As my accountant once told me: if it floats, flies, or fucks, lease it.

The best two days of owning a boat is the day you buy it and the day you sell it.

“Sailing is like standing in a cold shower ripping up $100 bills.”

I had a sailboat for a bit when I lived in Vegas. I absolutely loved sailing. I had a relatively small, cheap boat which was fine for lake mead. It was still expensive though. Everything continuously breaks on a boat.

If I hadnt gotten my dream job in Colorado I would have wanted to live near the ocean and own a sailboat.

Start with getting some experience before considering buying a boat. Not only can you lose your investment, but your life. Job a club, take lessons, make friends at the local yacht club, volunteer as crew. Requirements for being a skipper vary quite a bit between countries. Some let anyone go up to a certain size, others require certifications even for small dinghies.

The bigger the boat, the harder it is too both manoeuvre and maintain.

Do you want something small that you can roll into the water on a ramp when you use it?

Do you want something big enough that requires a crane to get in the water? Prepare to spend a week cleaning, sanding, polishing, waxing and applying new anti-foul yearly.

An ocean going boat isn’t for a beginner. I’d stick to a car. :)

A sailing boat is tricky to manage solo, if you’re on your own, I’d steer clear.

I once was super dead set on sailing the Carribean. Planned for two years and finally bought a 34footer. Sold it within the same year. And I am still trying to dig myself out of that financial hole. I much prefer my RV.

IMO: look into “boat sharing”. Unless you have a lot of $$ and/or lots of experience with boat maintenance… You do not want to own a boat.

Old cliché is (it’s true): “It’s better to have a friend with a boat.”

One important thing to know about sailing boats is that sailing is a skill and you need to learn a lot to be able to use the boat. Motorboats are way easier to use.

I like sailing so I prefer a sailing boat, but if you just wanna go on trips and don’t care about the sailing then you need to be prepared to learn and practice a lot

“The best 2 says in a boat owners life is when they buy it, and when they sell it”.

Start with renting & work to get your captains license.

Growing up on a very large lake I have plenty of horror stories about people who don’t take boat safety seriously, drunk driving etc. It is easy to pick up but the possibility of you fucking up your life (and others) increases.

For cheap and easy sailing, try Hobie Cats, small catamarans that are a blast to sail, very easy to learn and navigate with.

Be safe. Water turns a minor issue into a potentially deadly one.

Boat owner here and grew up boating. Mine and my husband’s happiest place is being on the water on our boat. BUT it is expensive and there are a lot of considerations and you very much need to know how to properly operate one and know the rules of the water. For example, docking is a skill in many conditions, it’s way harder than it looks, make sure you understand right of way, constant bearing decreasing range (if a boat looks like it is in the same spot relative to your position but it keeps getting bigger and bigger you’re on a collision course), know how channel markers work (red right returning), know how to read marine maps and understand tides and how much water your boat draws so you never run aground, where are you going to keep your boat-dry slip/wet slip/boat house storage and if it’s dry storage you need a trailer for the boat and a car (truck) that can pull the weight of the boat and the trailer, then you need to learn how to launch a boat (this is just comical to watch people try, me included, I don’t even try). Dock space is expensive, fuel is expensive, maintenance is expensive. Buy used but ask how many hours the boat and engine have on it, don’t just rely on the age. And ask about maintenance history. Know that engines are WAY more expensive than you would think. And please please please take a boat safety course and get your license. If there’s any way you can be on and around other people’s boats and just watch and ask questions for a while I would highly recommend that! Two biggest things- pay attention to the weather and always put the plug in before you launch the boat!!

God speed friend

OP:

The only thing I know about buying a boat is that it’s the happiest day off your life, followed by selling your boat.

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Not a boat owner, but trained on sailboats: if you feel like it, take sailing lessons and get a feel for it, it’s fun and relaxing. I hate motorboats for the noise, the environmental impact. And it’s kinda dull.

In any case, navigation and boating in general has rules, depending on where you are you may have to get a license.

Got to your local sail club, take lessons. When you’re trained you will be able to rent boats from time to time. Almost nobody sails enough that buying is reasonable. And anchoring in a proper port means an annual fee to pay.