Here is a nice, though long, day trip from Jerusalem:
Navigation is reasonably straightforward for all but the final Jericho/Wadi Qelt bit. There aren't too many roads in the desert. Thus you could take a rental car with confidence if you don't wish to spend the big bucks ($300 or so) on a guide and car for the day.
Here's a comparison of the snake path and the cable car in the same frame:
Herod only came up to Masada once or twice. The place, however, was fitted out with massive stores, ample water, and hot baths. The view from every part of the palace is superb:
The fame of Masada rests upon the Roman siege of the fortress from AD 70 to AD 73. The Romans had 10,000 men; the Jews numbered only 1,000. When the Romans were on the point of conquering Masada, by dint of having built an earth ramp up the back of the mountain, each Jewish man killed his family and then himself.
Best to take the cable car down now...
The stared-at hill contains caves in which jars of linen-wrapped scrolls were hidden in AD 68. The scrolls dates range from the 3rd-century BC up to the Roman conquest of AD 68. Some are portions of the Bible. Some are records of the monastic Essene sect, which had withdrawn from a corrupt society to live simply in the desert.
If you're lucky, on the way north toward Jericho, you'll pass Bedouin herding camels:
It is easy to see how Jericho would have been a very attractive oasis to those who'd been wandering in the desert:
Now let's go up Wadi Qelt to St. George's Monastery...