Although some sailors choose to just charter periodically or join a sailing club, most aspire to eventually have a sailboat of their own.
With your own sailboat, you can go sailing whenever you want, you can set it up to suit your own needs and preferences, and you can leave all your personal gear on board so it’s easy to pop down to the marina after work and head out for a sunset sail or for a weekend at your favorite anchorage.
When to Buy Your First Sailboat
So much of sailing is about the feel of the boat and the wind that you really need to just get out on the water as much as possible and sail.
As soon as you have learned enough to:
- get to and from the dock,
- understand who has right of way on the water,
- get back to a crew overboard,
- and have reasonable confidence in sailing a boat from point A to point B,
it’s time to get regular access to a sailboat so that you can practice, practice, practice (oh, and have fun, fun, fun, too).
Your First Boat vs Your Forever Boat
Many people have a goal in mind when they learn to sail. It might be sailing amongst the local islands for two weeks with the family or it might be sailing around the world. The right boat for these goals is often in the 30-45′ range.
The natural inclination is to go buy the “forever boat” that will meet these dreams. This is usually a mistake.
Your first boat should either be a small sailing dinghy if you’re willing to get wet (what better way to remember what not to do than to end up in the water?) or a 22-28′ “keelboat” (a sailboat with a heavy keel that keeps it upright).
Why buy a smaller first boat that you know you’ll need to upgrade later?
Learning: The smaller the sailboat, the more immediate the feedback. It takes a long time for your inputs to have an effect on a 16,000 lb 35′ sailboat compared to a 4000 lb 26′ sailboat. To learn quickly, you need that instant feedback. This is why many of the best sailors started by sailing dinghies.
Safety: The forces on the lines of a smaller sailboat are such that you need minimal mechanical advantage and you are less likely to get injured when you make a mistake. This includes manhandling the boat around the dock as you learn the sometimes challenging art of docking.
Cost: The cost to buy, dock, and maintain a boat goes up roughly by the cube of its length. A 40′ sailboat costs about 3.5 times more to own than a 26′ boat. If all your going to be doing in the first couple of seasons is sailing around the bay and to nearby anchorages, why be paying for a boat that’s designed for crossing oceans?
The Right Fit: This is by far the most important point. At the beginning of your sailing career, you just don’t know enough to really know what “Forever Boat” will be right for you. This is especially important if you plan to do any longer-term voyaging. Your boat will be your transportation and also your home while you’re on it.
There are thousands of unique boats on the market and owners and brokers who are eager to sell them to you. Unless you have some experience, you really don’t know what you’re looking at and you don’t know how it will handle under sail in different conditions, what the maintenance burden will likely be, and even what it will be like to live on for a week or more.
How can you evaluate an anchoring set-up if you’ve only anchored a couple of times during a course? How can you really understand the implications of access to the engine if you’ve never done any engine maintenance on a boat?
Sailors love to endlessly debate the virtues of catamaran vs monohull, full vs fin keel, cored vs solid hull and deck, ketch or cutter vs sloop rigs, the list goes on and on. Only with experience and research will you develop an idea of what all of these terms even mean and what is important to you.
There are no right answers. Different boats are right for different people and different missions. Give yourself some time to learn to sail and learn what will work for you before you take the leap.
Ironically, larger sailboats aren’t very “liquid” assets. They take time to sell, sometimes a year or two. Buying a large sailboat on a whim and then deciding it isn’t right for you can take longer to correct than buying a small boat for a couple of years of sailing while you look around, talk to sailors, and find the right larger boat for the long haul.
I met a new sailor last year who’d made a horrible mistake. He just didn’t know it yet.
His first sailboat was a 46′, 40 year old, full keel ketch in poor condition. He’d paid way too much for a boat that was way too difficult for him to handle on his own. He couldn’t find anywhere to moor it locally and had no budget left over for maintenance. He was relying on friends to come and help him sail it, but friends get busy (especially when there’s maintenance to do).
The Right First Sailboat
The perfect first sailboat will be affordable to buy and own, large enough for an overnight or a week away, and easy to sell in a couple of years if you want to upgrade.
The exact manufacturer doesn’t really matter, but I would recommend buying something that’s fairly common in your neighborhood. This will make it easier to find parts and advice and easier to sell in the future. This point is by no means crucial, though.
The perfect first sailboat is:
22-27′ long: This is right in the sweet spot for size. My first was 26′ long.
10-30 years old: Any younger and you will see a lot of depreciation when you sell it. Too much older and you may have extra maintenance issues (though this really depends on the boat). My first was 40 years old and the deck was starting to go.
Fiberglass: Fiberglass lasts forever and needs little maintenance.
Sloop rigged: This means that there is a single foresail and a main. This is both the simplest and most efficient rig. There’s no reason for anything else on a boat this size.
Fin keeled: There are those who believe a full keel (which goes the full length of the boat) is better in very heavy weather, but you’ll be avoiding these conditions and a fin keel boat will perform much better and be much, much easier to maneuver during docking.
In Good Condition: No project boats! The point here is to get out on the water and sail your butt off. Make sure that it’s a boat that you can sail away today, even if it does need some work (all boats need work all the time. It’s called “the list”).
A Note on Trailer-Sailors
Trailer sailors can be great boats. You don’t need to pay marina fees and you can take them “at 60 mph to windward” to new cruising grounds.
However, you need to be confident that you’ll take them out sailing frequently. If the mast is difficult to put up and take down, you’ll start to find reasons not to go. Carefully evaluate the ease of rigging and your own willingness to fiddle with it daily.
Some places have dry storage yards next to a boat ramp so that you can store the boat on its trailer with the mast still up. This is a great compromise.
So start scouring the local classified ads. It’s time to find your first sailboat!