Not myself, but I have seen Cpt. Jim Sharp dock the 122' schooner Adventure under sail, in through Camden harbor in the summer, he did that at least once a year, very inpressive.
I was wondering whether someone was going to mention seeing one of the maine windjammers docked under sail. When I worked aboard one, we watched the Heritage (94' on deck) do it. It also wasn't uncommon for the boats to sail into the raftups that we would have. Boy do vessel's with 100+ tons of displacement carry their way.
Personally, my largest was a 48' boat with a blown transmission. Certain points of sail, it isn't bad at all but others, no thanks.