Buying a big sailboat means you are buying the need for paying docking/mooring fees. Really if you won't use it OFTEN, you are probably better off renting one when you need/want it. There are dozens of "permanently docked" sailboats at the local marina. Many haven't moved since I moved to the area in 1999. Those are definitively holes in the water demanding to be filled with money. Just sitting there, they require regular maintenance to prevent them from sinking. One local marina has several that the owners just gave up... Abandoned in place. Maintenance not kept up and they'd cost more than they are worth to make them able to be sailed again. One is for sale for essentially the cost to have it trailer-ed to your location for commencing rehab... You have to go look at the boat at least monthly (preferably weekly or more) to ensure it is not filling with water and sinking at the pier. Bilge pumps fail... You also need to keep an eye on the mooring lines. Join a yacht club that has boats you can rent. Get their training and certifications. If you don't end up renting the boat(s) often... you don't need to buy one. If you end up renting one every week for a year, it might pay off to buy. You'll have a better idea of what issues to look for yourself and what type boat you like to sail. A smaller boat is more convenient and can be stored under a "carport" in your back yard. Good for keeping the sailing skills sharp. If you won't take the small one out regularly, you won't take the larger one out either. "Buy small.. rent big" might be an option. Nope... I won't be buying a boat bigger than is convenient to tow for a day on the lake and then take it home in the evening.