When a leg of Stephen DiPietro’s winter travels got canceled, something told him to wait it out. He had been surfing in Portugal since Dec. 1. He and his pals were planning to fly into Morocco, but that government had shut down all travel into the country on account of the Omicron surge.

Meanwhile, DiPietro had forgotten that back in October, a California surfer, photographer and boater named Trevor Gordon had shared on Instagram he was planning to sail from Europe to the Caribbean and was…