The scenario you describe will require a repeater due to line of site limitations. A repeater has a high antenna and, as its name describes, receives on one one frequency while simultaneously repeating on another. This setup can provide reliable communications over 30 miles or more, versus maybe 5 miles at best between 2 walkie talkies without a repeater.
There are plenty of GMRS and Ham Radio repeaters out there, and an assortment of reasonably priced walkie talkie, mobile, and base rigs for both. Waterproof handhelds are also available. For Ham Radio you would need a Technician class license which requires passing a 35 question exam on electronic and radio theory and rules and regs. The questions come from a published pool and many people have passed just by memorizing the correct answers without understanding the theory (which is unfortunate). There are many resources and practice tests availble to aid your study.
Though GMRS also requires a license, it appears that since 2015 there is no longer a fee and a license can be requested online. For GMRS repeaters can be open (for use by anybody) or closed (dedicated for a specific group of users though they may allow others to join for a fee). If there is an open GMRS repeater with the coverage you desire, this is the easiest solution.
+++EDIT+++ The 2015 FCC change only eliminated the regulatory fee but not the license fee. A license will cost $70 and is good for 10 years.
Apply here:
https://www.fcc.gov/wireless/systems-ut ... ing-systemPeter