My two cents.... We fly from Kansas City, and like many Midwest cities you can't get there from here (easily). The first two years we booked the Delta through Atlanta route and tried to fly all in one day. After losing a day of vacation due to weather and a missed connection in Atlanta, we now fly one evening to Charlotte, spend the night in a cheapie hotel near the airport, and catch the nonstop flight to SXM out of Charlotte the next day. When we are on our way home we just try to do all the travel in one day and if we miss the connection we've just extended our vacation by a day.