We did the America's Cup yachts in September of 1998. It was a blast! Worth every penny. You do have to work though! Very exhilerating! We paid around $ 75 back then, so a $5 increase over 5 years isn't bad. After our sail, we asked the locals to recommend a beach. We grabbed a cab and headed to the French side of the island to Baie Rouge. Our cab driver came back later that afternoon and picked us up. He insisted that we not pay him until we were back at the ship. Turned out to be one of the best days we've ever spent.
We too did the America's Cup in St. Maarten and would also highly recommend it! They do teach you the basic skills in racing and then you take a job, either very active or less active. It can be a lot of work, but worth it, especially if you win, which we did! Definitely worth the $.
Jenni, my wife and I have done the Golden Eagle 4 times. It is great. To us well worth the price. Great sailing, snorkeling, and a blast of a party on the way back. You may want to keep in mind, the island we went to on the Eagle is a clothes optional beach. We swam and snorkeled so it didn't bother us.