I added a new concept design png to show how the Havana Nights Party angle could be incorporated.

Our regatta committee chairman has indicated that he wants to incorporate the Havana Night Awards Party flair to the poster but he does not want it to overwhelm the basic sailing offshore overnight by moonlight theme.
A fedora, a cuban cigar, some tropical foliage, a rum cocktail all are potential elements for that awards party notion. Our sailors are predominantly male but our committee includes some conservative older ladies who may be turned off by the inclusion of sexier elements that might appeal to the masculine crowd
The moon, and sailing and regatta name element will be added to a white t shirt for sailors to wear on hot Texas days, so that element would get greater approval if it can be easily adapted to printing on a white T-shirt without the need to do a full white under printing. (Sorry , I do not know the technical term but you all have seen tshirts where it feels like plastic behind the print.)

Hello, this looks like a fun project. What size will the poster be printed at? Common sizes are 18” x 24”, 24” x 36” and 27” x 40”.

18 x 24 is about right. Typically the bottom 25-30% will be sponsors. The T shirts will not include sponsors and some posters will not include sponsors and will be printed suitable for framing, so those will have a lot of extra white space.

We have some really nice designs that have incorporated the Havana Nights flavor. Before time runs out I would like to open it up some to unfettered thinking and fresh concepts from the artists among you that will make an eye catching design on a white t shirt. Just a full moon, a modern racing or cruising sailboat (could be abstract), Harvest Moon Regatta (include registered trademark symbol), the dates October 6-8, 2022 and the 35 either as text or incorporated into the art. Aim for a square layout so that we can add sponsors and party details under it on a portait shaped poster, or incorporate blank space for sponsors within your design.