That sail sim site is great. You can create a race anywhere to anywhere (on the water.) it's all accessible through your Web browser. races across a sound, or around the World.
I've been sailing on this game for nearly a year. I've done around the world 3 times. It's a fantastic group of people in the game and on IRC. I recommend definitely recommend it.
I agree that it’s confusing. But Virtual Regatta has been around since 2006 and is probably the most prominent online sail racing community after SailX dissolved due to malicious hacks.
Back in the mid-1980s I recall playing a sailing game -- Wooden Ships And Iron Men" -- on the BSD-4.2 based Stride "supermicro" (68000 CPU, 80MB hard drive, can't remember memory). It was a multiplayer battle game simulating 18th century sailing ships and their arms and armour. Weather was constantly changing, and you certainly had to take into account wind, sea-state, time of day, different sorts of ammunition you might prime your guns with, etc. And all that on a (well, a few) 40x80 ascii terminal(s)!
Very challenging and entertaining game. Always wondered why the theme/code was never expanded upon using modern hardware and software.
https://8bitbyte.ca/sailnavsim/