Difficult question but i think my fineline mini zombie or a DT1 or Tudor diamond tail egg (which I’ve had the chance to buy it back several times but stupidly didn’t).
More regret not buying a Mandala Clandestino (which dutchsurf bought)a tudor papa joe and a Bing pintail lightweight when i had the chance cause those boards are rare here in europe....
6'0" McCallum Bonzer and 9'6" Mitsven Magic more than anything, but not enough to get really hung up about it.
They come, they go.... and I do not have the time nor space to deal with lots of boards, nor do I get satisfaction from hoarding for hoarding's sake, I think I like to make use of a board or get shot of it, let someone else enjoy it. Although I do understand that people do connect with surfing strongly just by having a board or set of boards in their possession and that's fine, just not my thing.
I keep trying to whittle things down to 3 boards to keep life simple, but something interesting always pops up to try.
I have been more gutted when snapping boards I think, which is probably stating the obvious, but there is nothing worse than having a board that you are love suddenly taken away from you.
The board I most regret selling is a Matt Calvani wingnose he shaped for me almost 15 years ago.. same color as rockford’s car and 9’5 so if it’s out there hit me up. Flat as an ironing board, heavy on a good way and has early sixties bing logos on it..I also had a vintage peck that is in sea isle that was amazing as well but I like the story of where it went
I needed to raise some cash to get me out of a hole a few years back and concluded one of my boards must go. On the last-in-first-out rule it had to be my Jim Phillips Bastard.
I sold it to a local guy with a verbal agreement that if he ever felt the need to move it on himself he'd get in touch with me first.
Fast forward a year, my financial situation had improved and I was regretfully thinking about what to bring into the quiver to replace it. After a surf around this time I got out to find message on my phone from said guy, honoring the agreement with an offer of first refusal. The next day it was home!
I can tell you, the joy of riding that board for the first time, for a second time, was special!
All of them!! Got a few of the good ones back over the years.
Worst regret is a 9'2" Cooperdesign Malibu Foil pintail clear. Traded it for a DT-2 that I thought I would like better, but I was wrong. I would buy that board back in a second and I think it is in Long Island somewhere last I knew of it.
I most regret selling my first surfboard to fund my second longboard. It was a 6'2" Jeff Crawford single fin that was handed down to me. Kind of fishy in the shape with small wings and slight swallowtail, I'm thinking it was probably from the late 70s? Not the exact one below, but similar. I didn't surf well enough at the time to surf it well, so I didn't feel bad about unloading it at the time. I think I would have had a lot of fun on it now.
(LOL to that wax job. Wax conservation.)
A bigger regret is a board that was never mine and one I never even saw -- my dad's 10' Gordon & Smith. He got tired of bumping into it in the garage and finally gave it away to the kid next door a few years before I was born. No pictures exist of it, just descriptions. I have always thought that it was a Hynson Redfin, but it also could have just been a three stringer stock model with a red speed fin glassed on. It's my white whale. I've tried tracking down the guy he gave it to, but no luck.