What's the coolest thing you've done in an airplane?

Renting a Duchess and flying to Paso Robles with my brother and good friend to go wine tasting. Then going up for a quick joy ride to circle around Hearst Castle and then fly up the beautiful Pacific Coast.
 
going down a canyon on a drop in the Rockies, a tree lit up off the starboard side...I felt the radiant heat from it torching; that was cool. We also saved a house and a number of outbuildings on a farm before the ground firefighters got there...that was pretty fulfilling.
 
Flying in a Stearman biplane with the Red Baron Pizza Team. (No longer doing it for this Pizza company).

We were a flight of two, doing aerial photography plane-to-plane over some southern California mountains out of RVR.

The pilot (over 7K hours!) settles me into the front seat, says not to touch the pedals, and buckles a seat belt. I ask if this is the one to take off if we have to bail out. His reply: " No, that's your parachute." He buckles the other belt and says "It's this one." They are different colors, and I'm very glad I'm not color-blind.

His safety briefing includes: "If we have to get out of the aircraft, I'll say, very clearly, 'Bail out! Bail out! Bail out!' three times. Unplug your headset (built into a very cool leather helmet!), take off the RED seat belt, not the GRAY one (or maybe I'm remembering it backwards. I damn sure remembered it for the duration of the flight!) and jump out. Try to miss the tail of the plane." OK, I said. He continued: "If you forget this, it's printed right there on the dashboard." and sure enough, there's a 2"x3" engraved plastic plaque with the same text. Like I'd stop to read at that point.

He shows me the mirror strapped to a strut so I can see him in the rear cockpit. I'm thinking, "What if I look in that mirror, and he's NOT there?". I look around for what part of the aircraft frame I could break off and jam in the stick receptacle - these aircraft were dual-control trainers back in the day - stick now removed so I couldn't get him in trouble. Fortunately, I didn't need to.

Both pilots were true careful professionals, practicing their aerial ballet for the next day's air show, even though they'd done it many, many times before. Of course, I did enjoy the loops, hammerheads and other acrobatics. Footage was great, too.
 
I'd been waiting to post this one. As a big racing fan, getting to fly the Daytona 500 was really, really cool today.

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I got to take my wife flying, her first time in an aircraft of any type. Thankfully she loved it. We also "went to Denver".
 
River running at 1/2 wing span alt. Flying between the rocks of the SW desert. Flying the entire west coast from Roche Harbor to Brown Field (San Diego) in 2 days, never higher than 500 agl (having to climb for TPA at fuel stops). Taking up an ancient birdman (a WWII ace with cancer) and giving him the left seat. Taking up a French WWII resistance fighter and having him weep in joy of flight and expressing his thanks for the Americans. Flying 5 SEALs to scout the terrain in which they would spend the next 2 weeks for a reunion. Taking a Navion non-stop from OK to coastal CA to shoot the expected ILS at night to within 10 minutes deviance of ETA (calculated back in OK). Flying a perfect ILS the first time. Flying a circuit around the country during the fall. An aerial tour of following the changing of the leaves. Breaking out on a messed up ILS at an unfamilar aprt in totally crappy wx with you-got-to-be-kidding-me cross wind and finding I wasn't that messed up because the aprt is almost on the nose. Finding out it was my 3rd ice encounter. (thanks, KHYA) Building my own VOR-A to a friend's field in mtn terrain then maybe flying it in LIFR to find it worked as planned. A short field landing so good that TWR at first didn't believe I cleared where I did. Taking a 172 to 17,900 just because. A 13,500' DA take off in an ancient PA-28-160 just under gross and being thrilled my calcs were spot on. Having almost 2 weeks to play around in a friend's Super D. Never intentionally scaring a passenger. (And likely a whole bunch of other good things.)
 
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