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

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.”

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.

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.

“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.

“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.

I’m in California and did the American Sailing Association ASA courses. First one ASA 101 is a weekend and was like $300 teen years ago. You need to read the book and it’s 100 question test then the weekend is for hands on sailing. That gets you inland waterways, bays, lakes etc up to 27 ft. Then rent from local club on those sized boats. I joined a sailing club for a few hundred a year and get discounts. Them take your ASA 103 coastal cruising & 104 bareboat courses which were like 700 combined. then you are bare boat certified and can rent up to 50 feet. Rent up to that size for a while then buy. There’s additional courses for further developing your skills. I went on to do the catamaran 114 and the pure navigation 105. Then did some endorsement courses for customs/international and night time. I’ve charted boats in Mexico, SE Asia, and Greece as captain with my friends. Great trips. Especially if you are also scuba certified. I bring my gear and do dives in the trips. If not in US, look up your sailing association. The British one is most respected worldwide I hear.

OP:

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.

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

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.

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

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