Originally posted to Patreon March 21, 2026.
Well, it took a while, but our friend, patron and raffle winner Tal and I finally connected for the “win a day sail aboard Jacie Sails” prize from our last online party.
(Side note: It’s about time for another party!)
Tal escaped a winter storm just in time to land in Tampa for…a winter storm. The “Storm Down South” didn’t involve snow, though…just a northerly wind, and a lot of it.
I originally figured we’d just go to dinner on arrival day (Sunday), but given the daylight savings and all, we decided to take a quick sail in Boca Ciega Bay.
In what would become a theme of the week, we did not use the jib, but had enough south breeze to rely on the main.
Sunday would be the last full day of southerly breezes, though, as a strong northerly front came in midday Monday, dropping the temperature a good twenty degrees.
Small Craft Warning
Originally the forecast for Monday looked like a complete no-go with thunderstorms; but we ended up with a window of sorts Monday morning, and I figured we could at least get Tal out into the Gulf.
So we motored down Pass-a-Grill against an opposing current and a now very potent remnant of the south wind, making just over 4 knots.
With the wind sustained at 22 knots and gusting to 30—and starting to feel a significant chop as we neared the entrance—we decided that a view of the Gulf would be plenty sufficient. So we motored back up Pass-a-Grill, now making seven knots over the ground.
Winches. Am I right?
The predicted front and thunderstorms did indeed arrive Monday afternoon, so we decided to attack the frozen winches, starting with the starboard one.
(Here is the resulting How Not To Sail Minute podcast. If you don’t have the daily micropodcast in your bag yet, you can get it here: https://hownottosail.com/minute , or wherever you get your favorite pods.)
To make a long and frustrating story short, we managed to get the topmost fifteen individual pieces of each winch removed, but no amount of PB Blaster, twisting with a band wrench, tapping upward with a rubber mallet or cursing would coax the drums off so we could get to the innards and lubricate them.
The Real Deal
So we had no jib sheet winches, but now we had a stout northerly breeze. And we decided to make the most of Tal’s last full day…by going out in the second straight day of a Small Craft Warning.
As it turned out, what’s left of my mains’l (the leech was, and is, still ripped a little) was plenty to get us a nice 25-mile sail in 20+ knot wind.
In the time it had taken me to babble a couple of paragraphs about something, we were suddenly in just over five feet of water. And what does my vessel draw? 5’2″. Unloaded.
I decided not to sail downwind in Skyway Channel, since the tide was still a bit low. There is some shoaling where the ICW there exits into Tampa Bay, and I didn’t want to go aground with a fresh breeze pushing me. I figured we’d motor back up that channel later on a rising tide, which should be a much better plan…right?
So instead, we had a fine beam reach east under the Meisner bridge (I-275) into Tampa Bay, and then turned southwest to get Tal a nice “up close and personal” photo-op with the Skyway Bridge.
This we managed to do without mishap…and we also beat a container ship through the bridge by several minutes. (We loitered around just north of the shipping channel to get a photo of that, and to douse the main in what were now sloppy conditions.)
Taking a Bottom Sample
Under motor again, we took it very slow up through markers 2 and 3, and once clear of those, I breathed a little easier…
…but perhaps I shouldn’t have.
There we were, maybe a half mile north of the channel entrance, in a good 15 feet of water…when we had that “rapid unscheduled deceleration” we sailors dislike so much.
In the time it had taken me to babble a couple of paragraphs about something, we were suddenly in just over five feet of water. And what does my vessel draw? 5’2″. Unloaded.
(Another audio clip…)
Thankfully, we were able to extricate ourselves (I’m not even sure I backed down in this case, but might have just plowed forward) and were soon in 18 feet again…but Tal said the tone in my voice when we did a nose-wheelie was a bit concerning.
It was pretty weird. We were dead center of the channel in an area where there wasn’t even any shoaling nearby on the chart…but there it was. So just a note, if you’re in Skyway Channel there, near where the kite surfers are…be on the alert for a sudden change in depth!
What Are the Odds?
Irregardless, as Our Friend Bill would say, I believe a large time was had by all. We turned a “Daysail aboard Jacie Sails” into multiple sails and motorings and whatnot, with a few good dolphin sightings thrown in for good measure.
Just to put a bow on the title of this post, though…I should explain how “What are the odds?” became our catchphrase for the trip:
As Tal and I were headed to West Marine, we passed (or were passed by) a Tesla Cybertruck. The usual…stainless color.
As we waited to pull out of the West Marine parking lot onto the street, a Tesla Cybertruck came down the street, passing right in front of us.
“Do you think that’s the same one?” I asked Tal.
“Gotta be. I mean, what are the odds of two of them in the same area like that?”
At that moment, a second identical Cybertruck came along, not a hundred yards behind the first one.
So now, as Paul Harvey would say, you know the rest of the story…
…almost.
As I left for home a couple of days after Tal’s departure, crossing the Howard Frankland bridge, I passed a transport truck carrying…
Yep. You guessed it.
What are the odds?
—
Special thanks to Tal for his patience in scheduling this adventure, for his good humor, and especially for returning the shampoo bottle nozzle to the closed position.
