My girlfriend and I are headed to Jamaica in May. We'll both be 24 at the time of the trip. We're staying in Negril (a peaceful laid back town about 90 minutes from Montego Bay). We decided not to go the all-inclusive route. It would be nice to have all our drinks and food taken care of ahead of time, but we decided we wanted to be at a smaller place with less young kids and families. Plus we'll be "forced" to venture out our hotel more. We're staying at a little place right on the beach (I think it's called 7-mile beach or something). I recommend expedia. It was a little cheaper than Orbitz. We have a direct flight from Chicago, and for 5 nights it's only costing us $525 each (includes flight, shuttle from airport, and the hotel room). If we would have booked it 2 weeks earlier it would have cost about $100 less (definitely book early). Keep in mind this hotel is no frills. No TV or phone in the rooms, but it got great reviews on expedia's website.