Long time since I saw shoe eyelets as portholes! No reason why it shouldn't sail. Let's face it some of the best sailing any of us have had is with a Star yacht from the seafront kiosk when Dad was feeling generous. Let the sails out a bit on the bowsies and off it went to the other side of the pond. I had one for years! Eventually, Mum had to make new sails as the originals rotted, so an old bedsheet or one of Dad's shirts would be run through the old Singer, ready for the next years holidays.