I’ve been wanting to get to St. Michaels since before we moved to Maryland. There are many YouTube channels and blogs that talk this place up. Since May, either the weather hasn’t cooperated or we have had too many things going on. Moving from one state to another can really suck the life out of a plan to sail the Chesapeake Bay all Summer.

We left Chesapeake Harbour Marina shortly after 9am at high tide. The previous weekend, we came into the marina at low tide and we got stuck coming in. We drifted off the channel maybe 10 feet. I used the throttle like the handle of a golf club; to get the job done. I found that putting the boat into reverse didn’t do much. It wasn’t under I pointed the bow directly back into the channel with the bow thruster that we could inch our way off the unseen shoaling. Something about being a couple hundred yards from your marina and getting stuck that makes you want to hurry up and get unstuck and act like nothing happened.

Leaving the marina on a broad reach, we decided to pull out the genoa. I saw ‘pull out’, because our furling/unfurling our headsails on Skyward is 100% manual. After we did this, we thought…’wouldn’t it be nice to also have the mainsail up to give more sail area?’. I should’ve thought that idea through a little sooner. After watching the wind and looking for stability, we decided to raise the main while maintaining this tack; wind between 120-150 degrees. I loosened the mainsheet, and then went up to the mast and pulled back the lazy jacks on the leeward side. I was able to pull up the main in a controlled manner at the mast by wrapping the halyard around one of the 5 winches we have there. This process worked, however, I could not prevent the main from rubbing along the spreaders. Next time, we will raise the main first!
In under two hours, we rounded Bloody Pt and started what would become several short tacks. Across and then back down in the Eastern Bay until we got to Wades Pt then we got a fresh 15-20 knot breeze on our port side unexpectedly. Skyward just heeled over gently and picked up 2 knots of speed. We rounded Rich Neck and our sailing turned to motoring.

The wind died down quickly we as turned South towards Hambleton Pt. We made it to St. Michaels in 5 hours and dropped the hook in a very calm anchorage. Although, we were in shock about how many jellyfish we saw in the water – gave us the heebie jeebies


We dinghied around the harbor checking out all of the nooks and crannies before we stopped at the dinghy dock. It was great to stretch our legs, stroll the town streets, and walk down to Awful Aurthur’s for crab cakes.


There were so many things to see in this town,”; needless to say, it lived up to the hype. We followed that with some ice cream and then back to the boat for a quiet evening watching the sunset and moon rise. Both events were absolutely spectacular.
The next morning we pulled up anchor and headed back home for another busy work week ahead. I left this place fulfilled and glad we took the time to check it out. We will definitely be back in 2023. But I can’t end this post without showing some amazing footage of Skyward in the anchorage.








