Picture looks to be early 60's; pre-trapeze. Location Annapolis; Frostbite sailing. Skipper and crew unknown. Male and female teams were very common in the 1960's (hard to tell from the photo if this is a mixed crew).
Bald but my eyebrows are growing at a prolific rate. Sailed Windmills and Y-Flyers in the 1960's. Founded Miami University (OH) sailing team. Sailed International 14's and Lasers in the 1970's. Sailed International Canoes in the 1980's to mid 1990's. Sailed Classic Moths since 2002. Enjoy boatbuilding though I'm very, very slow at it (the Internet doesn't help matters).
After choosing this username (Tweezer is the name of my Classic Moth), further research on the Internet turned up that Tweezerman is a corporate name for a line of pedicure products. Let me emphasize that I do not work for, nor endorse these products.