On our trip two weeks ago it wouldnt be possible to do what you suggest. We had 30+ kts out of the ENE - E for three days and the SFDC was rolling with 3m waves. Id suggest, as other have suggested, that you do a typical itinerary and have your friends take a taxi to trellis and jump on the scrub ferry. Super easy, and plenty of places to explore at trellis if they have some time to kill before the next ferry.