5 Things You Should Know Before Buying a Sailboat

Where You’re Planning to Sail

Where will your boating be taking you? This is perhaps the single most important factor to consider, before purchasing a sailboat, because in many ways it will inform all of the other important factors to consider. Sailing the Atlantic or Pacific is a completely different experience, exercise and challenge, to, say, Lake Michigan boating. A totally different vessel is required for boating in smaller rivers, so it would be somewhat of a waste acquiring a sailboat that’s purpose built for the open ocean.

Basically, the boat you settle on need befit the sailing environment.

What Sailing Experience Do You Have?

What is your boating experience level? Obviously by the time you’re considering going all in with a decision as big as buying a sailboat, you will have some sailing experience. It’s important to know exactly where you stand though, because sail boats aren’t built the same.

Some of the worst horror stories, stemming from a lack of sailing experience, involve enthusiastic sailors losing control of larger boats in an open water setting. The general rule, to ensure you’re on the safe side, is to start small. It’s quite the norm within the sailors’ circles to trade-up as and when the need to do so arises.

What’s Your REALISTIC Budget?

It’s just a fact of life in general, but definitely applies when it comes to owning, operating and maintaining an asset such as a sailboat, that being how there are many recurring expenses to have to deal with. Something like docking or storage fees are only “escaped” by a sailboat owner who perhaps also owns a waterfront property.

Mooring costs money as well, wherever it is that your sailing adventures take you, but then there are the numerous maintenance costs as well. So your REAL budget is a lot more than the listed price of acquiring the boat. In the world of boating, refit is inevitable and it does not come cheap!

New or Used?

This consideration will indicatively also be informed by factors such as your budget, but also by how long you plan to commit to the vessel you’ll be purchasing. A new purchase from Oyster Yachts perhaps always makes for a great option, because then you know that benchmark options allow you to sail anywhere and everywhere, in the ultimate style, comfort and luxury.

If it’s your first sailboat purchase, ideally you should be looking at a vessel that’s 22-27 ft in length. If you’re going with a used one, then one which is a decade to 30 years old will do. Fibreglass is your friend if you’re looking for low-maintenance and long-lasting quality.


So we’ve already actually touched on the size consideration, but that was from the point of view of a first-time buyer. Ultimately the size of your sailboat will be informed by exactly what your specific needs are. Chances are the space required will increase as you gain more sailing experience, but the size will also be informed by who you’re sailing with and how long you will be out on the water.

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