The Working Man's Guide to Trailer Sailing

The Working Man's Guide to Trailer Sailing | Life of Sailing

Last Updated by

Capt Chris German

June 15, 2022

Let's face it, life would be better with a 40 foot sailing yacht sitting on the hook just off your front yard on a tropical island. But if you are not quite there yet, maybe you want to start a little smaller. Let me introduce you to the Trailer Sailer.

A trailerable sailboat is in many ways better than a keel boat or a dinghy. You can get a trailer down a boat ramp, it stores for free in your backyard, and it has many of the benefits of a keel boat or dinghy, with fewer drawbacks. Some might argue that the perfect sailboat is the trailer sailer.


Table of contents

Trailer Sailers offer the Best of Both Worlds

For the last five years I have dabbled in both trailerable boats and keel boats, and have personally owned two trailerable sailboats.

Sailboat on a Trailer

They really were the perfect boats for my needs. They were small enough that I could tow them with my Ford Ranger, but big enough that I could sail outside the demarcation line at Cape Lookout in North Carolina, just one mile from the Atlantic Ocean.

They had a water ballast system so I could sail my wife, two dogs, myself and a whole weekend's worth of gear and a 13 foot dinghy though the sand bars and shallows of Bogue Sound and never have to drop my center board once.

They also fed me by allowing me to teach a few dozen sailors to master the tempestuous winds of East Carolina before I decided Hurricanes-be-damned and moved to Utah, I must admit I choked up a bit because these boats owed me nothing and I was sorry to see them go.

Trailerable Sailboats Can’t Handle as Much

Trailer Sailers are not perfect for every occasion despite my enthusiasm. Oftentimes the wind was just too much for these little girls, especially in places like East Carolina.

On days like those, sailing was not possible and I would drop sails and just motor, awkwardly, up the channel home.

Anything over 15 knots and the boat would be overpowered and simply luff up into the wind while under sail.

Luckily I had a really good 9-horse yamaha on days like that and we still enjoyed a day on the water - mostly.

That is to say, we always had fun, except when we didn’t, and that was the case on 4th of July 2019.

Jennifer and I decided to head to the cape that weekend in our trailer sailer “Flo’s Revenge” to escape the holiday crowds that always seem to pack into Beaufort to celebrate a holiday in the pre-covid days.

We set out at 6 pm on Friday with a pile of food and beer, tents and charcoal, dogs and sleeping bags.

We sailed over with a reefed main and a motor and arrived shortly before sunset to find that our usual anchorage had been erased from existence earlier in the season by a storm.

We decided to find a new spot and selected one that wasn’t quite as protected with less beach and more exposure to the channel traffic.

The first night went fine and we arose the next morning to find a bright sunshiny hightide and a steady stream of boats making their way across from Harkers Island.

We enjoyed the day, although we discovered that our dinghy motor was on the fritz and that when the tide went out, we were hard aground tilting the wrong way. At some point in the night, a thunderstorm came through, that I managed to sleep through.

Unfortunately, the tilt of the boat made my wife roll out of her bunk and the hatch leaked perfectly onto her forehead. We were forced to close the hatch to keep the wind and rain out, but the little boat turned into a sauna with my wife, myself, and two dogs packed inside and a tropical East Carolina thunderstorm raging outside.

Our boat rode hard at anchor that night and bounced off the bottom as the wind pushed us up against the beach. By the next morning, my wife was ready to kill me for sleeping so soundly and the boat was a good 30 feet up the beach from the high tide line.

Our tent had been shredded by the winds and most of our food was washed out to sea or soaked in sand and saltwater. Needless to say, I was in deep trouble for sleeping so hard.

I waited for the high tide to come in and told my wife that we would head home as soon as we could float the boat. But as the tide came in, I realized that the storm had surged us higher than the morning tide would rise and I could feel my wife’s ire build to a level that I don't think I ever want to see again. She was hot, mosquito bitten, tired, wet and now because our boat was so great a beaching, stuck there until I could figure out how to get it off the beach.

Thankfully one of the parade of power boats came close enough that I could hail them and asked them to haul my boat off the beach, which they did with great difficulty. We sailed back home and put the boat in the backyard and never sailed it again.

I tell you this story because it illustrates the real experiences of trailer sailing, with all its drawbacks, but the truth is I did love that little boat.

