St Thomas or St Maarten as noted. And did you ask for lectures on what to bring? If you have the time, Crowley or Tropical will add it to a container. You'll need a broker at your end to handle it. Masterpiece in Newport RI does it for a living Lots of locations worldwide

Get it sent sooner than later and the agent in the islands will have it cleared before your arrival. STT and SXM are both duty free ports so less paperwork than if you tried to send it to Tortola

Your question regarding "Will it show up?" using the airline is very likely a yes, in time. The small planes get full so some bags don't always make that flight. Typically on the next one or the one after.

I always had the luxury of sending my kite, scuba and SUP gear in our own containers. So nice having your own kit.

Hope this is helpful