It would probably be best to stay in contact with your sailor. He should have all the details. He will probably have to walk to the gate where you will be waiting.
Jeffrey, when our son was at Pensacola, until January 2017, we didn't have to sign him out if he was with a buddy but they both had to be back at the same designated time together. Jim is correct though, have your sailor check on it. We went for AirCrew graduation and he had it set up to get us on the base. He will give them the information on you and you will have to have ID and Insurance card even if you are renting a car. He was supposed to be able to call and get us through but that didn't work so well. What happened then is just past the check station is a visitor service center where you have to pull into to get an approved day pass, with the information our sailor gave them. Then we would drive to the barracks which were across the base. Walking is a long way for them to get to the gate. On our way out after graduation we stopped and got a pass for the week so we could get in everyday. If our sailor was by himself then we would have to check him out and back in. It was really quite easy. Does that help?
Thanks Dale. I really had no experience getting on base in Pensacola other than touring the museum. I do remember however that we had to get a pass to get on base in Jacksonville.