Raise The Mast On Shore

Trailer sailers can be a challenge to launch and retrieve much like any boat, but with trailer sailers there is the question of the mast.

The mast on pretty much all trailer sailers can be raised and lowered on the ramp or at the dock, and that makes it way cheaper and easier than having the raise and lower the mast with yacht club crain or pay a yard to step your stick.

The challenge however is raising it on shore or in the water. I have done both and have decided it is way easier to do it on shore as you can reach all the fasteners and leverage the halyard from the ground.

And if your wife drops a turnbuckle, it doesn’t sink in 15 feet of water.

Watch Out For Obstructions

Dropping integral items in the water is just one draw back. I have also seen more than one vessel precipitously drop their mast immediately after stepping, by backing their trailer into a tree branch on their way down to the water.

It took them the better part of an afternoon to raise that mast and it came down in mere seconds when challenged by a scrub oak branch hanging over the ramp.

The worst part was, the entire boating world was watching when they struggled to raise their mast and when they dropped it at the boat ramp. Your best bet is to practice raising and lowering your mast in your backyard before ever trying to do it down at the dock or boat ramp and always look up for trees and wires.

Water Ballast

Another issue in launching was my water ballast. It was a blessing in shallow water for stability but proved a bit tedious when launching and retrieving.

My manual said to let the boat sit immediately after launching to allow the ballast tank to fill, but more than once I damn near capsized the boat when climbing aboard to check to see if it was filled.

Air embolisms could stop the filing process and without a full ballast tank that boat had the stability of a sippy cup on a glass topped coffee table.

Towing a Sailboat

Hauling was an issue as well. While my little ford ranger had no problem hauling the boat with a dry ballast tank, barnacles and seaweed could clog the ballast drain and make it a real challenge to haul.

I never had to dive under to dislodge any seafood samples, but I always was afraid I would have to some day, and had to wait until it was completely drained before trying to traverse the entire boat ramp when towing with my ranger.

My GMC however could haul that thing with flat tires dragging a danforth though so if you do decide to trailer sail, make sure you get yourself a decent truck to do your towing.

Other than the ballast and mast, launching and hauling is relatively similar to any other boat. Depending on how deep your draft is, a sailboat can be a bit more difficult on shallow ramps.

Lots of trailer sailer trailers come with extensions to allow you to drop the trailer even deeper into the water for shallow ramps and deeper draft vessels.

The big thing is to ensure that whatever trailer you use, that it works nicely with your hull. And most trailerable sailboats in my experience are a package deal with the trailer so I would recommend you go with the manufacturer when selecting a trailer and don't go shopping for a better deal on a trailer.

Maintenance Is Easier With a Trailer Sailer

While a trailerable sailboat is free of many of the pitfalls of boating like docking, yard fees and mast stepping, it is still a boat.

Engine troubles, bottom paint and on board storage are all challenges. No one that I know of has ever created a boat that doesn’t need oil changes, doesn’t grow barnacles and doesn’t need a ton more storage than it is designed with. It's just a boat.

With a trailer sailer, you can work on your motor next to your garage in your driveway and do all the fresh water flushes your garden hose can handle.

You can also skip bottom painting if you dry sail your boat, which is to say never leave it in the water for more than several hours.

But if you decide to leave it overnight, odds are you’ll have a scum line and barnacle babies by morning.

And for storage, the only saving grace is you can load your boat in your driveway and save the three dozen trips between your boat and the car at the boat ramp.

Register Your Trailer

You're also gonna have to register your trailer sailer and your trailer, if you decide to ever leave your driveway.

Septic System

You will have to ensure that you have a compliant septic system which is oftentimes a bucket or for the high brow sailors, a chemical toilet on trailer boats.

Most trailer sailers don't have a holding tank due to the fact that you don't want to have to drive down the road with a full holding tank. And many also lack a usable size water tank as well for the same reason.

USCG Boardings

Just because your boat lives in your driveway instead of on a dock, doesn’t mean it is not subject to USCG boardings when underway. So flares, noisemakers and PFDs are all legally required as well.

Other Trailerable Boats

We have a great article on the top types of trailerable sailboats. But there are literally all kinds both new and used.

