Sailing

Despite be a life-time power boater (and occasional sailor) I have recently become MUCH more interested in the idea of sailing. So being an experienced 'water' guy that wants to learn more about sailing, what would be the best current experience available for us in September?

If you are interested in sailing around SXM, I don't know the answer to that. If you want a sailing experience I would suggest the BVI, especially for first time experience. It is great sailing and much easier for a first timer. Post on the BVI forum if you are interested. BVI is just beautiful for sailing as you are always in sight of land. Very informed sailors on that forum to help and answer any questions and give you good advice.

Right now, I expect this might be it. https://www.bluebeardcharters.com/arawak-boat.html

The charter fleet that was based in Oyster Pond was destroyed. But it will be rebuilt, just not by September.

There are several marinas around the Lagoon on the Dutch side. I would suggest stopping in and asking at the desk. The staff will be able to help you find a private sailboat charter.

But remember that your options will be extremely limited since September is the height of hurricane season and most prudent sailors are not in St. Maarten

Looks like you live in North Michigan, so you should be close to one of the Great Lakes? Possibly find a sailing club that gives lessons. I know our yacht club, NCYC in Lasalle, MI has adult sailing classes.