We depart New York East via the borough of Queens, leaving the hustle and bustle of the big city behind. You’ll begin to appreciate why the rich and famous choose to make Long Island their own personal playground when the scenery transforms from tall buildings to magnificent landscaping and gorgeous flowers.

Then, continue east; passing the Long Island Duck before arriving at the famous Southampton area where residents such as Jerry Seinfeld, Paris Hilton, David Letterman, Steven Spielberg, and others have made their home. This is definitely the place to see and be seen.

Stroll down Southampton’s picturesque main street before heading through the historical harbor area and along Ocean Drive, passing some of the homes of the rich and famous along the way.

20 minutes • Admission Ticket Free

Continue to one of the oldest and best wineries in Southampton, where you will enjoy complimentary wine tasting.

1 hour • Admission Ticket Included

Next stop is Sag Harbor, a quaint town with a unique atmosphere. Here, enjoy a tour of the harbor to view the yachts that are the toys of the rich. Then, stop to scour the antique stores and old-world shops for some bargains.

45 minutes • Admission Ticket Free