Typically an overnight last anywhere from 12-14 hours.. And dining arrangements should be made according to the lady's preference for example perhaps she may want to go out or stay in. Also, if you are dining out, ask her what type of food she prefers, I assume you already have a clear idea of what she likes after various dinners together. Keep in mind that an overnight is not an occasion to "wear the lady off" rather, an extended engagement where you can enjoy her company without having to worry about the clock. Make her feel comfortable, have water, snacks or anything she can possibly need on this outing outside of her home. Generally within dinner, private time etc.. You should consider 6 hours and the rest is sleep time so she can be functional the next day. Play time will more likely happen twice, after or before dinner and in the morning. Give her space.. Let her get ready and beautiful for you the next morning and if you snore (trust me some people may not even know they do) be mindful and inform her so she can make the decision on whether she could sleep in the same room or not.

Aside from that little bitty difference that I'm paying her for her time and that it isn't a real date (or paying her to leave after the session is done, depending on how you look at p4p), I tend to do the same activities and routines I'd do if I'm on a real date.  

I've started my overnights anywhere from dinner time to 2am or so. The girl and I would get together for dinner/drinks, club, beaches, strip clubs, concerts, or whatever else is going on in the town.  If we don't spend too much time outside or doing other things, it's fun to jump in the hot tub together with some liquor (or water lol) within arms reach. Dim the lights a bit, open the curtains (if the bathroom has an outside view), and just talk and fondle. I always forget to bring LED candles but candles do set a better atmosphere if the girl has em. After a round or two, we just chill in bed with the tv/music on, talk & cuddle til we  get horny again for another round if we can squeeze it in. Sometimes I'm amazed just how little cum squirts out by the time I'm done before we go to bed. lol  

Some ladies want about 7-8 hours of sleep minimum but some are more flexible and hardly sleep accommodating more action. I try not to wake the girl up too early but for me, it's more like 5 - 6 hours due to some level of excitement preventing me from falling asleep right away, some mild natural discomfort sleeping in same bed with a girl I don't even know the real name to (if it's the first time with the girl), and random hard-ons that pop up when sleeping next to a hot babe with barely any cloths on. Doing overnights for the first time, even with a girl I've seen before,  still gives me a little bit of discomfort/anxiet on first night but maybe that's just me. First time overnights are like that for me.

In the morning, we may take a quick shower and possibly go for another round or two in the morning.  If time isn't up by then, breakfast or lunch. Sometimes the girl may stay a few more hours, if she doesn't have other plans.  

If you're gonna spend time outside, it's really important to plan in advance exactly where you're gonna go so you're not wasting time figuring out what to do, lost in the middle of nowhere, or looking for parking for 25 minutes. (That happened to me lol) Time is expensive so plan out the evening well...  

Have fun!