While in Charlotte Amalie on a cruise, we independently booked a sailing trip with OnDeck at their office next to the cruise pier at Havensight Mall. We got there just as they were finishing up their morning trips with cruise ship passengers. We paid more ($99 per person) than we would have paid booking through the ship ($89 per person) but we also got to go out with just the four of us in our group. The other boat went out with only OnDeck crew to race against us.

The ships appeared to be new and in great condition. Our group (four guys in fairly good shape in our mid-30s) all had a great time and were able to participate in several tasks for sailing the ship.

We were actually out on the water for a little less than two hours. I think it was advertised as a three-hour trip, so I'm not sure if they count some sort of on-short orientation we didn't get. Coming in as we did at the end of the day, maybe we got shorted a bit.

The crew was friendly, professional, and entertaing. The race part, itself, was interesting and fun, and we ended up with a tour around the bay before heading back to the dock for a rum punch (on board, they serve water or soda).

All in all, even though it was pricey, I'd do it again at that price as long as we had the boat and crew to ourselves.