Originally Posted by Stacy

Glen's Ride to Montauk and 5BBC's Montauk Century both pass Jerry Seinfeld's mansion of Further Lane. They may pass Lasata where Jackie Kennedy Onassis spent her childhood. But I think the former residences for Martha Stewart, Calvin Klein and Grey Gardens are off the route and I don't even know where Diddy's Southampton digs might be. The problem is that neither of these rides actually tell you whose mansion is where so you may want to do some research.

There's another one called the The Mansion Ride that includes mansions in Nassau County. Or you could just download some bookmarks from the Google EarthCommunity and make your own tour.