I've seen 20" Dobsonians break down and pack into the back of a Ford Festiva before. Keep in mind that these things are 10+ feet long when fully assembled.
I am not an expert but I like to take my (nice) binoc's out and view the stars. I've been to a few star gazing parties and really like the Dobsonian-style telescopes. You can build your own (from scratch or via a kit). Deep sky and planetary observation is excellent with these units (they...
Dan's advice is gold. Get some binoculars (10x50 w. hands or 10x70 w. stand... both with BAK4 lenses) and JOIN A CLUB. You will get to try out everyone's scopes (certain designs are optimal for certain uses). Additionally, you will probably stumble onto some used gear for a great price...