One of my favorite is the corsair pulse, a boat being manufactured in Vietnam that is a trailerable catamaran.

Corsair Pulse Sailboat

I envisioned taking this boat up to the northern reaches of Canada and sailing in the Arctic with it.

It’s got enough room to live aboard with lots of winter gear. You can launch it virtually anywhere and it's stable enough that you probably won’t pitch-pole into sub freezing water.

Start Small and Cheap

But if a new boat isn’t in your budget, the used trailer sailer market is super hot right now.

With Covid 19, folks are looking for all sorts of ways to get away and not have to worry about exposure.

What better way is there to get away and socially distance than taking your trailer sailer to the lake or to a remote beach for the weekend?

You can pick up hunter 23.5’s for sale around the country with most offered for $6K or less. Hunter 27s are also to be found but go for $30K plus.

My suggestion is if you're gonna buy your first trailer sailer, start small and cheap. The bigger your boat the more expense and the bigger truck you’ll need to launch it.

Practice Parking With Your Trailer & Boat

No one likes to drive a trailer and even fewer people like to back one up.

Particularly when you have a sailboat with a 30 foot mast up. It's never fun and quite frankly embarrassing when you do it wrong.

I always tell my students looking to trailer a boat to go to a massive parking lot on New Year’s day and spend three hours practicing backing your trailer into parking spots. There really is no other way to get good at it.

Trailer Guides, Rollers, and Side Straps

Even if you can back your trailer beautifully, you also need to put your boat on your trailer and that is even harder when it’s a sailboat.

Installing trailer guides on your trailer if you don't have them makes a huge difference in lining up your boat with your trailer bunks.

I also like rollers instead of flat bunks to hold the boat on the trailer, but with sailboats that's tough because they can roll the boat off on the boat ramp prematurely when backing in.

My hunter has a bow bumper that never quite worked right on my trailer. The boat always hit too high or too low and the winch strap chaffed it.

I took to leaving the boat a foot back from the bunk and using a chain to hold the boat on the trailer.

Never take your boat on the road without side straps. Many people think that because there are trailer guides and a bow strap holding it on the trailer, that you will be fine.

But turning corners and sloshing water in the hull have a tendency to flip boats over while going home and no one wants to be the guy to pick his boat up off the highway or worse yet, have to flip your truck back over when your boat decides to take you for a ride.

Is Trailer Sailing for Everyone?

A resounding no is my answer to that whenever I am asked.

When I was selling my hunters, I had lots of tire kickers come by and more than a few who could never handle a little boat like this in what remained of their lives.

Age, obesity and gravity are all challenges when it comes to trailer sailing. On shore you have to climb up the trailer to step the mast and clean the boat and do all kinds of other stuff and in the water, you have an unstable deck with great big steps on to the foredeck and onto the dock.

As much as this boat was a plug and play sailboat, it wasn't for anyone who lacked a certain agility.

One time docking I got my foot caught in the life line with a student and came real close, if I didn’t actually fracture my wrist.

Trailer sailboats are smaller and less stable than their oversized cousins with the keels. If you are in anyway, limited in your physical prowess, a trailer sailboat may not be the best choice for you.

So that’s my take on trailer sailers.

A younger me would have loved to have a whole fleet of them, but as I age I tend to think a 60 foot catamaran far away from the North Atlantic is more my speed.

Trailer Sailers are way cheaper than keel boats to own without having to pay for a dock, mast stepping and storage, but they are not a plaything and should be respected like every other boat.

They meet all the requirements to be USCG regulated and they can go in big water if you want to take them there, but they are not an easy ride back.

Practice your mast stepping and trailer backing with no one watching and try not to be too much of a ramp hog while you're in the public eye.

Start small, as big boats are a pain to drive on a trailer.

So do good, have fun, and sail far. Thanks for reading.

The Working Man's Guide to Trailer Sailing
Capt Chris German

Capt Chris German

Capt Chris German is a life long sailor and licensed captain who has taught thousands to sail over the last 20 years. In 2007, he founded a US Sailing-based community sailing school in Bridgeport, CT for inner city youth and families. When Hurricane Sandy forced him to abandon those efforts, he moved to North Carolina where he set out to share this love for broadcasting and sailing with a growing web-based television audience through The Charted Life Television Network.

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