Taking the Trailer on the Road Again

Sail News

Ghosting along off Florida’s Gulf Coast

It was early March and freezing cold in Michigan. Snow lay in patches on the barren fields, and dark clouds hung just above the treetops. Ice skimmed the roadside puddles as we left Ann Arbor, bound for sunny Florida.

I was driving a minivan and towing behind me a 16ft Wayfarer dinghy, owned by the Michigan Sailing Club. This was my first trailering experience. I’ve been a keelboat sailor for 50 years, but after I sold my Westsail 32, I’ve returned to my dinghy-sailing roots.

Trailer sailing has the enormous appeal of allowing one to explore new waters that are suddenly within a day’s reach by car, rather than weeks away by boat.

My friend Jeanne, a fellow member of the Michigan Sailing Club, followed behind keeping an eye on the boat and trailer as we headed south across Ohio—it was a great comfort to have her watching out for me.

Backing up the trailer in anticipation of another day of sailing

Backing up the trailer in anticipation of another day of sailing

Months earlier, another friend had kindly helped us replace the trailer’s wheel bearings. We’d managed it, but it’s also a job best left to a shop with the proper tools. Then, a month before departure, one of the fenders had broke off, taking a taillight with it. I was thankful this happened before we left, and not on the highway.

Although the Wayfarer and trailer weighed only 700lb, it was still a struggle getting over the Appalachian Mountains in Kentucky and Tennessee. I tried to stay at 65 mph, but on the steeper hills my speed inevitably decreased. Going uphill I kept the rpm at about 2,300, even though the cruise control wanted to rev it up a good deal higher. I didn’t see any need to overwork the engine.

The boat traveled well, although it would buffet and rock in the strong downdrafts from the big trucks that went by, and in the crosswinds coming off the cornfields of Ohio. The trailer had an extra-long tongue, which is great for keeping the rear tires of the tow vehicle out of saltwater when it comes time to launch, but also means an extra-long load.

Together, the minivan, extended tongue, boat and mast (which was hanging over the transom) measured about 43ft. That’s a lot of vehicle to have to keep an eye on threading your way through tight parking lots and down narrow streets. The longer tongue meant I had to be careful getting around tight corners, in particular.

When I pulled off for gas (every 200 miles or so) I also had to leave plenty of room before driving back out into traffic, which meant waiting for extra big gaps. Sometimes I had to wait before refueling, as well, because my “rig” took up the space of two gas pumps. My normal gas mileage declined by about a third towing both the Wayfarer and the small canoe I had on top. I usually get around 30 mpg, but pulling the boat with my 6 cylinder minivan I was getting about 19.

Trailer-sailing means hanging with the big boys at rest stops!

Trailer-sailing means hanging with the big boys at rest stops!

We followed the “1-10-100” rule, stopping to check the trailer and boat at one, 10 and 100 miles. It’s important to tie down all your spars and rigging before starting out, at the same time keep an eye out for any loose bits of gear. Even a light shroud can chafe through a boat’s gelcoat on a long road trip.

We also padded the mast and boom where they lay on the lazarette with foam pool noodles, and tied up the halyards and shrouds so they wouldn’t rub against the coaming. Finally, I tied the boat to the trailer using a series of trucker’s hitches, as opposed to using ratchet straps. The trucker’s hitch is fast, simple, uses no fiddly mechanical gadgetry and applies a tremendous amount of force to the tie-down line.

Early on I’d wondered why it was necessary to tie the boat to the trailer. Wouldn’t its own weight be enough to hold it down? Then came the time I lightly bounced over what I thought was a low curb only to see both the boat and trailer immediately become momentarily airborne. Ah! I thought to myself. Now I know why you always tie things down!

After two long days on the road, we arrived at our first stop, a campground in the Florida Panhandle, where we dropped the trailer off at the office because the campsite couldn’t accommodate a vehicle and trailer with a length of 35ft or more. It took only minutes to unhook the trailer, so this presented no problem.

The next day I found a nearby public launch site with the help of Google Maps, and we drove there under summery skies. The ramp itself opened onto a sheltered bay protected from the strong south wind that was blowing in at the time off the Gulf of Mexico making it an ideal place to go for a sail.

The author ready to set sail in the Sunshine State

The author ready to set sail in the Sunshine State

It was not until after I’d raised the mast that an alarmed local fisherman pointed out the overhead power line hanging no more than 20ft in front of the boat. Even though every sailor knows the danger posed by the combination of aluminum masts and power lines, I’d completely forgotten to make sure we were in the clear. I’d assumed no self-respecting boat launch would have power lines hanging overhead, but this was clearly not the case, especially in powerboat country. I’m accustomed to marinas designed to accommodate travel lifts hauling around sailboats with 60ft masts. Lesson learned—always be sure and look up! Not all boat launches have sailors in mind.

