So You Just Bought Your First Sailboat—Where Do You Begin?

Photo courtesy of Dianna Keen at These Days of Mine

You’ve fantasized about it, you’ve looked, you’ve shopped around. You crawled in, under, and around a bunch of sailboats that other people wanted to get rid of. Finally, one grabbed your imagination more than any other. In your mind’s eye, you could see yourself as its proud owner and in command of its sails and rudder. You made the decision and you brought it home.

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Now, what? Your fantasy of cutting through waves with the wind in your face is still off in the distance. Unless you bought a truly ready-to-sail boat, you now have a project. You might know SOME of the work that needs to be done to make your new-to-you sailboat seaworthy but do you know ALL of the work? What’s the most important? What can wait? You don’t want to spend all of your foreseeable future working on your boat and not sailing it. That’s not what you signed up for.

Following is a checklist that you can use to get your new sailboat ready for a season of fun dancing on the water. Each item on the list points to articles from the archives that will give you the details and the guidance you need to check it off the list. This list is prioritized, starting with the most important items first. That is, safety, which should always come first. Then it progresses through the necessities until all that remains are the conveniences. Those you can take care of later as time allows.

Safety Gear

Your crew’s safety should be your number one concern. Boating accidents are very common and although accidents involving sailboats are not as common as with powerboats, any is too many especially if it involves your sailboat.

To be prepared for the worst, carry the greater of your state’s mandated safety equipment or the US Coast Guard required safety equipment onboard at all times.

That typically includes:

photo4Be sure your crew knows where all the safety equipment is located and how to use it. That means you practice man overboard recovery procedures with each crew member. But that’s just the minimum. Depending on the kind of sailing you do, it might be wise to invest in additional safety equipment like:

Trailer Safety

The fun can’t begin until you get your refurbished pocket yacht to the water safely, whether it’s just to launch it and then tie it up in a slip or whether you’ll tow it to every cruise and become a trailer sailor. Boat trailers get a lot of neglect and abuse–neglect from sitting for weeks or months out in the weather or abuse from regular dunking in water without proper maintenance.

Even if your sailboat came with a decent a trailer that was maintained well, it might not be ready to hook up and go sailing just yet. The sailboat on its trailer is only one-half of the complete towing equation. The other half is your tow vehicle. Be sure that the vehicle you intend to tow with can handle the load. Read the door post stickers or owner’s manual to find the vehicle’s maximum towing capacity and don’t exceed it. That includes the trailer, sailboat, outboard motor, and everything you put onto or into them.

Right wheel. Extra tubing is rolled into a coil.

Your vehicle’s towing capacity is primarily the frame and suspension’s ability to support the load, the cooling system’s ability to prevent overheating, the drivetrain’s ability to move it up hills and down the road, and the braking system’s (nominal) ability to bring it all to a safe stop. It doesn’t necessarily mean that it can also stop that much of a load in traffic or on a crowded highway.

Most state laws specify the minimum weight or a percentage of the towing vehicle weight at which a trailer is required to have its own braking system. Check your state and local towing regulations and if you’re even close to the limit, install Do it Yourself Trailer Surge Brakes anyway. They’re inexpensive insurance when you consider what could possibly happen and your potential liability if you were to rear-end another vehicle with an excessive load. Plus, they make trailering much more relaxing, especially if you have one of today’s smaller SUVs for a tow vehicle.

Also, check that the trailer bearings are properly adjusted and greased. Bearing Buddies make lubrication simple and ensure that the hubs are under constant pressure to keep water out.

Check the tires for age, load rating, and air pressure. Trailer tires typically time out before they wear out. That is, your state may have regulations as to the maximum age of tires that are allowed on state highways. Older tires can become hard, crack, and fail unexpectedly, especially at highway speeds. Not all tires are created equal. Most passenger car tires are underrated for the loads carried by most trailers and shouldn’t be used. Always keep the tire pressure at its maximum to avoid overheating and poor handling.

Lastly, ensure the trailer coupler and hitch ball are the same sizes, that all lights work correctly, and learn How to Secure Your Outboard Motor for Safe Trailering.

Keel Condition

Your sailboat’s keel is what keeps the boat upright. Its condition is not a major concern for fixed keel and wing keel designs, but swing keels have been known to detach accidentally. More common is that the winch cable breaks or they collide with an underwater object or ground, retract partially, and then after clearing the obstruction, free-swing and collide with the keel trunk, sometimes causing enough damage to take on water.


