Day 1 of our trip to Toronto Island takes us from Cobourg to Port Whitby Marina on a beautiful sailing day and Lori begins her sailboat racing career.

Today is the first day of our Toronto Island trip! Everyone is pretty excited, we’ve never been to Toronto Island before and heard lots of great things about it. Although we are a bit nervous about the rules and boat traffic in the harbour!

Here is our rough shopping list for the trip. Our latest favourite food to bring is 7-layer dip.We just grill some chicken on the BBQ, chop it up and a few minutes later we have burritos. 

Our trip plan from Cobourg to Port Whitby Marina was pretty straight forward, just head West for 35 nautical miles while making sure we head South enough to miss Peters Rock. 

We left Cobourg at a reasonable hour, 8:30am. Weather was looking good, even though there was a storm moving in slowly from the North East but we should stay ahead of it. Most of us were up and ready to go, but one of us prefers to stay out of the way and sleep. 

As we were leaving the harbour, I didn’t realize that one of the boats anchored was leaving. It was motoring forward towards us while pulling up their anchor (I admit, I’m a bit jealous of boats with a motorized windlass). We picked up speed to stay out of their way and exited the harbour right in front of them. Of course, once we were out on Lake Ontario with a decent wind I wanted to get the sails up as quickly as possible. This never works well with us. My impatience of doing everything quickly (and usually wrong) vs Lori’s slower methodical process collided. We swore at each other, threatened to split the boat up, cursed and stormed while we fumbled with the sails. During our tantrums, the boat from Cobourg had unfurled both their main and genoa and were about to sail past us (OK, second thing to admit,I’m also a bit jealous of boats with furling mains). By this time, we calmed down and apologized to each other. Note: Since then, we’ve come to the agreement that we will always curse at each other while getting the sails ready but will always forgive each other once we are under sail. This has been working well for us. As we looked behind us, there was a second sailboat motor sailing and catching up to us, up ahead we see a third boat going the same direction as us with both sails up. Lori’s demeanor changed again, and the competitive bug must have bit her because the race was on! 

It was a slow race, but we had lots of time. We did well, with 17 knot winds we were doing a consistent 7 knots. Eventually we passed the boat that was in front of us and slowly pulled away from the other two boats behind us. Lori was happy.

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Wind speeds started to pick up and we decided to try furling the genoa to reduce our heel. Lori attached the the furling line to the winch and we headed into wind but the genoa sheets got tangled up and we ended up drifting to a stop. We headed off wind, picked up some speed and tried a second time, unsuccessfully. Third attempt, we made sure all of the lines were clear and ready to be pulled in and we were finally successful. The boats we passed earlier had gained some considerable distance on us, but we were still ahead. 

The next couple of hours were uneventful, other than Lori’s sailing personality came out again. She started coming up with new exercises that can be done on the boat while heeled over. 

Around noon, the wind died down suddenly from 20 knots to 8 knots and shifts direction slightly, we unroll the Genoa and realize that our “reef” was only six inches of sail. Looks like we need a bit more practice reefing. As things calmed down, we decided it was a good time to make lunch. 

Then the wind continued to drop, 5 knots, 3 knots… our boat speed drops to 1.3 knots and we reluctantly decide to start up the motor. Still had some distance to go, but we had a good sail up to this point. Kicked on the auto helm and lounged about for the rest of the trip to Port Whitby Marina. The kids kept themselves busy by reading and inventing new ways to get rid of the unwanted swarms of flies that found us. 

At one point, Owen was using the vacuum to suck up the dead flies and started playing with the buttons on the top. He didn’t realize that one of the buttons open up the vacuum for cleaning and he ended up with a pile of dead and some alive flies all over him. 

We arrived at Port Whitby Marina at 2:20pm. It took us almost six hours.

Entrance into the marina was a little bit confusing. It’s well marked, but there are lots of shallow spots to avoid. I was nervous we were going to touch bottom and the depth sounder kept reminding me we were close. The marina staff was great on the VHF, directing us to our slip. 

Checking in, we met another nice couple in the office and quickly discovered we knew them! Their sailboat, Pawby, is kept in Cobourg, just a few slips away from our boat! I’m still surprised how easy it is to run into friends within the boating community.

We decided to explore Port Whitby that night. It’s a bit industrial around the marina but there are lots of stores and places to check out within walking distance (20-30 mins). A quick search on Google Maps and we found Town Brewery was walking distance away so we had to check it out.


We discovered that there wasn’t much for food, but they had a few simple snacks that were good. They also had a good selection of board games to play. So we ordered two flights of samplers, a few snacks and played a few games before deciding to find another place for a more substantial meal. Beer was OK but everything was an unfiltered style that wasn’t our favourite.

We went for another walk and found the Royal Oak for a more substantial dinner, and maybe a few more drinks. Afterwards, we walked back to the marina and enjoyed a beautiful sunset with the other boats. 

Lessons Learned

  1. We are still learning how to quickly hoist the sails. And we will have different opinions and different ways we want to do it. During this time of frustration we found it better to just let it all out but the agreement is that once the sails are set all is forgiven. 
  2. Similar to the first lesson, my rush to do things quickly doesn’t always mean it’s faster. When we tried to furl the genoa we would have been better to spend a few extra moments to better prepare everything before attempting to pull in the genoa.