For a newbie trailer-sailor, backing a trailer down a steep ramp takes some practice. Personally, I found that looking over my shoulder was much easier than trying to use the van’s mirrors. On weekends, in particular, there will almost inevitably be other boaters around waiting in line, and brevity is appreciated. I was glad I’d practiced before the pressure of being “on stage” that first time. It’s easy to get flustered when others are watching.

Our first Florida winter sail was marvelous, made sweeter by the knowledge that back home they were enjoying another winter storm. That’s the beauty of trailer sailing—one day you’re dealing with ice and snow. Forty-eight hours later you’re sailing with dolphins, surrounded by palm trees.

All went well hauling out, even though I forgot to engage the bow winch ratchet, which caused the boat to begin to slip off the trailer the first time I drove up the ramp. There are lots of little details to keep in mind trailer sailing—I’m sure they’ll become second nature as I do more of this.

While we were unrigging the mast a sudden screeching, grinding noise startled us. Looking around we saw a powerboat trailer on a nearby street that had separated from its tow truck and was now skidded down the road attached only by its safety chains. A good reminder to always keep those chains attached!

The more I drove, the more accustomed I become to seeing the boat and trailer looming behind me, so much so I’m afraid one time I let my guard down. It happened one day after pulling into a drive-through to get my customary coffee. Making my way through the parking lot toward the road, I glanced back just in time to see the boat miss the building by mere inches. Note to self: Don’t forget to make wide turns and always stay focused. I sure would have hated to damage their building.

Pulled up on a beach a long way from the Michigan winter

Pulled up on a beach a long way from the Michigan winter

Another lesson learned had to do with the boat’s cover. I’d removed it when we left Michigan, afraid it would chafe to pieces over the course of such a long road trip, which meant the boat was now open to the elements. This was not a problem, until the time I pulled under the “protective” canopy of a pine tree one rainy night only to find the boat covered with a million needles the next morning. Won’t do that again!

When we left for Florida, I’d had grand visions of plopping the boat into numerous waters along the way, but then reality raised its thorny head. Finding a ramp, prepping the boat, raising the mast, rigging and finally launching was no small task. And, of course, you also have to not only go through the entire process in reverse but remember to tie everything down securely before driving away. It doesn’t take long before one begins to think twice about casual daysailing.

For this reason, we only went out for a couple of sails on our way down to meet friends waiting for us on Cedar Key, midway between Tampa and the Panhandle. Once there, we also decided to keep the boat in one place for the week, as opposed to continually picking up stakes. With the boat safely tied to a nearby dock, getting out on the water becomes a lot less daunting.

We spent our time there exploring the islands and reefs around Cedar Key, watching pelicans glide effortlessly above the sea, and listening to the quiet splash of water against the hull. White sand beaches lured us ashore, as we ghosted across still lagoons surrounded by dense stands of dark, green mangrove. It was heaven, made possible by the marvel of a small, trailerable sailboat. 


• Have a trailer shop check the wheel bearings every year—grease bearings frequently, especially if you’ve been in saltwater

• Small tires can’t go too fast—maximum trailering speed is 65 mph. Check wheel hubs for excessive heat at rest stops

• Unhook the trailer and turn it around by hand if you get into a tight spot

• Ramp conditions will vary from wet, to slippery, to steep to slippery and steep, so beware. Find a ramp that is protected from onshore winds and swell

• Pack some tools for small repair jobs: pliers, screwdrivers, saw, hammer, needle nose, socket wrenches, rigging knife, etc.

• Pack spares for the boat: extra lines, shackles, cotter rings, sail repair tape, fenders. As is the case on any other kind of cruise, you’re on your own

• Rig a mast raising line if the boat has a tabernacle. Run the main halyard to a small block tied to the trailer above the winch, then back to the cockpit

• Wash down the boat, trailer and sails thoroughly to clean them of salt and debris after use

• Check the trailer for loose or broken parts and verify that the lights are working. Check tie-town straps for chafe

• Bring plenty of short lengths of line for various tie-down uses

• Wheel chocks are handy. I left the trailer once on slanted pavement, and although I had a curb to rest against, I was glad I’d brought along chocks, just in case

• Practicing backing up, adding in some 90-degree turns, but don’t turn too hard and jackknife the trailer. This could damage the towing mechanism and even flip a light trailer

• Always wear a life jacket and hat, and use sunscreen. Just because you’re on a small boat doesn’t mean you don’t have to still be careful!

Ed Note: Charles Scott has worked as a freelance cameraman and photographer for more than 40 years. A world traveler and lifelong sailor, he’s logged 25,000 offshore miles on numerous ocean crossings. To see more of his work, go to seascottphotography.com

Photos by Charles Scott

June 2022

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