Idiot Proof Buying Guide
Orion XT8 Dobsonian Telescope: $380 shipped
http://www.amazon.com/8945-SkyQuest-Classic-Dobsonian-Telescope/dp/B001DDW9V6/
... And that's it, really. Comes with everything you need. Comes with a 25mm eyepiece, comes with a finder scope, comes with a focuser that can take 1.25 or 2" eyepieces in the future. Even comes with a license for Starry Night which is amazing software.
The only other thing you probably NEED to get started is this book,
Turn Left at Orion - $20
http://www.amazon.com/Turn-Left-Orion-Hundreds-Telescope/dp/0521153972/
It has a good intro for scope care, setup, teardown, etc. and then walks you through all the neat features on the moon, and the best time to look at them.
The rest of the book is broken up into "seasons", so now that it's fall, you go to the "Fall" section of the book, it tells you what constellations are up in the sky, and then tells you what neat things you can see in that constellation, and then rates them based on how cool they look via binoculars/telescope. This entire book assumes if you have a scope you have an 8" dobsonian, and uses that as a reference point. A++ Would buy again.
Finally, I would pick up a
green mother fucking laser pointer (like $10?)
http://www.ebay.com/itm/Military-5mw-532nm-Zoomable-Focus-Burning-Green-Laser-Pointer-Pen-301-Battery-/261717915353?hash=item3cef9a76d9
Your james bond fantasies come true. The beam is visible in midair, and MOTHER FUCKING SCIENCE makes it seem like it stretches all the way to the stars. You will impress everyone (including yourself) and it will make pointing things out in the sky 10000x easier.
Extra things you may want:
Extra eyepieces:
Here you have some options. I ended up going with a "starter kit" and while it's neat, I find that I actually don't use hardly ANYTHING from this kit anymore. They were great for figuring out what focal lengths I liked, but once I figured that out, I bought one "nice" eyepiece, and that's really my go to eyepiece, unless I find I absolutely need something else.
Massive starter kit - $180
http://www.amazon.com/1-25-Inch-Premium-Telescope-Accessory-silver/dp/B0069VXRLS/
The one eyepiece I actually use,
Meade 14mm ultra wide angle eyepiece - $129
http://www.amazon.com/gp/product/B005HSPUVO
Long story short, it's a "wide angle" eyepiece, so you can see everything that the 25mm that comes with the scope can see, but 14mm will "zoom in" further, so everything is bigger, sharper, clearer. Good stuff.
Telrad finder sight - $39
http://www.amazon.com/Telrad-Finder-Sight/dp/B0000ALKAN/
This baby is awesome. It makes 3 rings appear in the air that make "star hopping" much easier. The included finder site is good--but the red dot can cover up what you're actually trying to find. The telrad solves this.
---
Honestly though, just pick up the scope and the book for now. And maybe the laser pointer. $400 all in. If you can, attend a star party near you, or try to get involved in a local astronomical society and see if you can try out some different eyepieces before buying anything.
That's what everyone recommended to me, and I said "no, fuck you, yolo, etc." and bought the big $200 starter kit, and barely use any of it.