Sailing Winds' Pleasure

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Sailing Winds' Pleasure A couple of wannabe pirates sailing wherever the wind takes them.

Sporty sideways sailing to Solomons today. Small craft advisory? Hold my root beer. 🌬️ ⛵
31/10/2025

Sporty sideways sailing to Solomons today. Small craft advisory? Hold my root beer. 🌬️ ⛵

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We didn't intend to be here for the Sailboat Show, but still waiting on parts to be delivered. So, who's in town? Let's ...
08/10/2025

We didn't intend to be here for the Sailboat Show, but still waiting on parts to be delivered. So, who's in town? Let's hang out! 😍

04/10/2025

Poor robot.

On our way up to Georgetown, our 40 year old headsail trim track decided enough was enough and broke in two. Caught it b...
20/09/2025

On our way up to Georgetown, our 40 year old headsail trim track decided enough was enough and broke in two. Caught it before anything went bad, so back in Annapolis to source a new one for both sides - cause surely the other side is just as bad off.

Hoping for an easy find and project (HA!) so we can start meandering south. We'll probably be here for a week or two, so let us know if you're in the area so we can visit!

On our way up to Georgetown, our 40 year old headsail trim track decided enough was enough and broke in two. Caught it before anything went bad, so back in Annapolis to source a new one for both sides - cause surely the other side is just as bad off. Hoping for an easy find and project (HA!) so we c...

14/09/2025

Went for a light wind, drift sail with a friend yesterday. Vin and Tobey checked in on each other from across the water 😂

Hanging out on the Sassafras River for a bit. I'm behind on posting, so will catch up soon. 💜 ⛵️
10/09/2025

Hanging out on the Sassafras River for a bit. I'm behind on posting, so will catch up soon. 💜 ⛵️

Heading to Baltimore! Drop suggestions on what to see or where to eat in the comments! Close to inner harbor and dive ba...
25/08/2025

Heading to Baltimore! Drop suggestions on what to see or where to eat in the comments!

Close to inner harbor and dive bars/local spots preferred 👍

If you haven't visited the Maryland Renaissance Festival, you absolutely should! It truly felt like we were transported ...
24/08/2025

If you haven't visited the Maryland Renaissance Festival, you absolutely should! It truly felt like we were transported back in time!

I was pretty excited to see Jacques ze Whipper and Paolo Garbanzo and they didn't disappoint. Fantastic day off the boat 😍

Tomorrow we head to Baltimore 👍

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