Last June, as Americans began to emerge from lockdowns and into a new, uncertain stage of the pandemic, Amy Ryan and her family set sail in a 44-foot-long catamaran and headed up the Atlantic coast. They haven’t stopped sailing since.Ms. Ryan’s husband, Casey Ryan, 56, was on a partially paid leave from his job as an airline pilot, based out of Denver. School was remote for their daughters, now 7 and 11. Ms. Ryan, a real estate agent, could manage her team from anywhere. And they could rent out their house in Evergreen, Colo., on Airbnb. The family saw a window open, and they leapt through it.