The “Star of India,” the oldest active sailing ship, sails into San Diego Harbor on the occasion of its 160th birthday. After a five-year activity pause, the ship set sail on a small ocean-going expedition, celebrated by the San Diego Maritime Museum.
Define active.
https://en.m.wikipedia.org/wiki/USS_Constitution
Old ironsides still has a yearly trip to turn around (so it weathers evenly), but that’s not really really active.
Wikipedia says that the Star of India has a crew of volunteers and sails at least once a year, typically returning the same day.
https://en.m.wikipedia.org/wiki/Star_of_India_(ship)
Unfortunately, it would seem the USS Constitution generally “sails” by being towed by tugboats.
This article from 2012 mentions that she had only sailed on her own twice in 130 years.
https://www.cnn.com/travel/article/massachusetts-uss-constitution/index.html
According to that article, they sailed unassisted for 17 minutes traveling 1100 yards. At that point she was re-attached to tugboats and towed back to dock.
Another article I read recently said that the crew for the USS Constitution is only about a quarter of what would be required to actually sail the ship.