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Top 30 Destinations by Personality Type
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Long Island, New York

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Personality Types that Like it Best

Did You Know … ?

  • Gatsby’s home in F. Scott Fitzgerald’s “The Great Gatsby” was inspired by Oheka Castle on Long Island.
  • Charles Lindbergh launched the world’s first solo transatlantic flight from Roosevelt Field on Long Island (1927).
  • The “horse head” scene in “The Godfather” (1972) was shot at the Falaise mansion on Long Island.
  • America’s oldest cattle ranch, at Montauk, dates from 1658.
  • The first ATM was installed in a Chemical Bank branch on Long Island in 1969.

‘Great Gatsby’ territory

Long Island is America’s largest island at 1,723 square miles, and it is long, measuring 118 miles — and 20 miles at its widest. It length lines up, southwest to northeast, roughly parallel to New York state and Connecticut. The island’s North Shore faces Long Island Sound with Connecticut on the other side, and the South Shore faces the Atlantic.

At its southwest end, it’s close enough to New York’s Manhattan and the mainland to be connected by bridges. Two of the city’s boroughs (Brooklyn and Queens) are on the part of the island near Manhattan.

The island has its own satellites, meaning Fire Island, a popular beach destination in the Atlantic, and Shelter Island at Long Island’s northeast tip, a quiet outpost for biking, hiking and kayaking. Both are accessed by ferry.

With its extensive shoreline and sandy beaches, Long Island attracts visitors for everything from sunbathing to surfing and saltwater fishing, plus the other amenities such destinations engender, such as galleries, museums, theater, dining and shopping. On Long Island, diversions include polo and horseracing, most famously the Belmont Stakes.

Many visitors come from the New York metro area, and some maintain second homes in beachside communities. In the late 19th/early 20th century, second homes on Long Island often meant mansions on large estates, located on the island’s North Shore, a section of which was known as the Gold Coast. President Theodore Roosevelt owned a Gold Coast home, Sagamore Hill National Historic Site.

Today’s visitors could plan an itinerary with Gold Coast mansions as a theme. At least two are hotels, but more are house museums. Three mansions are encompassed by the Sand’s Point Preserve. Some have new purposes, as a name like Suffolk County Vanderbilt Mansion, Museum and Planetarium makes clear. Others house the Nassau Parks Conservancy, a county museum, educational institutions and a Holocaust memorial.

The island also was touched by the American Revolution, which translates into another itinerary built around the tantalizingly named George Washington’s Spy Trail. In 1790, by then the president, Washington traveled to Long Island to thank supporters whose spying helped win the revolution.

Things to do for Venturers

  • Do you kayaking off Shelter Island. The island is good for biking and bird-watching, too.
  • Witness the famed Belmont Stakes at the Belmont Park racetrack in Elmont. Or watch polo matches at Bethpage State Park, staged June through mid-October. Another appealing option is the Hampton Classic Horse Show, held in late summer.
  • Take your surfboard to any of several ocean-facing beaches and catch the waves.
  • Build a personal itinerary around George Washington’s Spy Trail. The Stony Brook/Setauket area was at the heart of Revolutionary War spy activity on the island where the Culper Spy Ring was America’s first covert group.
  • Don the gear for fascinating dives along Long Island’s coast, dubbed Shipwreck Alley for the significant number of ships to go down in its waters. In any case, choose the North Shore for calmer dives, or tackle the South Shore (the Atlantic) for something more challenging.
  • Build an itinerary around aviation that includes the island’s Cradle of Aviation and American Airpower museums, plus the Bayport Aerodrome for vintage aircraft. Include some time in the sky, soaring in a glider.

Things to do for Centrics

  • Go to sea on a seal and whale watching excursion. Or, in winter, join a seal watching walk at Montauk Point State Park.
  • Charter a boat for deep-sea fishing out of Bay Shore, Freeport, Greenport or Montauk among others. Or, try the surf fishing at Montauk Point.
  • Ride horseback on the beach at Deep Hollow, America’s oldest working cattle ranch. Take a guided tour of the ranch, too.
  • Get more than a glimpse of Long Island’s seafaring past at the Cold Spring Harbor Whaling Museum. And/or pursue the same at Sag Harbor Whaling Museum, housed in an 1845 whaler’s mansion.
  • Visit at least one of the three Long Island lighthouses open for tours. At any of them — Fire Island Lighthouse, Horton Point or Montauk Point Lighthouse — climb to the top for the view.
  • Create your own wine itinerary taking advantage of winery-sponsored events such as a wine festival or wine pairing dinner. Or, attend the autumn Oyster Bay Oyster Festival.

Things to do for Authentics

  • Overnight in one of the mansions built when part of Long Island’s North Shore was known as the Gold Coast. The Glen Cove Mansion and Oheka Castle fill the bill. Or, at least tour the Oheka Castle.
  • Go to the beach. East Hampton’s Main Beach and Southampton’s Cooper’s Beach are among the most highly rated.
  • Play golf on the Black Course at Bethpage State Park, twice the site of the U.S. Open.
  • Accomplish two goals in one place. Attend a concert at Old Westbury Gardens, a Gold Coast estate in Old Westbury. Tour the gardens and historic mansion.
  • Join a guided tour of the Pollock-Krasner House in East Hampton, the home of Abstract Expressionist artist Jackson Pollock.
  • Look for a lunch or dinner cruise, or other sightseeing on the Long Island coast. Cruise departure points include Bayshore, Freeport and Port Jefferson.

Additional Resources

For more information, consult the Long Island Convention and Visitors Bureau and Sports Commission at