I deployed in 2014 to Guantanamo Bay, Cuba, and I actually mailed my road bike down there. I got in something like a dozen or 15 rides in while I was there. I never rode in any of the sensitive areas, but it's a naval base that's been there since 1903 or so, and I rode all over that. There's a hill there with 200-300 feet of climb that doesn't sound like much, but at its steepest point my Garmin reported a 23% grade. I only rode that once, because with the cassette I had on there (I think it was my 13-25) and the 34t chainring it was absolutely brutal and just about killed my knees.
There was one abandoned camp called Camp X-Ray that I rode past quite a few times. It's where they kept detainees for several months back in like 2002. It's at the end of a long road, and that was essentially the turn-around point.
I wish I'd ridden more there. I mailed my bike back at the end of the deployment in 2015. I unpacked it and never touched it again until this past August, when I made it rideable and started cycling again. I believe I still hold one or two KOMs on Guantanamo, and there are a couple I should have been able to take but didn't.