

That’s it?!

He forgot depreciation… which is like millions of dollars

boats are huge money pits.

I don’t see the appeal. If anything i’d have a speedboat.

A boat is like a country club membership. You can never justify the cost when you sit down with your calculator and conduct a NPV analysis, but if you use it often and you have a true passion for sailing/boating or in the case of a country club membership golf or tennis, it can be a justifiable/worthwhile use of discretionary income.

Yes very true thommo77, and many people on the outside looking in would not appreciate that!


In my experience, people with CC memberships/boats/luxury cars etc. fall into two camps.

1 - They’re wealthy, and can legitimately afford them, and don’t mind paying for the convenience.

2 - They’re faking the funk, can’t afford it, but want others to think they’re successful, wealthy people.

Either way, there’s no point in telling them not to get it.

Good point.

Some funny remarks; I guess of all the reasons to own a boat I guess just wanting to enjoy one is not a consideration. Greenman I suggest you have had a very limited experience.

I also learned that I had omitted depreciation from my annual expense…since the “up front” investment had already been defined ($10K) I was including only cash outlays during the life of the boat as would most knowledgable folks that evaluate an “investment” based on cash flows. I thought this was an investment community lol?! Depending on the size and type of boat, where you keep it in season and off season, and many other factors dictate the cost but for a sailboat that size that is a reasonable starting point unless you plan on keeping it at the South Street Seaport

So LBriscoe follow your heart and head everyone has an opinion some are not worth a grain of salt

I’m sure Greenman’s mentality is not that we should not do things that we enjoy. However, people are free to choose the activities that they become invested in. I could choose to make a hobby out of skiing, which is expensive, or running marathons, which is cheap. It would be difficult to argue for an innate human preference of one of these activities over the other. So, from the perspective of Greenman, who deals with many wealthy and often superficial clients in his tax practice, it is likely that other factors influence the choice of activity.

If you own it directly (and not through a company), depreciation is irrelevant since it’s not tax deductible. Only the ending cash flow when you sell it is.