There are no packaged tours for what you are asking. If you are interested in having someone else deal with the gear and arrange a good location for the day, I suggest you contact several of the smaller half or full day sail charters out of Red Hook. Check the STT/Daysails pull down menu located at the top of the page to get started. Once you have initial idea, come back and get comment from this board about specific charters.
If you want to do it alone, you can get the Red Hook to Cruz Bay ferry (schedules and rates link at top of page) & gear can be rented in Cruz Bay. Then you can get a taxi to Trunk or any of the North Shore Beaches. Hawksnest and Cinnamom are also good.

Before I get corrected, while I am sure there are several people who could put something together for you, it is probably more cost efficient to use the existing charters or do it yourself.