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You got it! Calasetta will be the site of the 2023 RS Aero Worlds in July. https://www.rsaerosailing.org/index.asp?p=event&eid=2477 Your go @Cod

where in the world

Thanks @Cod - Couldn't have got it without your clue about "icebreaking railway, vehicle, and passenger ferry."

Columbia YC, Chicago

New York

Cape Cod

Correct! Your move @Cod

where in the world

West Lancashire Yacht Club https://wlyc.org.uk/ Also at WLYC during the 50th 24 hour race in 2016

Well done @dgibbsmi . I take my hat off to you. Great puzzle @dogwatch !

Now I'm really confused. The Beatles did play at somewhere close to the place I'm thinking of three times in the 60s. How can that be the wrong era? Was the target club founded more recently than that? Or had it been closed down by then?

Sorry. I couldn't find two authors (defined as people who write books) associated with a famous building near where I think this place is. But I did come across a hotel where the Beatles stayed so I guessed them. Not about not wanting to play. I spent most of the morning searching for authors...

John Lennon and Paul McCartney? They have been here, there and everywhere.

No idea. Ever since the classic Firefly was dropped from the Olympics to make room for all the fat boys in the Finn, I have lost interest in wooden boats. That one looks like a real clunker.

But the original is so much more attractive.

Not Siberia Seems to have been taken before color photography was commonly available. On the other hand, the Toppers say it is post-1977 and somewhere in the British Isles.

I am not really a sailor. I just play one on the Internet.

It's been a while since I sailed the Laser Masters Worlds in Siberia, but this does look like Bil'yardnyy Klub Metkiy 1-Ya Krasnokazach'ya Ulitsa, 119 Irkutsk Irkutsk Oblast, Russia 664081

Russia?

Montana?