St. Michaels Sailing Charters

Boating, Fishing & Historic CruisesSt. Michaels Boating, Fishing & Historic Cruises

Hours:

April thru November, 9am thru 9pm, Monday thru Friday.

Driving Directions:

Located at the Harbour Inn, Marina and Spa

About Us

Looking for a relaxing boat tour in Saint Michaels on the Chesapeake Bay? Hoping to get out on the water, unwind, and spend some time in nature? If you’re searching for things to do in St. Michaels, MD or exploring the top local attractions, our luxury sailing yachts—Lady Patty and Epiphany—are the perfect choice. From historic charm to modern comfort, St. Michaels Sailing Charters will take you out for a memorable and peaceful day under sail.

Choose between our two stunning sailing yachts: the historic Lady Patty, a 1935 Maryland-built ketch, or Epiphany, a spacious and modern 44-foot Leopard catamaran. Each sail includes a two-hour (or longer) cruise with knowledgeable, first-class captains and a friendly crew dedicated to creating an unforgettable experience. Enjoy our popular day sails or opt for specialty outings like sailing lessons, wine and beer tasting cruises, and more.

Our sailing yachts are docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland—a charming Eastern Shore town known for its incredible seafood and inviting small-town atmosphere. Whether you’re planning a day trip to St. Michaels or seeking a sailing charter on the Eastern Shore of the Chesapeake Bay, our relaxing sailboat excursions are conveniently located just 90 minutes from Philadelphia, Baltimore, and Washington, D.C., and only an hour from Annapolis.

Out on the open water, our sailboats offer your choice of a public or private cruise in one of the most beautiful places to sail. Chesapeake Bay sailing is renowned for its stunning scenery and unforgettable sunsets.

Highlights

Images

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Events

Two Hour Chesapeake Day Sail on Lady Patty

Two-hour public or private sailing cruise aboard the historic 1935 ketch Lady Patty on the Chesapeake Bay.
Friday Apr 17, 2026

Two Hour Relaxing Chesapeake Day Sail on Epiphany

Two-hour public or private sail aboard a 44-foot Leopard catamaran on the Chesapeake Bay with experienced captains and crew.
Friday Apr 17, 2026

Wine Tasting Cruise

Sip, savor, and sail! Experience a unique blend of wine tasting and scenic sailing with St. Michaels Sailing Charters.
Friday Apr 17, 2026

Beer Tasting Cruise

Sip, savor, and sail! Experience a unique blend of craft beer tasting and scenic sailing with St. Michaels Sailing Charters.
Friday Apr 17, 2026

Half-Day Private Sails

Cruise through historic St. Michaels Harbor, then sail up the scenic Miles River on this unforgettable half-day adventure.
Friday Apr 17, 2026

Full-Day Private Sail

Enjoy a full 7 hour day of sailing in the beautiful waters of the Miles River on Chesapeake Bay.
Friday Apr 17, 2026

Bachelorette/Bachelor Party Cruise

Celebrate your bachelorette or bachelor party in unforgettable style aboard our historic 1935 ketch Lady Patty or modern 44-foot catamaran.
Friday Apr 17, 2026

Marriage Proposal Engagement Cruise

Engagement romantics pick St. Michaels Sailing Charters for a totally unforgettable nautical wedding proposal on a private sailing yacht.
Friday Apr 17, 2026

Chesapeake Bay Sunset Champagne Cruise on Lady Patty

Relax as you sail into golden hour on the Chesapeake Bay, sipping champagne while the sun sets aboard Lady Patty.
Friday Apr 17, 2026

Chesapeake Bay Sunset Champagne Cruise on Epiphany

Relax as you sail into golden hour on the Chesapeake Bay, sipping champagne while the sun sets aboard Epiphany.
Friday Apr 17, 2026

Two Hour Chesapeake Day Sail on Lady Patty

Two-hour public or private sailing cruise aboard the historic 1935 ketch Lady Patty on the Chesapeake Bay.
Saturday Apr 18, 2026

Full-Day Private Sail

Enjoy a full 7 hour day of sailing in the beautiful waters of the Miles River on Chesapeake Bay.
Saturday Apr 18, 2026

Half-Day Private Sails

Cruise through historic St. Michaels Harbor, then sail up the scenic Miles River on this unforgettable half-day adventure.
Saturday Apr 18, 2026

Beer Tasting Cruise

Sip, savor, and sail! Experience a unique blend of craft beer tasting and scenic sailing with St. Michaels Sailing Charters.
Saturday Apr 18, 2026