OP:

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.

Get your boating license first. After that, try renting a boat for the summer or piecemeal. Try washing it, refueling it, doing an overnight to another city, etc. If you like it, you can buy one next summer. If you dislike it, or don’t think you’d do it as often as you thought, you saved yourself a lot of hassle.

I worked on boats a ton and got to know the ins and outs of maintaining them. Bit of a pain in the ass, but they are quite fun. Decent amount of hidden costs. It’s a fairly investing hobby, close to (but in some cases, not as expensive as flying a small plane as a hobby. You’ll spend a lot time working on the boat to keep it in shape for excursions.)

Cleaning motor boats is a lot easier than sailboats. And if it were me, I’d make sure it was able to be trailered, and look into how expensive fuel, maintenance, insurance and most importantly, slip fees and places you can moor your boat at other harbors. If you don’t wanna pay sticker, look at the used market. A lot of boat owners are sick of paying slip fees and might part with it for less money. The flipside is that they might take a ton of cleaning and maintenance to get back into shape.

One final tip: do not exceed your fuel range, and make sure there are multiple places to refuel if you are going camping in a remote location (eg, an island chain). Some fuel depots might not be operational or have limited hours on weekends or weekdays, unlike car gas stations. Our neighbors got stuck for a weekend out in the islands when the lone fuel depot was closed on weekends, and they didn’t have the range to make it to another island.

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

“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.

“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.

I posted this in the other thread, and it’s for the US, but ColRegs are international… https://www.navcen.uscg.gov/navigation-rules-amalgamated

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.

I recommend the Sailing Anarchy forums and nauticed.org if you think you’re into sailing!