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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.
Beer Tasting Cruise
Sip, savor, and sail! Experience a unique blend of craft beer tasting and scenic sailing with St. Michaels Sailing Charters.
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.
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.
Full-Day Private Sail
Enjoy a full 7 hour day of sailing in the beautiful waters of the Miles River on Chesapeake Bay.
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Half-Day Private Sails
Cruise through historic St. Michaels Harbor, then sail up the scenic Miles River on this unforgettable half-day adventure.
MARGARITA MONDAYS at San Miguels
Kick off your week at San Miguels with Margarita Monday! Enjoy BOGO on Specialty Margaritas and pair them with our delicious house-made empanadas.
Marriage Proposal Engagement Cruise
Engagement romantics pick St. Michaels Sailing Charters for a totally unforgettable nautical wedding proposal on a private sailing yacht.
Monday Night Trivia with DJ Chuckie
Weekly Monday Trivia Night at Corah’s Corner in St. Michaels, MD. Trivia from 6–8 PM, prizes, food & drink specials, plus karaoke after. A fun night out.