Shields at the Topmark              


Bill Simon 
Oakcliff Sailing Center 


Wednesday May 18, 2016 from 5:30 PM to 10:00 PM EDT

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Oakcliff Sailing Center 
4 South Street
Oyster Bay, NY 11771

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Wednesday Night Racing
Presented by Dream Yacht Charter

Dream Yacht Charter  

Fleet racing with coaching from Oakcliff Staff

Oakcliff Sailing has partnered with Dream Yacht Charter to offer weekly racing throughout the spring, summer, and fall on Oyster Bay, New York. Sailors who participate in the racing will receive discounts on charters all across the globe.

 The Wednesday Night Series presented by Dream Yacht Charter will begin May 4, 2016 and carry on every Wednesday through the summer. Sailors will race on Oakcliff’s fleet of 40 foot keelboats with onboard coaching from Oakcliff staff including America’s Cup winner and two time Whitbread around the world racer Dawn Riley. 

Sailors who participate in at least five of the Wednesday Night Series will receive a 5% discount on charters. Those who attend at least ten times will receive a 10% discount.

Racing will include coaching before, during, and after the race. The series is open to any Oakcliff supporters.

Begin with a pre-brief at Oakcliff at 5:30, race, and then enjoy a relaxing debrief and beverege at Sagamore YC. Throughout the season we will talk about pre-race preparation, starting, course management, boat handling, sail trim, strategy, tactics, crew training or in short, everything to do with sail boat racing. The evening generally concludes just after sundown.

Put together your own team of supporters or sign up individually and be a part of a pickup team for the night, but please remember to bring your sunscreen, reusable water bottle, sunglasses (with a retaining strap) and a life jacket. If you don't own a life jacket, you may borrow one from Oakcliff.

To claim your Dream Yacht Charter discounts you must register and sail.  Those who qualify can request a code from


2016 Sailing Instructions

All participants must read and adhere to the Oakcliff Sailing Center Safety Rules and Regulations.  Please click this link:

If you are new to Oakcliff this is a great way to get your feet wet. Register by clicking the button below.