Check the schedule and buy your tickets here!


Welcome to!

Lady Patty Classic Yacht Charters offers two-hour public Chesapeake Bay sailing trips for up to 13 passengers daily from Wednesday through Saturday with a limited schedule on Sunday and Monday. We are closed for public sailing on Tuesdays.

Morning Sail 10:00AM – 12:00PM-$45 per Adult $25 Kids 12 or younger

Afternoon Sail 1:00PM – 3:00PM-$45 per Adult $25 Kids 12 or younger

Champagne Sunset Sail  (times vary) – $50 Per Person, includes complimentary champagne

*It is tradition on the Chesapeake Bay that 1st Mates work for tips. 15-20% of the total cost is customary if they take excellent care of you. 


You can check the schedule and buy your tickets here. 

*Please save a tree and refrain from printing your online tickets. If you purchased tickets by phone or online both you and I will receive an email confirmation. Your name will be on the list. Cheers!

We are open for business from May through the end of October.

Almost all of our regular trips depart from Knapps Narrows Marina just before the drawbridge to Tilghman Island. The exception to that is our Friday Night Sunset Sails which depart from the beautiful Wylder Hotel on the Island.

Soft drink, beer, wine and cocktail service is available on all charters. Catered food is also available from local restaurants by special arrangement.

While underway on the Chesapeake Bay you will be treated to a true sailing experience by a seasoned professional crew who knows the Tilghman Island area well. Once underway from the dock we will motor for five minutes then hoist over 1100 square feet of sail and go. We can often reach the main shipping channel or half-way point across the Bay during our two-hour excursions.

You can enjoy a cold craft beer or Sunset Gold Margarita served to you on deck while under sail during your trip.

The Captain and the First Mate will gladly answer any questions that you might have. We love sharing bits of the long and illustrious story of our Lady of the Bay including tales of offshore racing, ocean voyages and foreign ports during the golden age of yachting.

Check the schedule and buy your tickets here!