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DEC 9-13, 2016
Islamorada, FL

(Click Here to Register for the Race)

Rules and Information


This race is put on by all of us -- the competitors, their crew and ground crew:

  • There is no Race Committee.
  • Your ground crew is required to help in any way possible (i.e., scoring, timing, starting, etc.)
  • There is no Race Management, which is why this race is so inexpensive - $40 entry fee. (Plus additional fee for the Upper Keys Sailing Club.
  • There is no Protest Committee, so please obey the racing rules and rules of the road.
  • There are no chase boats, so please be prepared to fend for yourself. (See Stories from 13th year)
  • You will be rewarded for assisting a boat in trouble (keep track of your time in doing so).
  • You may paddle at anytime.
  • There must be at LEAST two people on the boat
  • Registration 3-4 PM on Friday and 7:30 AM on Saturday, with a skippers meeting at 8 AM at Islander Watersport.
  • Feel free to ask questions of veteran sailors about the course and about safety. You will still need to do final registration, pay the fees, sign the waivers, etc.,


The venue will be Starting and Finishing at the Islander Resort, with a stop at The Upper Keys Sailing Club in Key Largo

To attempt this race, you must be competent, able sailors, knowing how to do such things as:

  • right your own boat
  • read navigational charts
  • read the water color for shoals
  • anchor your boat in case of heading for a peril
  • ride out squalls and storms
  • You must wear an approved PFD, have all USCG safety equipment aboard, a waterproof chart, waterproof flashlight, and adequate anchor and line.
  • Both skipper and crews must write the emergency telephone number on their arm (waterproof pens will be available) --
  • 305-433-0845, or 305-433-0840 -- these are cellular telephones that will be manned all the time but can be unreliable at some sites in the Keys. If you are retiring from the race or broken down, you must call these numbers right away. Otherwise, we might be sending the USCG after you.
  • don't forget to take essentials like water, sunblock, and food.

The Course

  • On the first day, There will be a LeManz Start off the beach of the Islander Resort Pier. (Positions for the start will be drawn ) The course goes northerly up Hawk Channel to Angelfish Creek, then southerly through Card Sound and Barnes Sound.
  • The finish will be at Upper Keys Sailing Club and the line will be between a orange flag on UKSC Pier and the main mast of a cruising monohull sailboat with a green sail cover that is more or less permanently moored about 100 feet off the UKSC Pier. You may finish in either direction.
  • Late Finishers: If you are more than two hours after the first boat finishes, note the time you finished and give that info to score keeper. You may call the numbers listed above to do so.
  • On the second day, there will be a deep water start between an orange flag and the main mast of a cruising monohull sailboat with a green sail cover that is more or less permanently moored about 100 feet off the UKSC Pier.You must cross between the two, leaving the moored boat to starboard. From there the course goes southwesterly to Channel Five Bridge, then northeasterly up Hawk Channel to a finish line at the Island Resort. The Finish Line is between an Orange Flag on the Islander Resort Pier and an Orange Mark. You may cross in either direction.

Starting Sequences

  • Rule 26 Start Procedure will be used. A warning sound may be used one minute before the sequence start as a courtesy to get your timing device ready. A Red Class Flag will go up with a sound a 5 minutes before the start. A Prep Flag will go up with a sound 4 minutes before the start. The prep flag will come down with one minute before the start, and the Red Class Flag will lower with a sound at the Start

Do NOT be over early at the start!!

  • If anyone is over early, the individual recall flag will be flown for four minutes or until the over-early boats have exonerated themselves by restarting, whichever comes first. Over-early boats will NOT be notified. If a boat is over early and does not re-start, that boat will be assessed a 10% time penalty for the day. If there is a general recall, the general recall flag will be flown, the clock will continue to run, and the fleet will restart exactly five minutes later. However, all of the above is really moot, because the Race Starters absolutely forbid anyone to be over early.

Portsmouth Numbers

  • US Sailing D-PN numbers and mandatory modifications will apply for the entire race, and all sails and modifications must be claimed by 0800 Saturday morning.
  • The modified D-PN number will apply regardless of whether or not the additional sails and rigging are carried on the boat.
  • The Optional Modification for crew weight, and for spinnakers in a distance race will NOT be applied.


  • The dilapidated but highly coveted and esteemed Olde Lawnchair with the record of all past Steeplechases goes to the first boat overall on elapsed time. And the Carlton Tucker Perpetual is kept here in Key Largo.
  • A perpetual trophy is taken home by the overall Portsmouth winner.
  • Keeper trophies go to both skipper and crew of first, second and third place boats on Portsmouth and to the overall winner on elapsed time.
  • All finishers will be awarded a bottle of champagne

Motels in The Keys:
(It is highly suggested you stay at the Islander Resort -- perhaps you can even make arrangements to leave your boat there for the Tradewinds in January)

Parts, Equipment and Gear

  • If you are getting parts and equipment before you get to the event, you can order them through and have them shipped to you % Rick White, 6 Coral Way (mm105), Key Largo, FL 33037
  • West Marine is located in the Pink Plaza about 1/2 mile south of Rick's Place on the Bay Side, just past Marvin Adams Waterway Cut. They are open 0800 to 2000 every day, except Sunday, and then from 0900 to 1700.

For more information contact:

  • Rick White, PO Box 2060, Key Largo, FL 33037, Tel 305-451-3287, Fax 305-453-0255, e-mail

Click Here for PreRegistration

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