Here are some ideas:
Auto-inflatable life vest--more comfortable and lighter than a regular vest ($150)
Digital racing watch ($100)
Small handheld VHF radio ($300)
Good pair of sunglasses ($100-300)
Sailing duffel bag (Harken brand is nice)($60)
Go to www.resails.com for sailing gear--I got my wife a jacket made from old sails--expensive but very nice ($200-300)
Any sailing clothes--boots, shoes, t-shirts, etc...
This is a start.