Labor Day 2025: Gibson’s Island and Chester River

Our standard Labor Day sailing trip involving the Chester River brought needed relaxation.

We have developed some routines in our Summer anchorage plan now that we’ve been in Maryland for a few years. Labor Day seems to involve the Chester River, and with Skyward based on the Patapsco, the trip was shorter than last year. This trip included 3 relatively well-known overnight stops: Gibson Island (Horse Farm/Eagle Cove), Corsica River, and Cacaway Island. This blog post is more of a picture book than a story – less words, more pictures.

Gibson Island, Corsica River and Cacaway Island

We motor-sailed down to Gibson Island on Friday. We dropped the anchor just as the sun went down. We had the perfect Westerly view because we anchored closer to the Horse Farm.

Gibson Island near the horse farm looking due West

We didn’t know our friends were there, because we arrived so late and we were paying more attention to getting food made and watching the sunset. It was serene and peaceful watching the horses and activity at the horse farm. I especially liked seeing the horse farm majestically lit up at night.

The next morning we raised the anchor and headed towards Corsica River up the Chester. Along the way, we received a text from our friends that said something like “we are coming for you”. I looked back and saw them creeping up to us. So we jumped into race mode. This picture shown below is before “race mode” began…I don’t want to give away any of our secrets during the race. There is a debate about who one the race. I’ll be happy with just saying we held our own.

Rachel mastered the helm, and I expertly trimmed the sails for the race

We finally hoisted the asymmetrical spinnaker on Skyward just after we entered the Chester River. The wind dropped down in the 5-7 knot range, so it was perfect conditions for our first try. I think we did pretty good. Dousing it was very simple with the mainsail shadowing it.

Zaoli Asymmetrical Spinnaker lauched double-handed

We got to Corsica and put our feet up. The anchorage was just on the North side of the river after entering. It was well-protected from Northerlies and therefore, calm. There were some party boats at the sandy beach, but there were not too roudy. Every now and then a power boater would traverse the Corsica River and throw a wake, but most of the time it was peaceful.

We picked up the anchor the next morning and motor-sailed out of the Corsica River, across the Chester River and up Langford Creek. Along the way, we ended up having some miscommunications and that resulted in a torn leech of the genoa. I laugh now, but it wasn’t humorous when it happened. I was trying to prevent it from happening, but I froze up and didn’t act fast enough. As a sailor, I need to work on annunciating and then taking control when my instructions do not result in the proper actions. I kept repeating words, but they ended up being the wrong words, which made the whole situation frustrating.

Torn leech on the North Sails Genoa

The leech has already been repaired by the Quantum loft in Annapolis. Nonetheless, we got to the anchorage we like near Cacaway Island, and we set the anchor. Time to relax.

And then it happened…the heavens did not disappoint. I couldn’t wait to drink a cold beverage after that lousy sail. These pictures have no filters or AI applied.

A nice cold soda went well with the awe inspiring sunset that we were about to experience

We paddled over to Cacaway Island and just stood there mesmerized over this sunset and the clouds. It seemed that the sunset took an hour even though it was over and done in just minutes. I first grabbed a panoramic shot before the sunset became “the sunset”:

Then as the sun kissed the tops of the trees, I stepped back on the island and caught this fallen tree laying in the water on the beach:

That’s when it got interesting and all of the whispy clouds started getting lit up:

Here is just before the sun ducked below the treeline:

Looking back at our floating home, all we saw was pink:

After dinner on Skyward, we paddle boarded over to our friends boats where we enjoyed their company and watching the last of the sunlight disappear. As it got late, we decided to paddle back to Skyward several boat lengths away. Scary not scary.

And that was about it. The next morning we had the perfect sailing conditions leaving the Chester River with about 10-12 knots on close reach all the way up to the Patapsco River. As always, we had a lot of time to think and ponder. The way back home gave us a break from having the constantly tack and change course. Thank heavens!

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Author: Jeff Lukowski

Based out of Annapolis

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