St. Michaels Sailing Charters

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St. Michaels Sailing Charters Best Historic Sailing Yacht Tours and Luxury Catamaran Sailing Experiences on the Chesapeake Bay!

Home is where the anchor drops. ⚓🌅

10/22/2026

Home is where the anchor drops. ⚓🌅


We welcomed the sweetest family aboard Lady Patty, and our hearts are still full 🧡💍⛵️
Congratulations to Blair & Vic on ...
10/21/2026

We welcomed the sweetest family aboard Lady Patty, and our hearts are still full 🧡💍⛵️

Congratulations to Blair & Vic on their intimate elopement on the Miles River! From the rings to the giggles to that perfect fall bouquet, this day was pure magic!

Stamped and sealed: memories from the Miles River 💌⛵
Sunsets, full sails, and slow evenings on the water. Which one belo...
10/19/2026

Stamped and sealed: memories from the Miles River 💌⛵

Sunsets, full sails, and slow evenings on the water. Which one belongs on your postcard?

Every sail tells a story. 🌅
Flags flying from the rigging. A captain with tales from the bay. Toasts on the trampoline a...
10/12/2026

Every sail tells a story. 🌅

Flags flying from the rigging. A captain with tales from the bay. Toasts on the trampoline as the sun dips behind the shoreline. Laughter at the helm.
That’s a day with St Michaels Sailing Charters.

Whether you choose our classic 1935 Lady Patty or our spacious catamaran Epiphany, we’ll handle the sailing. You just enjoy the ride!

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Annapolis, we’re headed your way!⛵ Find St. Michaels Sailing Charters at the Annapolis Sailboat Show, October 15-18. We’...
10/07/2026

Annapolis, we’re headed your way!⛵ Find St. Michaels Sailing Charters at the Annapolis Sailboat Show, October 15-18. We’ll be located in Tent D, Booth 39.

Stop by to say hi and see everything we have to offer!

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keywords// St. Michaels Sailing Charters, Annapolis Sailboat Show, City Dock Annapolis, Chesapeake Bay sailing, Maryland sailing charters, Lady Patty, Epiphany catamaran, St. Michaels MD

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101 N Harbor Road
Saint Michaels, MD
21663

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