These are early pictures of the trailer before the keel guide on rails were added. The trailer is a 2999 pound class trailer which means that in California, it legally doesn't need brakes. The towing capacity of my Mercury Villager minivan is rated to tow that trailer class but recommends trailer brakes for loads over 1500 pounds. I had to step up one size in trailers in order to carry brakes. The brakes system is actuated by the Carlisle Hydrastar system. A Tekonsa controller in the car sends a deceleration signal to the Hydrastar. The trailer has Kodiak hydraulic disk brakes.
The galvanized trailer was custom fabricated for the Vagabond. In order to get the boat and trailer into the garage, the whole trailer is built as low to the ground as feasible. The tongue and mast crutch are removable. As separate extendible launch bar pulls out just to the right of center to minimize how much of the van dips into the salt water.
The last picture shows the boat loaded on the trailer. She sits down low behind the van which I think tends to minimize frontal area and thus wind resistance. We have towed the boat about 6000 miles now. The fuel mileage drops from 20 to 16 MPG. We have towed up some 6 percent grades and have always made it to the top. On the flat freeway, we can drive faster than the 55 mph California trailer speed limit. I have driven the rig with the brakes disconnected and with care, can control the boat and trailer but the brakes are comforting. I expect that the boat, trailer and cruising gear come pretty close to the load limit. We try to add gas, water and some provisions just before we launch.
I started out thinking I could use a 2500 pound trailer without brakes and expected the price to be about $1500. With all the bells, whistles and retrofits, the price of the trailer is nearly three times that.
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This will be a couple of pictures relating to how I raise the mast and get the boat in the water for now. We hope to develop a check list to make a procedure out of rigging the boat and hopefully reduce the time. I am working on more permanent fixtures.
The first picture shows the two part crutch. The mast is supported during transport by the lower notch on the aft crutch, a temporary crutch that fits in the mast tabernacle, and the trailer mast crutch. The upper part of the aft crutch bolts on before we raise the mast. I use the spinnaker pole attached to the track fitting at the base of the mast as a gin pole. I temporarily attach two side stays to steady the mast. The fittings are shown in the two pictures below. We have used the system to raise the mast both in the parking lot and out on the water at a dock. I use the genoa halyard and the 4 part mainsheet tackle with the gin pole.
Notice the boarding ladder on the starboard side. This is a standard Windline collapsible ladder. It folds up on top of the skirt. It is very handy for boarding the boat both on the trailer or from the water.

I learned a few things from trailering experiences, most of them bad. You'll have to wait for these stories.