1st flight - Oshkosh 1998 T-6 - Very Early one morning, while volunteering on the Warbird Line Crew (which I still do every summer), a thoughtful and kind pilot placed line crew volunteers in the back seats of four T-6's going up for some formation flying practice. Great pilots and a picture perfect summer day - blue skies and small puffy clouds, smooth air, great formation flying.
2nd flight - B17 - just a few years later in EAA's Aluminum Overcast flying out of New Bedford, MA on a clear and crisp autumn day...first flight of the morning, down the coast to Newport, RI & back.
3rd flight - L17 - over Naraganset Bay, RI in a Navion on a clear spring day.
What I would like to fly in? Almost anything, anytime, anywhere I can get to...but I hope one day to ride in FiFi.
If a "fantasy" counts, maybe a B36 just to feel flight in something that big and that noisy.
Or...perhaps the Vickers Vimy? Kinda big...kinda slow...kinda noisy...and in the front (gunners) cockpit, of course.