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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.
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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.
Wine Tasting Cruise
Sip, savor, and sail! Experience a unique blend of wine tasting and scenic sailing with St. Michaels Sailing Charters.
Beer Tasting Cruise
Sip, savor, and sail! Experience a unique blend of craft beer tasting and scenic sailing with St. Michaels Sailing Charters.
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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.
Full-Day Private Sail
Enjoy a full 7 hour day of sailing in the beautiful waters of the Miles River on Chesapeake Bay.
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.
Marriage Proposal Engagement Cruise
Engagement romantics pick St. Michaels Sailing Charters for a totally unforgettable nautical wedding proposal on a private sailing yacht.
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.