Stingray Point Regatta

Trip dates: 
Thursday, August 28, 2025 to Monday, September 1, 2025
Trip length: 
5 days
Type of watercraft: 
Sail
  • The delivery crew
  • Inspecting sail trim
  • Headed out for battle on Day 2
  • Squirreling the kite
  • Last day crew
  • Pushing hard upwind

Instead of dragging the Olson all the way down to Deltaville, Dewey and I made arrangements to race with Frank and the gang on team Whirlaway for the Stingray Point Regatta this year. We packed up the boat early Thursday morning, and set off in pleasant, moderate conditions for the trip south. We put up the #1 when we got on the Bay, and power reached for a bit until the wind built into the high teens. We geared down to the #3, for the first time it had ever been up, and enjoyed a pleasant couple hours of sailing. About when we got to Smith Point the wind shifted on the nose and started building, and we spent the rest of the trip having a rather wet motor. All along the way Susan prepared delicious snacks. We landed around dinnertime and enjoyed a great first night of camping.

Day 1, the Stingray Light Race, provided shifty, variable conditions. We got off a clean start on a reach, and I coached very active trim on the headsail to keep us ahead of our competition. We worked our way through strange shifts, and managed good performance on the upwind leg. We rounded the first mark, popped a spinnaker, and sailed a great kite run to the next mark. We gybed around and kept good performance for the remainder of the race, finishing second of four boats.

Day 2 delivered breeze in spades, with sustained high teens gusting to 20, and far bigger wave state than we typically see in Solomons. We raced three races and pushed the boat hard, but had lots of problems with the spinnaker in the first couple races. Dewey and I put in lots of good work on sets, gybes, and douses, but it was a real struggle. The wind lightened up a bit for the third race, and we were able to fly a spinnaker with more confidence. We ended the day in third.

Day 3 was a bit more tame, and offered great sailing conditions. We were the sharpest we'd been all weekend, and with the exception of some unexpected halyard trouble we sailed clean races with tight spinnaker work. We were much more in the mix than yesterday, but still couldn't climb out of third for the day. We ended the regatta third in class overall.

We packed up the boat and headed north first thing in the morning. We started on a rather heavy close reach, which gave way to light conditions by lunchtime. We motored for a couple hours, and eventually went back to sailing for the remainder of the trip home. 

As always, the regatta was a fantastic weekend of hard sailing, great parties, warm hospitality, and a fun time by all! This event is one of the highlights of my sailing year each year.