Weather Bird is more than a classic, wooden boat. The 101-foot staysail schooner is a whispering storybook from the 1930s when luminaries like Ernest Hemingway and Cole Porter rubbed shoulders out at sea. Coco Chanel walked her teak decks. Pablo Picasso found inspiration amid the rich varnished woodwork. Louis Armstrong reportedly wrote a song about the yacht and then hid the record deep inside the frames of the wooden hull.

The 90-year-old boat wears her age well, having emerged from a 12-month refit last year with a complete mechanical overhaul. Weather Bird’s current owner bought the yacht 18 months ago. His two previous boats were Tecnomar motoryachts—an 83-footer and a 120-footer, which caught fire in Mykonos. But wooden schooners are his passion, and though the vintage collector has experience renovating classic cars, Weather Bird was his first antique yacht.

For the Greek owner, the experience has been less restoration, more in-depth reconditioning. The Vladimir Orloff-designed oak hull is original, but virtually all else, such as fabrics, lights (made from opaline rather than glass, as per the 1930s) and interior cabinetry are new, albeit in sympathetic Art Deco style. The owner commissioned an artist to create sketches of what Weather Bird…