As far as going to Crete, when we went we just had to sign up (must be on leave) and show up on the Wednesday it came through to see if we would get on. Usually no problem, because so many people get off in Naples and not that many get on to continue. There is a little travel place across the street practically from the terminal in Souda and they can arrange hotels and rental cars. They have a small fleet of their own cars that are not pretty, but they run and they're cheap and they will leave the keys at billeting if you are coming in after hours. The first time we went we got in around 4:30 pm and they had our car and directions to the hotel they had arranged for us ready. We stayed at the Lena Beach hotel and it was your basic hotel. 2 dbl beds, fridge, tv and a little balcony that looked out at the beach. It also had an awesome fresh water pool. They have a little restaurant but we didn't eat there. We had 2 nights there and then had n 8:30 am showtime for the rotator back on Friday. This was in July 07. The second time we went the rotator was late leaving here and we didn't get in until about 10 pm. The car keys were waiting for us at billeting. This was spring break and I had arranged a hotel at the beach through Expedia. Low and behold we get there at 10:30 at night to find out the hotel isn't even open for the season yet! Luckily they also owned a brand new resort on the hill and we stayed there for the same price. Friday the show time was 6:30 am, so it was just about a 36 hour trip that time. With 2 kids, not so much fun. Souda used to have a policy that families couldn't stay in the barracks/billeting because aircrews stayed there and they didn't want the noise, but I just heard that that's no longer the case, so if you wanted to stay right on the tiny base, you could. Also, if 36 hours isn't enough, you can always catch the rotator from here and take it back the next week into Sigonella, then try to catch a hop or commercial flight up or a train, which I have heard don't cost much at all.
Even though we haven't been there long enough to do more than shop for a day and swim, I like Crete and it's a nice short break (And it's FREE to get there). July isn't quite the high season yet, so it's not overly crowded. If you go for spring break, besides the hotels not all being ready, most of the beaches aren't cleaned up yet, either. And it can be a little chilly. When we were there in April 08 we walked around in Chania and most of the shops were open and had great pre-season prices on some things. The Samaria Gorge wasn't open yet, because all the snow hadn't melted and there was a risk of flooding for hikers. We were happy to wander around Chania and shop and then eat at our favorite restaurant that night.