We did this a few years ago, and frankly it did NOT work! The couple, who we knew very well (not well enough), did not "fit in". Gave them a copy of the cruising guide, told them to watch "Captain Ron", all preventatives. Sunsail 444 cat, comfortable, sailed to Leverick first day. They had the beach barbecue that night. After getting back to the boat, the husband started what would be a nightly routine - approached me on the tram. "She really is uncomfortable with the whole dinghy thing, could we please dock from here on out?" Of course, my answer was "Nope - no docks from here on out". Day two was her birthday, so I thought it'd be a real treat to do lobster on the beach at Wonky Dog - NOPE! "She didn't like eating outside, can we pick restaurants with AC from here on out?". You see ant places with windows? NOPE! Day three - Corsairs on JVD, chatted with friends, really great dinner - you guessed it, "Hey, I know you're friends, but Vinny is ripping you off - that meal was WAY overpriced!". At this point I quit and just had fun. A week after we got back, hubby told me that it had been "interesting", but they would not be doing it again - like I was going to ask? You do your best, but some folks will not get it - don't take it personally.
I like Vinny as well, however his Pizza’s are getting up there!