We always plan our trip. A trip to the City for a special occasion would normally include a theatre show, concert or dinner for us, so it would be impossible to ' wing it '. Most of these require booking at least 6 months in advance, if you want good seats, and not ones behind a pole. We always book dinner, as a seat at a good restaurant, close to the theatre/ concert venue might be hard to find, and we do need to eat before the show. Sometimes we stay in the City overnight so we obviously have to book a room before we go. We need to know that we have a bed to sleep in, in advance. It would be a shame to ' wing it' and find there are no rooms available. It is great to be spontaneous, but for special occasions where you are going for a certain reason, you need to plan. It would be a shame to have the good intentions of going to the City for a special occasion but arrive only to find there is no where to eat nearby and no where nice to stay at the end of the night. A lot of shows don't finish till around midnight and we are often too tired to drive home then so need somewhere to stay. It would be a shame to have to be turned away. It may not happen, but I would prefer to know for sure that it wouldn't. There's a time and a place for ' winging it' and a special occasion is not one of those times.