in the summertime i do hit the Vineyard. I have 3 regulars who live there yr round and I will take a few days make a vacation of it, have a couple of dinner dates and its all good lots of fun and a great get away for me.
Now its deserted, so it would draw way too much attention to plan a visit there for myself and the clients. The Vineyard is the ultimate small town in the winter. Theres no blending in if you are a tourist this time of yr everyone knows you are there and it would be difficult. The way to make it worth the ladys time would be for a multiple hr appt a gal from the Mass area then it would be a nice escape for a night you have fun she sees only you and she leaves the next day. No ones the wiser that way. The ferry is limited this time of yr o trips to the island as well so t can be complicated as well. I think the last ferry leaves around 6 or 7 so once she's there she cant leave. Make it an over night and you could get many ladies interested in joining you