I have had Foremost insurance for several years but pretty sure it was the same with Dairyland and Progressive when I was with them. The trailer is covered as a 'optional equipment.' Most motorcycle policies offer a minimum amount of coverage ($3,500 by Foremost) and you can purchase additional for a price. But here is the rub: the maximum amount (with Foremost anyway) is $7,500 and this is for the Bushtec and all the goodies that have been added to the bike. My cost to increase the coverage to $7,500 is only $26 per year. For a stock bike, well maybe no problem. But for those of us who have added a lot to our bikes it is not sufficient. But then again the changes of having a total loss to both the bike and the trailer are small. Worst case is that both were stolen. Then the $7,500 would not be enough.