You will have to see if they each can hit a repeater. That is the only way.
You may have to get better antennas.
I do not know your radio experience so I will assume none.
I suggest you contact the local ARC (Amateur Radio Club).
Tell them your radio locations, see if there is a public repeater between them.
Then use their frequency to listen in. If you can hear them you probably can send to them.
If both can hear well, then program the radios for the repeater and try in real life.
Be aware that both of you will need a Technician class HAM license assuming you are using a HAM repeater.
If the above fails you will probably have to go to base stations with more wattage power and real antennas to hit any repeater within 60 miles or so. 34 miles is a long way to go radio to radio on 2 meter handheld radios.