Sailing

All posts related to Sailing on Guest of a Guest for Sailing.

Inspired by Don Draper's advertising genius and a love for all things vintage, we've tracked down some popular advertisements from yesteryear to get you in the spirit of summer. Although these dated ads are fun to flip through, we'll leave it up to you to decide whether you want to take any of their advice. More»

  • You may not be able to sidewalk shop in Montauk any longer, but have no fear, now you can eat outdoors thanks to recent legislation by Southampton officials. Sidewalk outdoor dining is here to stay [East Hampton Star]
  • Love sailing the Hampton's waters but the prospect of purchasing your own sailboat is dismal. Don't worry because Cory Abad has already thought of that for you with his The Hampton Boat Club [Curbed]

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oyster bay waterfront

My town has its own little lake, and in the summer most kids either join the swim team or take sailing lessons. As I'd done the former, yesterday's sailing excursion out of Oyster Bay consisted of my mother manning the jib and my boyfriend, the tiller and main sail whilst I relaxed(ish, the water was rawther choppy) and soaked in the views. At Oyster Bay's Waterfront Center, you can rent a variety of sailboats, and we chose the Rhodes 19, which comfortably held three, and might have squeezed four. So long as one sailor has an ASA certification, you can rent a boat for either the morning (8-12) or afternoon (1-5), and each session is $90. More»

arboretum in oyster bay

By Leonie Glen
While visiting my brother's family in Quogue, my daughter would often ask why my family didn’t spend our summers out there. After all, we grew up on L.I., and we had cousins in East Hampton with a mouth-watering property and a long-time membership at the Maidstone. What were we thinking?

Well, we lived on the North Shore, and the Tri-harbor area (Oyster Bay, Cold Spring Harbor, and Lloyd Harbor/Huntington Bay) remains a place no one would want to leave in the summer. What it lacks in surfable splendor, it more than makes up for in charm, sailing -- both competitive and desultory -- and a hilly, crenellated shoreline that F. Scott Fitzgerald immortalized in The Great Gatsby. Horseshoe crabs hug the sea grass, clams lurk in the mud, and starfish cling to dock pilings. There are also a couple of outstanding golf courses (the best is at The Creek Club), but they are NOT open to the public!

What follows is an introductory itinerary, one which starts in Oyster Bay, home of Teddy Roosevelt. More»