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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.
All Day Happy Hour, Sundays at The Fool's Lantern
Join us every Sunday for an all-day happy hour with amazing drink specials! Enjoy $8 crushes, $7 mimosas, and $6 select draft beers all day long!
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.