My daughter and I stayed on the Tradewinds floor last summer and I think it was well worth the extra costs (by the way, if you have a family I believe they have recently begun age restrictions for children under 12). The staff of the Tradewinds club did a great job of taking care of our needs. They get to know you throughout the week and provide a level of service not typically available in a large resort property such as this one. The food was good (not amazing, but good) and we ate there every day, but you will likely want to go out to dinner a few times because the club serves more of an appetizer type meal at night and not dinner (a couple of times my daughter didn't like what they had out for lunch and they made her a sandwich, which was a nice touch). Also, the free bottled water and sodas available all day really came in handy...especially when you spend a lot of time at the beach. Let me also add that we did not book for the Tradewinds club ahead of time, but rather upgraded once we arrived at the hotel. I don't remember the exact amount, but I think they let me upgrade on the spot for around $100/night which is less than what it costs at the time of booking. This may have been because of lower occupancy during the week and it might not work for you, but you might want to consider trying to upgrade once you get there. I will say that the level of participation in Tradewinds seemed to be a bit sparse when we were there...which only added to the allure of it. All in all, I would do it again and wish that Marriott would add these to their other resort properties. We are going to the Cayman property this summer and I really wish they had something similar.