I have a pretty close relationship with my younger sister, a closer relationship the most older brothers and younger sisters, but that relationship does have its boundaries. For example, I did not attend the mentally scarring event also known as her bachelorette party. Instead of being present for that highly awkward situation, her finance Matt and I decided to go for a overnight sail on the Chesapeake Bay.

I will admit to being a bit nervous about this adventure, and not because of a fear of being lost at sea. I have known Matt for nearly a decade and this would be the longest time we’ve ever spent one-on-one together. 

I arrived at Sandy Point State Park at the foot of the Bay Bridge a bit later than planned but still was able to beat the boat, which Matt was bringing down from their house in West Virginia more than 70 miles away. If you’re not from Maryland you may not realize Bay Bridge traffic tends to back up a lot on Fridays in the summer. You only have one place in Maryland to cross the bay, and that’s the bridge near Annapolis. The incredibly high bridge is tall enough to let cruise ships and freighters easily pass underneath. The height is so intimidating to some drivers

a service used to be offered in which a pilot car would lead you over the bridge.

When Matt arrived it didn’t take long to raise the mast and rigging (stowed for transport) of the 22-foot Catalina. We eased her (since all boats are girls) into the water, then picked up and filled out our yellow tags which we tied to our antenna to let the park service know where we were heading and that we planned to be out over night.

We pushed off and headed out under our the power of the small electric motor, which made it easier to navigate the narrow channel from the harbor. We ran up the rigging and the sails and caught a gust of wind and were off at a good clip. But that didn’t last long.

The bay is notorious for its wind dying out around 3 p.m. When you’re on a sailboat that becomes a problem. We slowly limped along at about one knot (just under a mile an hour) for the next four hours. We had some fits and spurts of conversation and that was fine. I’ve never known him to be to chatty and the simple peace and calm of the water and gentle breeze was good enough for me.

It was around 7 p.m. when the wind picked back up, just in time to set us on course for the cove on the far side of Sandy Point where we would anchor for the night. The far shore was dotted with homes and summer homes of some of the Annapolis elite, each with its own dock and a boat bobbing in the water.

With our anchor dropped, our small Catalina became a transformer. The roof for the cabin extended up and the sun shade the over the cockpit doubled the live-aboard space. I wisely remembered to bring a large mosquito net, a lesson learned in Virgin Gorda, which we draped over the sunshade freeing us from the threat of horseflies and other biting bugs. We listened to music and had a little to eat as the sun began to set. I even made time to FaceTime Amanda. A sunset over the water is a beautiful thing and even more amazing as it set in the west the full moon began to rise in the east moments later.

It was a long day. As usual, I had gotten up at 1:30 in the morning and all the activity had me pretty tuckered out. The gentle rolling of the boat on the water rocked me into a sound sleep. I’m good at sleeping in the sunlight, which is good since I was sleeping out in the open on the deck, and wasn’t ready to get up with the sunrise. We pulled in the netting and scarfed down the last of the donuts Andrea had sent along for us before setting sail for our return leg.

Our return trip featured one thing we didn’t have the day before: wind. A stiff breeze carried us to the breakneck speed of 6 miles per hour. It wasn’t long until the bay was filled with sails catching the precious wind on a hot summer day. I took the helm as we made a bee-line for the bridge. We’d charge into the wind the tack over at the middle of the span and let the southerly wind carry us to the channel. We worked great together tacking back and forth getting the most out of our head wind.

The teamwork truly became important in an instant as a gust came up, pushing the boat onto its side. I dove down with the tiller and turned her dead into the wind causing the jib to flap as Matt jumped over me to release the boom and spill all the air from our sails and right the boat. The excitement only lasted a moment, but it was enough for us both. We were close to the channel so decided to go ahead and lower the sales and power up the electric motor for the final quarter mile.

We pulled her out of the water and packed up the sails and mast, relaxed and recharged for the rest of the week. I have to admit there was nothing to be nervous about. We didn’t talk much, but the simple act of sailing together was a bonding experience and a good one for future brothers-in-law.