Your swing keel is a system of interrelated parts that, if any one of them fails, can lead to expensive and sometimes dangerous damage. You can safeguard your swing keel system by learning the Five Swing Keel Maintenance Blunders and How to Prevent Them.

If your swing keel is badly corroded and in need of refinishing, you will find complete instructions in my five-part series that begins with Refinish Your Swing Keel for Best Performance, Part 1: Removing.

Standing Rigging

It’s the standing rigging that keeps the mast, well, standing. Think of the mast like a giant lever and the sails as hands that push on that lever. The standing rigging has to transfer all that force to the hull of the sailboat or else the mast will bend or break. Some of the force drives the sailboat forward and some of the force pushes (heels) the sailboat over in the water.

Standing Rigging

Most sloop-rigged sailboats are equipped with:

  • Forestay—supports the leading edge of the foresail and holds the masthead forward.
  • Upper shrouds—hold the masthead centered athwartships (side-to-side).
  • Lower shrouds—hold the middle of the mast centered athwartships and fore and aft. It’s also used to give the mast a slight prebend to improve mainsail shape.
  • Backstay—holds the masthead aftward. Also used to adjust mast prebend and adjust forestay tension.

Depending on the age of your sailboat, how it’s been used or abused, and how it was maintained, you might need to replace the standing rigging. Broken wires and corrosion are the tell-tale signs of expired wire rope. For more information about evaluating or replacing standing rigging, see How to Replace Your Standing Rigging for Less.  Get the same info plus popular standing rigging upgrades and running rigging upgrades in my eBook Do-It-Yourself Small Sailboat Rigging.

The running rigging (ropes) is less critical and breakage usually isn’t catastrophic. But if you want to replace your running rigging or you want to lead the lines aft to the cockpit, see Lead All Lines to the Cockpit for Safer Sailing.

Motor Condition

Sailing is about harnessing the power of the wind. But make no mistake, you WILL need a reliable motor at times, especially while you’re learning how to handle:


  • Launching and retrieving with a trailer
  • Entering and leaving marinas, slips, and docks
  • Raising and lowering sails
  • Anchoring
  • Lulls and windless periods
  • Lees of land features
  • Emergency situations

Whether your sailboat has an outboard or an inboard motor, you should go over it from top to bottom and maintain it in excellent working order. To help you get started, I wrote 15 Outboard Motor Maintenance Blind Spots You Can’t Afford to Miss. Become a master mechanic of your motor.

Staying Afloat

It’s common for older sailboats to have a little water in their bilges but that doesn’t mean it’s acceptable. Your goal should be a clean, bone-dry bilge. Water inside a boat promotes mildew, mold, and corrosion. Be ruthless about detecting and stopping every leak as well as moisture condensation.


Be particularly wary of any openings in the hull or plumbing below the waterline. Through-hull drain fittings, cockpit drains, keel winch cable tubes, speed and depth transponders, and the like can fail and sink a sailboat in minutes.

Don’t let your sailboat be vulnerable, especially if you will leave it unattended in a slip for any length time. An automatic bilge pump is a worthy precaution but even they fail so don’t rely on one.

For starters,  Clean That Filthy Bilge! Then if your sailboat has a swing keel, also read Five Swing Keel Maintenance Blunders and How to Prevent Them. Take the next steps by reading Replace Old Drain Tubing and The Complete Beginner’s Guide to Ball Valve Maintenance.

Required Lighting

Anchoring overnight in a secluded cove can be one of the most rewarding experiences you have when sailing. Cruising by moonlight is another treat and a worthwhile skill to learn even if you only prepare for an emergency. These situations require proper running and/or anchoring lights. Start by knowing which lights are required for the length of your sailboat in various situations by reading Rule 25 of the US Coast Guard Navigation Rules. To become an even better skipper, study the entire document, particularly Part B – Steering and Sailing Rules. These are also in the free Boater’s Guide to the Federal Requirements for Recreational Boats published by the US Coast Guard.

LED conversion

Once you know what lights you need, check your sailboat’s lights to confirm that they work properly. If they don’t, repair them before you operate your sailboat in darkness. If the electrical system is beyond repair, How to Completely Rewire Your Sailboat will guide you through upgrading the entire system.

