Range is a matter of selecting the right band for the time of day. I've worked Santa Barbara with a 1 watt VHF handheld using a rubber duckie...from San Diego. Ducting effects over the ocean. I had a chat with a Swiss ham around 1 PM on 10 meters...using a 4 watt mobile rig and mag-mount. Check into QRP (low power) operation. It is a passion with some people.
My favorite activity is transmitter hunting. My wife and I participated in many hunts while we were dating. Our hunts started at 5 PM on Saturday afternoon from the Sears parking lot in Chula Vista. Odometers were recorded for each participant. The boundaries were drawn at the San Diego County line in all directions. The winner is the person who finds the transmitter in the fewest minutes and fewest elapsed miles on the odometer.
I agree with the QRP recommendation. You would be surprised what low power can do with the right antenna and conditions.