I've seen it before but did a little research(the internet, what a tool). This is HIGHLIGHT, launched in 1960. I would bet this photo was taken soon after. The new boat owner was Donald Clarke Watson. Typical new boat buyer of that day. Watson knew a lot about sailing; he grew up sailboat racing. He paid around 30k all equipped(a lot of $ in the day). The boat was designed to race, and race, he did.

Here's the glamour shot every racer looks for:

Reading his obituary, he would have been about 45 in this photo, still a typical new boat owner age, today. This crop shows 60's state of the art racing. 5 man crew, young to middle aged. I know from my sistership, all the parts are near new. State of the art then, right down to the strop preventer(which I still have). These boats were a lot of work to race often with another headsail flying(spinnaker staysail-I still have one)

Here's a crop showing everybody moving.

Watson was soon hooked on Bermuda racing (of serious 60's racers, who wasn't?). He did well with Alden Challenger HIGHLIGHT and 5 years later, launched his new Alden Caravelle (42' more powerful ocean racer) in 1965. I find that time frame pretty typical of new boat owners these days so things haven't changed much there.

Watson sailed(some power toward the end) nearly into his 90's(died about 91) and spent a lot of time sailing to Maine from Mass.

Some inflation figures: 30k in 1960 inflates to 240k today. Not a huge amount for a new boat today, even a new 38'er.