In the Winter,the best thing to do is put it in the heated Truck while trailering.Take out one piece at a time and put it on when you get to your destination.If ya' start yankin' and pullin' on cold enclosures,they are going to tear eventually. [Mike]
You have almost the same boat as me (Hydrasport 230 WA). I suggest putting it up, it is next to impossible to get it up when it is this cold. I trailer with it up and a snap or two come undone but it is ok. Like Skip said you will lose around 1 MPG.
Funny you should ask. I left mine on when I took the boat to the dealer in Grasonville. When I got over the bridge I looked in the rear view mirror and they were all flapping in the breeze. Luckly I only messed up two zippers and it cost me $50 to get it fixed.
I sympathize with you on putting on the curtains in the cold. It took me about 40 minutes to get them back on Saturday. I have heard of people keeping them in their truck and warm until they need them.
When I attended the power squadron boating course, thirty years ago, the course book, "Chapman's", "Seamanship, Piloting, and Small Boat Handling", unequivically stated that all canvas should be removed before vessel is transported on highway.
If you cannot get the curtains on when you get there, what good are they?
In summer, you will get bugs smashed on windscreen that will result in less clear windows when you clean them off.
In any season, but especially in cold weather, you will quicky destroy any curtain that comes loose when trailering. This damage may extend to other curtains or parts of boat from the battering.
I would make sure that curtains will not come loose. You may even screw them to boat at corners. Then I would drive at moderate speed and ,if I could not see the curtains in my rear mirror, I would stop and check them every so often.
A canvas shop can probably make you a window cover for bugs or you may cover them with cling wrap.
I think that the curtains will hold their shape and size better if they are left on all the time, but trailering is very hard on them.
There is no correct answer. Good luck.
If it's well made, trailer with it, if it's not dont. The Grady factory canvas only comes off the boat twice a year to treat the metal windshield frame. Almost 5 years and no trouble. Previous custom cover never came off with only minor repairs after 13 years. Buttons and zippers don't come undone either. Canvas is sure nice this time of year. Good luck, hope it works for ya.
I have the same boat -23 ft WA Striper and I have since got new curtains and they fit great. Although I do not own a trailer and leave my boat in a slip I can feel your pain. Have you ever seen those snap extenders? Most canvans places can make them for you and they sometimes sell them at west marine. If you had to take them off and couldn't stretch the curtains, try using the extenders until you get a warm day. I took my curtains off over the winter and it was a little tricky putting them back on in April for Spring season. The extenders work fine most of the time.