During the Cuban Missile Crisis, the US took photos of the nuclear warheads by using aerial photography. Were there any instances that Kennedy sent special forces into Cuba to photograph the missiles up close?
There were two primary types of photo reconnaissance operations during the Cuban Missile Crisis: those taken by very high-altitude U-2 spyplanes (which took photos like this — top-down, not very high resolution), and those taken by low-altitude, very fast jets (the RF-101 and RF-8A, which took pictures like this — slant view, very close up).
These were the only photographic missions undertaken during the Crisis. Kennedy would not have dared sending special forces onto Cuban soil, where their capture by either Cuban or Soviet forces could be seen as an act of war during an already tense period. As you can see from the low-level photographs, they are pretty close as it is. (I got to hear one of the pilots talk about his work at the time; he said it was a good thing that Cuba was relatively un-electrified because it meant he only had to worry about tree tops — that's how low he was flying! The low-level planes were about 500 ft off the ground, going 600 mph — too fast for indigenous Cuban forces to shoot them down, though the Soviets on the island could have, if they dared. This photo is pretty remarkable in that you can see the shadow of the reconnaissance plane in it.)