A new furling headsail awaits stitching at AirForce Sails. Most of this company's sails are built in China, but custom orders often take shape at its loft facility in Charleston, SC.

Buying new sails is a big step for most every boat owner. The joys of enhanced performance and greater reliability take some of the sting out of writing a big check to your sailmaker, but there's no getting around the fact that this is one of the biggest investments a boat owner will make. So the temptation to save a few bucks is strong, and we can certainly relate.

Because our empathy runs deep, we thought it would be instructive to assess the bargains available through online discount sail brokers—those that sell new sails and those that offer used ones as well. So, we logged on and set out to compare…