If he likes looking at the night sky I don't think you could go wrong with a good dobsonian scope (a newtonian Optical tube mounted on a dobsonian mount). For $1000 you could expect to get a reasonable size instrument (10 or 12 inch) and some eypieces. Dob's are basically reflector telescopes, they're inexpensive, give maximum bang for your dollar and are easily set up and used. With telescopes size is everything, ignore claims of high magnification, they mean nothing, quality of optics and size are all important. An 8 inch dob is a good starting point, 10 is better and so on. It's worth noting that dobs aren't compact so it may be worth a trip to your local dealer to check sizes. To get an idea of prices it's worth visiting the
Bintel site and
Andrews communications site. They are the biggest dealers and have the best prices.