Lulu Belle, The Freewinds at Flag evolution is usually every year in October, for 30 days, while the ship is having it's bottom scraped and repainted.
From things I've read, the Freewinds has been in drydock for much longer periods of time in the last five years or so than 30 days a year. More like months.
What about when GAT came out and all the OTs had to retread? From what I recall, there were no OT VIIIs being made at that time. I don't think the ship was floating around much then.