If your sailboat doesn’t already have an anchor light, check out How to Add an Anchor Light For Less. When you have working lights, you can improve their efficiency, reliability, and brightness with Convert Your Lights to LED Bulbs for More Light with Less Power. For more convenience and enjoyment, you can also Add a Solar-Powered Flood Light in Your Cockpit and Brighten up Your Cabin with LED Strip Lighting.

You won’t need an expensive, clumsy, and unreliable solar panel to charge your battery if you Upgrade Your Outboard Motor to Charge Your Battery.

Mast Stepping

So you’ve got your sailboat and trailer in ship shape again and you got it to the water safely. Now comes the single scariest thing that a new skipper of a trailerable sailboat has to learn, to step and unstep the mast. And you would do well to be nervous about it. Stuff happens. I’ve read numerous stories of mast raisings gone bad in which the skipper wound up looking for a replacement mast because his was bent like a hairpin.

But don’t let that scare you away from learning to step your mast or from trailer sailing. If you take your time, have a helper for at least the first couple raisings and lowerings, and keep an eye on all the moving parts, you should do fine. These sailboats wouldn’t have become so popular if ordinary people couldn’t step the masts themselves.

Mast Stepping with Boom Gin Pole

There are lots of resources online that show different methods for stepping the mast, everything from brute strength to factory gin pole systems, to elaborate A frame contraptions. Your needs will probably fall somewhere in the middle.

Two healthy people can step an average mast under normal conditions without extra gear. If you’ll be single-handing your sailboat, have physical limitations, or you just want to make the process easier and safer, then see my article How to Step a Mast Single-Handed With or Without Using the Boom as a Gin Pole. It contains links to five videos that I produced that show you the method that I use to raise my mast by myself with complete control. It also shows my DIY mast stepper that you can get the drawing of to make for yourself by subscribing to this blog.

Whatever method you choose, practice it before you get to the water’s edge and until you’re comfortable doing it. You might find that it helps to have a checklist to help you remember all the setup steps and their correct order to get your sailboat launched. I made such a checklist to help you get started. You can download it from the Downloads page if you’re a subscriber and customize the checklist to fit your own needs.

Do Your Homework

You can launch your sailboat, point it to the horizon, and learn to sail by trial and error. Or you can study a little in advance and save yourself a lot of headaches. You’ll still make mistakes and learn from them but hopefully, they’ll be smaller mistakes and you’ll spend more time having fun.


Get familiar with the basic principles of sailing with books like Royce’s Sailing Illustrated Volume 1Plain Sailing: Learning to See Like a Sailor, and The Annapolis Book of Seamanship. Then try and practice what you’ve learned out on the water. If there is a sailing school near you and you can afford it, take a class or two. There’s no faster way to jump up the learning curve and you’ll probably make some sailing friends in the process.

Also, get a navigational chart of the area that you plan to cruise in. Study the contour lines for shallow areas, highlight hazards, note the positions and distances between landmarks, identify the navigational aids, and find interesting places to explore.

Then get out there and make your fantasy into your reality!

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3 Comments Add yours

  1. Diego says:

    Ken, another great topic! After completing my own 3-year restoration project, I would also add a healthy dose of “determination” and “perseverence” to the mix. There were numerous times my project would have “stalled-out” without those two ingredients.

    1. Very true, Diego.

      This post only suggests some of the most important projects to start with, it doesn’t even touch on the mental power tools it takes to complete an extensive refit. Not everyone has the self-discipline to stay motivated, creative, and patient. Even if we do, our spouse may not. It can cause a lot of friction if not managed well. It reminds me of building or remodeling a house. But as I’m sure you’ve discovered, the end result is worth the work when we can make exceptional memories together doing fun things in fun places that we would never have imagined before.

  2. Jen says:

    Great read! I am in my second month of boat ownership, some of the points were not applicable to my particular vessel. Full keel, not swing, with a keel stepped mast. I also have running backstays.

    Planning to pull my boat out of the water and work on her over the winter. Check all the through hulls and valves. Install some new valves and a manual bilge pump, maybe even a bilge alarm. Engine, engine, engine… yup thats a job for sure. Even though my boat has a little engine room the wires are a disaster running everywhere and zap strapped all over the place. Dirty, hard to tell if there are coolant, oil or diesel leaks! If there were its too dirty to know.

    Lots of cosmetic things to be done but its a good reminder that yea, safety stuff first as the time and money will run out before the things to do will.

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