St. Michaels Sailing Charters

09/04/2026

What’s better than a girls’ day? A girls’ day on the water, of course! ⛵🥂

There’s nothing like sunshine, good company, and a breeze off the Bay! Grab your favorite girls and let us handle the rest. Private group sails are the perfect way to celebrate a birthday, bachelorette, or just because!

Ready to set sail with your crew? Link in bio to book your own girls’ day cruise. 🌊✨

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Keywords// Girls trip, group sail, sailing charter, St. Michaels MD, Eastern Shore, Chesapeake Bay, bachelorette cruise, private boat charter, ladies day, on the water

09/03/2026

Ready to elevate your sailing skills? ⛵
Learn to confidently handle and charter a cruising catamaran aboard Epiphany, our Leopard 44!

📅 September 28-29: 1 spot left
📅 October 5-6: 2 spots left

Prerequisite: ASA 104 Bareboat Cruising

Book online at: stmichaelssailingcharters.com or email us at: [email protected]
[link in bio]

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keywords// ASA 114, Cruising Catamaran Certification, Catamaran Sailing Course, St. Michaels Sailing Charters, Sailing Lessons Maryland, Chesapeake Bay Sailing, Learn to Sail, Multihull Sailing, ASA Certification, Bareboat Charter Training

09/02/2026

Say hello to “The Chesapeake Elevated” ⚓️

Our partnership with Hambleton House Events and Catering bringing Jumbo lump crab parfaits, chilled Old Bay shrimp skewers, classic deviled eggs, and house-baked cookies, all served up underway. This is coastal entertaining, elevated. 🦀🍤

Book your charter and taste the Bay the way it’s meant to be enjoyed.

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keywords// Chesapeake Bay catering, St. Michaels sailing charter, private boat charter catering, crab parfait, Old Bay shrimp skewers, coastal event catering, Hambleton House Events and Catering, waterfront charter dining, Maryland Eastern Shore events, private sail charter

08/28/2026

Lucky for you, we offer them every day of the week! ⛵️

Book your spot aboard Lady Patty or Epiphany and watch the Chesapeake light up in the most magical way!
[link in bio]

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keywords// Sunset sail, St. Michaels sailing charters, Chesapeake Bay, Lady Patty, Epiphany, sailing cruise, Eastern Shore, golden hour, wooden ketch, catamaran

08/27/2026

Proposals aboard Lady Patty just might be our favorite… I mean, can you blame us? 😍⛵️

Congratulations to the newly engaged couple, Justin & Abby! From all of us at St. Michaels Sailing Charters, we wish you a lifetime of the sweetest memories, adventures, and smooth sailing ahead.

P.S. First Mate John pulled double duty as crew and impromptu lighting assistant… what can’t he do?

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keywords// St Michaels Sailing Charters, Lady Patty, sailboat proposal, she said yes, engagement, St Michaels MD, Eastern Shore MD, Chesapeake Bay, sunset proposal, wooden sailboat, tall ship, sailing life, just engaged, proposal ideas, romantic sailing

08/24/2026

When life gives you a little extra time… spend it on the water. Where the views are better and the pace is slower. That’s the St Michaels way. ⛵

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keywords// sailing charter, St. Michaels MD, Eastern Shore sailing, sunset sail, Chesapeake Bay, private charter, boat tour, waterfront experience

08/20/2026

Some reviews just capture it perfectly and this one was too good not to share! 🌅⛵

Thank you, Kathy, for sharing your evening aboard the Lady Patty with us, twice now! There’s nothing quite like golden hour on the Miles River!

Ready for your own escape into serenity? Book your sunset sail with us. Link in bio.

⭐⭐⭐⭐⭐

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keywords// Sunset sail, Miles River, St. Michaels harbor, Lady Patty, 1935 wooden ketch, restored schooner, Eastern Shore sailing, Chesapeake Bay cruise, sailing charter, five-star review, local guide, golden hour, harbor views, relaxation on the water, repeat guests, book your sunset cruise

08/15/2026