We did this in Jan and it worked out well. My kids had a late afternoon flight so we took a slip at American Yacht Harbor in Red Hook and overnighted there. Nice marina and an easy pick up spot. Another good place to meet is to pick up a ball at Caneel Bay and let the kids ferry to Cruz Bay then taxi to the Caneel Bay resort. Very nice restaurant and bar there. Might be easier than taking the dinghy to Cruz Bay for the pick up depending on time of day and amount of luggage.