Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you're on a federal government site.


The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

United States Department of Transportation United States Department of Transportation

Varsity Offshore Sailing Team

2015 Around Long Island Regatta

The Around Long Island Regatta is 190 mile annual regatta cohosted by Sea Cliff YC and Sheepshead Bay YC.  This year’s race started off of Sheepshead Bay on Thursday July 30th at 1500.  Montauk Point Light House and Orient Point Light House are the only two marks on the course and both must be left to port.

We experienced just about every type of condition Mother Nature could come up with.  At the start we had rain, large waves and southerly winds gusting between 25-30kts.  It made for a wet and exciting start!  Not long after the start we were overrun by a very intimidating looking cold front which brought more rain and lightning.  Fortunately it turned out to be not as bad as it looked.

The breeze moderated throughout the night and slowly started to clock.  This enabled us to initially reach with our A3 Spinnaker and eventually peel to our A2 running spinnaker.  Not before a couple of spectacular wipe outs!

We rounded Montauk Point close to dawn and by that time the breeze had completely clocked around to the North West.  Dawn also produced very thick fog.  Upon entering Long Island Sound the fog burned off and we were left with sunshine and about 10kts of breeze from the North West (much better than I expected!).

We spent the first part of the day beating down the Connecticut shore line before making the decision to cross the sound and work our way down the north shore of LI.  We stayed as close to shore as we dared in an effort to gain current relief.

With about 15 miles to go and close to sunset we were given classic LI Sound in the summer.  No wind!  However we did have a favorable tide and worked very hard to keep the boat moving. Managed to finish just before midnight Friday night.

We had no idea how we had done overall at that point.  Our three big mistakes or incidents during the race cost us quite a bit of time.  The first was being slow to go to a kite early in the race (maybe being a little overly prudent in the cold front).  We definitely lost miles due to the decision.  The second was our spectacular wipe out during our spinnaker peal.  The A3 went where kites go to die! Under the boat!  Somehow we managed not to kill it, but this cost us about 30 minutes.  Finally after having caught up to the lead boat at Montauk we made the decision due to the fog and fatigue that we didn’t want to beat through Plumb Gut.  The weather routing also suggested that we might not need to anyway.  In the end what was a prudent call probably wasn’t the best tactical call.

However, we did enough other parts of the race well and managed come away with a great overall result.  3rd in Class, 4th overall (out of 25), top service academy (beat both Navy boats) and tied for 2nd overall in the three boat team competition.

It was a race of great varieties that proved to be very challenging.

Next up for the S/V Orbit and the offshore team is the Vineyard Race.  Friday September 4th we will start off of Stamford CT racing east to the exit of the sound on our way to the Buzzards Bay Tower (just off the western coast of Martha’s Vineyard).  Round the tower and then it’s back to Stamford for the finish.  243 nautical miles.



L-R Stephen Webster '18, Scott Johnston '18, Charles Lomax '18, Max Neubelt '17, James Noel '18, Karl Wallin '18

Last updated: Wednesday, August 12th, 2015

Now Accepting Applications for the Class of 2024

Learn more about the requirements and expectations of Midshipmen.