Well that's tough, there's a vast range of price point you could get yourself in to.
www.hamcity.com is a good shop and has plenty of options. A 50W + mobile radio is nice or the Jeep.
If you want to get in with minimal cost to check it out (dip your toe in)
this little handheld is a great place to start. With that radio and
this antenna you'll be in style, believe it or not this works better than your CB as long as you have the antenna pointed out the window. (I can easily get 90 miles from this if I have clean line of sight). The antenna is a must though, the antenna that comes on the handheld (and most handhelds, even $300+ ones) from the factor is crap.
Go to
www.qrz.com to take the technician class test exams. Keep practicing unti you're passing consistently then go get the license. The you can get full use of the radio and repeaters in the area without having to stress out about the more persnickity ham operators whining about yoru lack of a call.