DayCations from Sachem: Sag Harbor

Success generates a unique optimistic high that broadens a person's horizons.  When an entire community achieves this level, then that place is a wonderful destination for a DayCation. 

Sag Harbor is one of these special places, for in the harbor lies dozens of super yachts and the main street is lined with a New England collection of boutiques, hardware stores, fine restaurants, bars and even an old time movie theater.  By car you have to weave your way north from the Hamptons. 

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The roads grow more narrow, but the traffic more bearable and the homes more elegant, majestic and historic.  Sag Harbor was a whaling town and the sea captains grew rich and built distinctive, terraced homes.   Some of these now house museums, others are privately owned, sometimes open for display.  A few are amazing stores filled with nautical treasures, the work of local artists or fine ladies clothing. 

When heading towards Montauk Point, Route 27 will bring you into the center of Bridgehampton, a wonderful town to visit if your style is more elegant and ritzy.  By making a left, going north on Bridgehampton Sag Harbor Turnpike you will travel about five miles before you come to the center of Sag. 

Arriving in Sag Harbor by boat is even more memorable.  Before entering the rock jetties, you cruise along the backyards of several beautiful waterfront homes and estates.  Jimmy Buffet's mansion features a long dock, designed to handle any of his fleet of seaplanes, which includes the historic 1939 Grumman Albatross named the Grey Goose.  

The main channel is through a mooring ground.  It seems like you are cruising through a  forest of masts, for the sailing vessels are beautiful, some huge, glistening and sleek.  Just as you approach the long wharf and town dock, to the east is a row of mega yachts and floating palaces.  Most are over hundred feet long, some three or four stories tall. 

The eastern shoreline along Bay Street, near Division Street and Main, offer the visiting sailor every type of store, bar, restaurant,  delicious pizza, ice cream or burger. Several galleries and thrift stores hold treasures from the world and imaginative creations from local artists. 

The harbormaster oversees the marina and their showers and restrooms.  His office is on Bay Street, above the public restrooms.  The bathrooms were clean, the showers hot and the location of the Sag Harbor town dock puts you in the center of Sag Harbor life.

The intersection of Route 114 and Main Street offers a glimpse at what a DayCation to Sag Harbor offers.  The Bay Street Theater offers original and plays, vintage movies, nationally known standup, multicultural presentations, classes and pretty good drinks.  Across the street is a pub with meals, drinks and an atmosphere of relaxed rowdiness.  A strip of stores from a Frank Capra film line the west side of the street.  A grocery store, a 50's drug and department store, book shop, a very nautical antique shop, an old restored movie theater share the main street with city chic coffee shops, a surfing stores, several cafes and jewelry shops.

 The east side is even more interesting with the American Hotel in the center of the block.  This historic building has a "Great Gatsby" feel to it, with a brass and dark wood bar, cozy dining rooms and sidewalk seating.  Nearby are two Asian restaurants, these are this season’s “place-to-be seen spots.”  Weekend evenings they buzz with electricity until well after midnight.  Yet down the block on either end of the street are pizza parlors and ice cream shops that offer a more blue collar experience and delicious food.

But the beauty of the East End can best be seen aboard the American Beauty II. This is a 44-foot tour boat designed for both ecological and sunset cruises. Captain Don Heckman leaves three times a day from Long Wharf, at the traffic circle in the middle of Sag Harbor.   His boat is available for private charter, fireworks cruises and children's parties.

 "My favorite spot is Mashomack Nature Preserve. It is a hot spot for all types of birds, osprey and wildlife. It is just beautiful," he said.

His tour of the harbor, Barcelona Point, the Cedar Point Lighthouse and around Shelter Island is always filled with surprises. "I saw a deer and her doe swimming across to Shelter Island the other day. And once we spotted a porpoise caught in a net by the shore. It was a young one, sort of a 'stupid teenager,' who was so involved chasing some food he got caught up and stranded for a bit. We called the Riverhead Foundation (a local organization that provides animal rescue and rehabilitation) but we just waited a while for the tide to turn and he freed himself." 

 A DayCation to Sag Harbor illustrates almost all of the sides of the East End.   There is glamour, history, fine food, unique shopping, amazing nightlife and a stroll through a quaint little town.  Take the ride one morning.  Make it early to not only beat the traffic but to enjoy as much as you can, for there is so much to do, see, buy, eat and treasure.

Distance from Sachem: 52 miles, or roughly a 1:15 drive