I know that Baofeng HTs are popular because of how inexpensive they are but I don’t recommend them to people whom are new to amateur radio. If you’re serious about keeping in contact and need a solution that will go further than ~3 miles I would get a Yaesu FT-2900R (on sale now and also has a rebate) and a Comet M-24M magnet mount antenna for your vehicle. You will need a amateur technician license to transmit.
With that radio and antenna combination you can expect a typical range of 30 miles point-to-point without a repeater so long as you don’t live in a mountainous area. Yes, you will get less range if one or both vehicles are in a poor position. With repeaters you can easily cover 100 miles. My personal record point-to-point on the 2m ham bands is 120 miles using an omnidirectional antenna at 55 watts.