Hunter 27
I have trailered and launched these puppies on many occasions. First, the trailer needs to be at least a two axle with brakes. Make sure the trailer is rated for the weight of the boat and trailer because if it isn't, you will blow tires. Long extension is a must. As for wash outs on the axle, this is nice if using in salt water. Launching is easier but plucking this baby out of the water is difficult unless you are experienced. Suggest a travel lift for pulling the boat out. As for the hull of the 27 and 26.5, I believe they are the same. raising and lowering the mast is a challenge too. I use to have 2-3 peole helping me and I would buttress the base of the mast to the mast step and would put it up. I do not recommend this at all. I would rig a mast raising system something simular to the Hunter water ballast boats. The big question is your mast step whether it is hinged or not. After all this, do you want to trailer a 27 and if so, leave a message and I will give you further inffo.
