Sarasota Sailing Squadron hosted the third event of the Viper Winter Series, drawing a competitive fleet and offering a mix of moderate breeze on Saturday and light, unstable conditions on Sunday. I joined Nick and Tobias for the weekend, continuing my week of winter sailing in Florida.

Saturday

The team rigged and launched early, sailing through the narrow channel and across Sarasota Bay to the course. Wind in the mid‑teens required de‑powering upwind, and I sailed in my cool weather ILCA gear – hiking pants, spray top and spray pants – which proved appropriate for the conditions. My position was the middle of the boat, responsible for hiking upwind, flying the spinnaker downwind, and in the later races I trimmed the main to keep the boat balanced through the chop.

Fending off another viper in the seconds before the start of race 1

Race 1 started with a bit of chaos. Another boat boxed us out at the committee boat, stalled and bumped into us. We had to shove them past just to get going, already a few lengths behind the fleet. The first beat was all about figuring out the boat and the conditions, and while clear air was hard to come by, we managed to pick off one boat by the finish.

Race 2 seeing the sailboats ahead of us already on the next leg.

In Race 2, the setup was better, but the short starting line and limited space made timing difficult, and we again started behind the group. Boat speed improved noticeably, especially downwind as we worked on linking waves and maintaining pressure. We finished ahead of two boats.

Vipers sailing downwind.

Race 3 produced the strongest performance of the day. A clean start allowed us to hold position with the fleet up the first beat, rounding the top mark in the mid‑fleet range. Despite losing a couple of positions later, we finished 8th and showed clear progress.

The moment Jon fell off the Viper

For Race 4, Nick offered me the helm. Approaching the line, I arrived slightly early and could not shed speed in time, resulting in an over‑early call and a return to restart. Shortly after, as the breeze built, I attempted to hike and discovered too late that my foot was under the bungee rather than the strap. I went overboard, breaking the tiller extension in the process. With the extension damaged and proper trim no longer possible, we knew our day was over. While Nick and Tobias got the boat back under control, I climbed aboard a nearby RIB and transferred back onto the viper for the sail in.

Sun setting behind a viper at Sarasota Sailing Squadron

Post‑race, we attended the debrief, secured a loaner tiller extension for Sunday, and wrapped up the day grilling dinner at our Airbnb and doing some film study of our sailing.

Sunday

With the boat already in the water, Sunday’s rigging was straightforward. The forecast called for light wind that would fade by midday, with a possible late sea breeze. After a brief postponement, the race committee started one race in marginal but sailable conditions.

Aboard a viper while being in the middle of the fleet with boats behind.

A solid start and a few early ducks positioned us on the side of the course we wanted, and clear air helped us round the first mark in 5th. As the race continued, some of the faster boats advanced, and the patchy pressure created opportunities and losses across the fleet. We finished 8th.

As the final boats finished, the wind shut off entirely. With Tobias needing to catch a flight and a long drive ahead for me, we had already agreed that any postponement would end our day. We sailed in while the fleet remained on the water. A sea breeze eventually developed, allowing additional races later in the afternoon.

We de‑rigged the boat, packed up, and I began the return trip to Richmond.

Thanks to Nick and Tobias for the opportunity to join them for the weekend. It was a valuable chance to learn the Viper, and extend my winter sailing break.

PICTURES | RESULTS | VIDEO

Tuesday

Following an off day between sailing where I worked remotely from an airbnb I arrived at Sarasota Sailing Squadron late last night.  Sarasota Sailing Squadron is on the point of an island jutting into a wide bay making it a great sailing venue.  There is plenty of beach launching and the sailing area is less than a mile from the launch.

The day started with a bit of a haze and no wind.  Temperatures in the low 70’s.  Even before the skippers’ meeting we were postponed ashore where we would wait for 1 1/2 hours.  The wind finally started to pick up, we went out and a race was started in 5-6 knots of breeze.  That ended up being the best of the breeze as it got very light during.  The wind was out of the South West and there was a little current from left to right at the bottom of the course.

I had a good start and focused on keeping a clear lane of wind and trying not to duck too many boats on port tack.  I did well on that first beat and rounded the first mark in 5th.  Downwind I lost one boat and on the 2nd upwind I didn’t stay in phase as well as I could have and lost a few more boats.  The final 3 legs of the race were pretty brutal.  It was a LONG race not moving very fast and the Radial fleet behind us wouldn’t finish in the time limited.  I ended up with a 12 in the 49-boat fleet.

After waiting for a little another race was started in a little bit more wind.  This time I started at the boat and had a good start on the front line.  I would sail almost to the left layline and was only crossed ahead by two boats.  At the top mark I was caught by a few boats on the right and was top 10 around the mark.  I continued to focus on clear air both up and down wind and held my position around the course as the 13th boat over the line – I would be 11th after OCS boats were taken into account.

By the 3rd race the wind had picked up a little more – now 8 and sometimes just over 10.  Where I could find pressure and make the boat go in light air – pretty much everyone could make the boat go in this wind and it would be a lot harder with the fleet clumped up a lot more around the course.  I had a good start, but got pinned to the left side and missed some shifts coming back the other way.  I was probably in the low 30s around the first mark.  Downwind I stayed in the middle of the course and was playing the shifts better to keep the boat moving fast towards the mark.  I picked off a few boats.  On the 2nd upwind I played the shifts and tried to keep my air clear and picked up some more places.  On the final run I gained a few and lost a few – again playing the middle of the course.  I finished 19th.

That put me in 12th overall – which sounds familiar as that’s how I finished the last regatta.  Back onshore we put boats away, cleaned up and there was a nice seafood dinner at the club.

Wednesday

In an about face in weather from the rest of the week – wind is what we got on Wednesday with winds in the upper teens and gusts into the lower twenties.  Slightly overcast skies with temperatures in the lower 70’s.  Having sailed in light air all week and most of 2016 – I wasn’t well prepared for these conditions.  My goal would be to just get around the course and salvage as much as I could.

In the first race I had an ok but not stellar start.  I made my way out to the right of the course and I moved the boat ok, but was a few rows back.  Towards the top it was clear the left was coming in better and I was in the back quarter around the top mark.  On the reach to the offset I lost my hand hold on the mainsheet and ended up capsizing to windward as what remained of the fleet sailed by.

I continued the race sailing conservative downwind to keep the boat under me and managed to pick off a few boats on the next two legs.  At the final jibe mark to the finish I messed up the timing of my duck and thwacked the boom on my head to add a little injury to insult.  I’d have a bruise for the next several days.

At that point it was clear I wasn’t competing and I decided to get home and save some time-off for later in the year.  And to finish it up – my dolly broke as I recovered the boat on the beach.  Thankfully the ride home was uneventful including an overnight stop in Florence SC.

EVENT WEBSITEPICTURES | RESULTS