The drive from Manhattan through Queens will give you the chance to witness the scenic transformation from skyscrapers and concrete, to fields and greenery as you enter Long Island. You'll pass the famous Long Island Duck building before arriving to world-renowned, glamourous Southampton--the oldest of the Hamptons towns. You may even spot celebrities like Jerry Seinfeld, Paris Hilton, David Letterman and Steven Spielberg wandering around. Stroll down the photo-worthy main street, before going down to the the historical area and harbor.
After, visit one of the oldest and best wineries in Southampton, where you can sample different, delicious wines. The next stop, Sag Harbor, is a small village full of rich history. Walk around the harbor and watch the yachts along the water. Stop at the antique stores or the old-world boutiques for some vintage shopping. After lunch there will be a stop at the Tanger Outlets for more shopping, before an evening arrival back in New York.