We were in Red Hook & Cruz Bay a couple of years ago before I was sailing. There were multiple signs on stakes by the sand / docks & flyers in the Marina offering day sails
for $60 - $90 per day, depending on food or beverages provided & more to go to Jost. We found a sign that had "Captain Bob" on it. It was $75 pp & had 4 of us as guests. He was a local guy-cash only. He provided water
only & snorkeling gear. We had a blast. Low key, sailed around St. John.
Look at my post above if your serious about day sails. The locals always know...