December 28, 2016: Day One of Sailing 101

Boat: Chomsky, Catalina 22
Location: Sarasota Bay, Sarasota, FL
Sailing Course: ASA 101, Basic Keelboat Sailing
Wind: light in AM; 7-10 knots in afternoon.

view-from-sara-bay-sailingFirst day of sailing 101, with Captain Bill of Sara-Bay Sailing. We arrived to the dock at 9:30 am, and went up to the office to work on land instruction for an hour or so. There was no wind in the morning, and after tying knots in the office, we departed under power in a Catalina 22. In the channel we saw a manatee — a sign of how warm it’s been since they are usually long gone for warmer waters by this time of year — along with a couple of dolphins feeding in the shallows. We puttered over to a boat at anchor — friends of Captain Bill’s who he claimed hung out with Jack Kerouak — and yelled across the water to chit-chat for a bit before heading out to the bay.

The morning on Sarasota Bay was still, hot, and calm. We saw a loon on the glassy water of the bay, then heard it call a little while later. Bill talked a bit about how to read clouds to find wind (clouds indicate temperature differentials which create wind as hot air rises and new air rushes in to fill the void), we practiced with the tiller under power, and finally, after motoring across the entire bay, we puttered into a dockside restaurant called The Bearded Clam for lunch. It’s almost as appetizing a name as Crabby Dicks. Who thinks these names are funny for a place to eat food is beyond me. This was probably around noon. The wind began to pick up while we ate our fish sandwiches, and around 2pm we got back out on the bay and sailed.

I hoisted the main and we practiced tacking. It was easy compared to our little 13′ yawl. The larger size of the Chomsky made it much more forgiving – each tiny movement didn’t make the boat lurch or heel. I tacked several times as the helmsman, then we practiced jibing. Winds were maybe 7-10 knots, enough to create a chop. I was nervous about jibing — the boom was large and heavy — and I found holding the tiller on my knees to be awkward while trying to sheet in the main. I didn’t sheet it fast enough on most of my attempts, but I did do a good job of letting the sheet swing behind me without getting entangled, of avoiding the boom as it swung across, and of uncleating the main when it was time to release it as the stern crossed the wind.

After jibing, Brian helped unfurl the jib and we practiced tacking as crew. I held the helm for a few tacks while Brian crewed, and then we switched so that I could crew.

Because of the no-wind morning, we stayed out on the bay long past the designated end time of 4pm. When we approached the channel, Brian furled the jib and and lowered the main while I fed the halyard. We motored in under a pink and orange sunset. Captain Bill docked the boat and we handled the lines.

Pronunciation (and spelling)

  • Leeward = loo-ard
  • Lee = loo
  • Gunwhale = gunnel
  • Winch is spelled with an “i” 😂


  • To determine the tack, look at the boom. If the boom is to port, you are on a starboard tack.


Tacking as helmsman. Sailing on a close haul, sitting on the windward side.

  • Call “Ready About.”
  • Crew prepares for the tack and then says “Ready.”
  • Check for boats and hazards.
  • Call “Helms-a-lee,” push the tiller to lee and commit to the turn — push it all the way across to the seat opposite and hold it.
  • When the boat flattens (stops heeling) and/or the boom swings across the centerline, hold the turn and switch your body to the windward side of the boat.
  • Watch the sail. When it fills (stops luffing), stop the turn, check the horizon for a mark, and hold the course.

Jibing as helmsman. From a broad reach, sitting to windward.

  • Remember that to go up the wind, steer the bow away from the mainsail. Heading up keeps from accidental jibing.
  • When ready to jibe, call “Prepare to jibe.”
  • Crew gets ready then says “Ready.”
  • Call “Jibe-Ho!” and pull the tiller onto knees to go downwind (full run then through to other side) and start sheeting immediately and very fast. Drop line at feet, not across your legs — it will burn when released at the end if it runs across your legs.
  • Let the boom swing over on its own, release the mainsheet, let go of the sheet and let it run out.
  • Stop the turn when the sail fills and the boat is on a broad reach again. Look at the horizon for a mark and hold that course.
  • When everything is settled, switch body to windward side of the boat.

Tacking as crew. Sitting on same side of boat as helmsman.

  • Reset the lazy jibsheet with 2 wraps clockwise around the winch if it’s not already set.
  • Helmsman says “Ready About.?”
  • Pinch lines wrapped around working winch and uncleat the working sheet.
  • Tug the lazy sheet to make sure it’s wrapped on the winch in the correct direction.
  • Say “Ready” to helmsman.
  • Helmsman says “Helms-a-lee” and begins the tack.
  • Release the (former) working sheet from the winch — unwrap it and let it fly.
  • As boat levels, move across the boat with the helmsman.
  • Haul the new working sheet to pull the jib across (if it didn’t cross on its own) and trim the jib.
  • When everything is settled and tack is complete, pinch the line on the working winch and cleat the working sheet.
  • Reset the lazy sheet by wrapping two times clockwise around the winch.

Author: Andrea Badgley

Writer at Butterfly Mind and Andrea Reads America. Happiness Engineer with Automattic.

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