August 30-September 1      Sag Harbor, New York

Sag Harbor is renowned for its quaint New England architecture and its popularity with the rich and famous.  In the summer, its population swells with escaping New Yorkers who come there for the cool weather and the casual upscale ambiance.  Only a few miles from Southampton, another enclave of the socially prominent, wealthy, and/or entertainment megastars, Sag Harbor is a favorite docking place for those who wish to arrive in their yachts.  Although we had not been invited to any parties, we wanted to go there and experience the scene,

  After a lovely hour and a half cruise from Greenpoint, past the many beautiful homes and scenery of Shelter Island, we turned at the long breakwater into the crowded harbor.  Sag Harbor Yacht Club is a well-maintained, lovely marina with excellent dock help and located near the Main Street of the town.  Megayachts surrounded us.  It was similar to the boat show in Florida.  Some were even moored at the edge of the harbor.  We had never before seen huge yachts on mooring balls but apparently the demand was greater than the supply for adequate dockage.  The crowded marina was evidence that other boaters, like us, had swallowed hard and paid the exceptionally expensive rate (the most we had ever paid) to stay there.

As Labor Day was approaching, we were told numerous parties and events were planned to celebrate the last weekend of summer.  A Hilary Clinton fundraiser was scheduled in Southampton.  We should have had Stephanie and Amanda with us to help identify possible celebrities.  As avid People Magazine readers, they are more knowledgeable about this than we are and could have added excitement to the visit.

As a National Historic Site, the town of Sag Harbor has maintained its authenticity as a prosperous whaling and shipbuilding center during the nineteenth century.  The buildings have been transformed into modern enterprises but manage to retain much of their original exterior charm.  We spent hours perusing the many upscale shops and stores.  Small children, dogs, and very thin, tanned women in Lily Pulitzer sheath dresses were everywhere.  

 We enjoyed visiting the excellent bookstores and food shops.  We were well-stocked on the boat and did not go to any of the many restaurants (probably a mistake!).  On our final evening in Sag Harbor, we stopped at the historic American Hotel for a drink.  Our bar companion was a delightful young woman who teaches photography at the Ross School, a local prep school.  Later some of her other friends on the faculty joined us and we had a delightful conversation about the school and its students.  As a day and boarding school, Ross has a liberal arts-based curriculum but also offers sailing, equestrian activities, multi-media digital studies, and extensive overseas programs.  Tuition for these fortunate students ranges from $35,000 to $80,000 a year.  Recent fundraisers included concerts by Prince and Billy Joel. 

We were reluctant to leave Sag Harbor but Tropical Storm Hermine was threatening to bring high winds and waves to the area.  We wanted to cross Block Island Sound to Newport before the weather turned nasty.