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Day Sail Rally

June 1

June 1 All day

Signup Here!

Arrival: As early as 9 am on Saturday morning. 


  • Public Dock in front of Rock the Dock
  • 100’ of space in front of the Seaport

Optional Coast Guard Safety Check

  • Why do it? Confirms the safety of your boat, potential for discount on boat insurance, points toward winning event for doing it, more points if you pass.
  • You need: boat, registration. Attached is the check sheet they use. Not intended to be a surprise; idea is to pass it.
  • It takes 45 minutes to complete. No appointments after 10:15 am so that everyone can attend the meeting. 

Before the race starts:

  • Find some crew: choose a few people off the dock who aren’t boat owners to go with you
  • Complete the “knots” challenge. Random person (dice roll) chosen from crew. Random knot (dice roll) needs to be tied by the selected person.
  • Buy in for poker ($5 minimum)
  • Get the packet of trivia questions

Skippers meeting at 11. 

  • 3 hour time limit.
  • Course marks determined by the trivia questions (3 sets)
  • No touching marks
  • No starting line- leave the dock anytime after the whistle/skippers meeting
  • 15 minutes of motoring time “free”. Deductions for motoring after 15 minutes. Skipper responsible for monitoring time.
  • Take a picture as you pass the mark to your stern – literal closeness doesn’t matter, but you do have to pass it. (3 marks). Distance for pictures is fine
  • Everyone in a PFD the whole race


Earn Points:

  • Do the knot successfully
  • Do a Coast Guard Safety Check
  • Pass Coast Guard Safety Check
  • Round all the course marks
  • Answer trivia questions
  • Photograph scavenger hunt items
  • Place returning to the dock (most points for fastest back)

Lose Points:

  • More than 15 minutes of motoring
  • Opening the wrong envelope from the scavenger hunt
  • Send in the trivia questions before rounding the mark proof
  • Crew without PFDs

Awards Ceremony at 3 pm on the dock by Rock the Dock

Awards: (winners can choose from what’s available)

  • Gift card to West Marine
  • Wine
  • Liquor

To bring:


  • Boat, registration, Coast Guard paperwork


  • Phone with camera
  • PFD
  • Snacks, water, etc
  • $5 for poker (optional)

This event is open to anyone! Please join us at Rock the Dock to start. So what is a Cruising Day Sail Rally? It is NOT a race! The entire day is based on many varying challenges, and points are awarded accordingly.

Here’s how it starts:

You have to show up to the meeting location for the first challenge, which starts with a safety inspection for which you get points based on having all of your safety gear and appropriate burgees and flags flying.
Then, a randomly selected crew member is tasked with tying a knot or two (also selected at random). I hope you brought some seasoned crew with you! If not, it’s ok, as this is only a couple of points.

Next, we host a skipper’s meeting to go over all the rules and tasks for the day.

Points on the water are generally gained by following all of the clues and instructions, answering nautical-themed trivia questions, and always making sure tasks are completed in order. The course is unknown by any of the boats until you open your first clue.

Here’s the central premise of the on-the-water game:

Each skipper is given a packet for the day, containing several envelopes for each of the clues.
Envelopes for the clues include either the right answer, a course heading, and a standard playing card (for the best poker hand at the end of the day); or if you got it wrong, you’ll know.

Each correct answer gives you a point, each incorrectly opened envelope means you don’t get that point. Using the correct envelope, it is time to set off.

Submit your answers and scores before rounding the buoy for your points to count!
You’d better have your sails ready to go, because an extra point goes to those that use less than a set amount of motoring time.

While you are out, spotting wildlife and posting to the club’s facebook page gets you additional points.
Once you reach the destination of your first clue, you usually round a buoy with some sort of distinguishing mark that helps you determine the answer to the next clue. Get it right, and you’ll know your next course heading.

Your nautical-themed trivia answers and total leg score needs to be submitted to (via a photo to the organizer with a crew member in the shot) before rounding the mark. If you don’t, your trivia points don’t count for that leg of the course.

The rules can get a little confusing’ But that is the point. This event keeps you and your crew engaged the entire time ‘ whether the crew are completing trivia, helping sail towards the next mark, watching for wildlife, or making delicious snacks and beverages!

Signup Here!


June 1
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CYCT Cruising