The first thing is a good set of binoculars. We have 7x50 (recommended), and have accumulated 10x42 (great for birding), 9x63, 7x60, and 20x80 through the years.

Our first scope was an inexpensive Celestron 114 with auto star finding and tracking.

This lead to the 12" Orion Dobsonian with the digital star finder. We have found the Telerad sighting device easier for most situations. But it's nice to have the go-to capability in a pinch.