2-Hour Relaxing Chesapeake Day Sail on Lady Patty

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2-Hour Relaxing Chesapeake Day Sail on Lady Patty

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 US$169.89  per guest
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Adult x1
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Select a Date
Check Availability
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Instant Confirmation
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Available Today
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
2 hours
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Number of Guests
1 - 13 guests
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Language
English
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Other
Private Experience
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Digital Ticket
Mobile or paper ticket accepted
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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding through the harbor and possibly spotting wildlife like osprey and dolphins. Enjoy a friendly crew that shares captivating stories about the area and sailing. Whether you’re looking for a fun family outing or a peaceful escape, this sailing experience is perfect for all ages.


- Duration: 2 hours, with daily availability

- Max capacity of 13 guests, ensuring a personalized experience

- Beer and wine tasting available for adults, with complimentary water

- Departing from Harbour Inn, 101 N Harbor Road, St. Michaels, MD

What You Get

Life jackets
Bottled water
Rain jackets
Swag items available for sale
Alcoholic beverages
Beer and wine are available for sale
Carbonated beverages
Soda available for sale

Good To Know

  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Service animals allowed

What You’ll Experience

1879 Hooper Strait Lighthouse (Pass By)

The Hooper Strait Lighthouse is one of only four remaining Chesapeake Bay screw-pile lighthouses in Maryland. At the start and close of your charter, Lady Patty glides past, offering a beautiful, up-close view of this historic beacon.

Meeting & Pickup

Meeting Point

St. Michaels Sailing Charters, North Harbor Road, Talbot County Maryland, United States, US, 21663

Open in Google Maps
From Easton, take Route 33 (St. Michaels Rd) into St. Michaels. Go through town past the blinking light at the firehouse. Turn right on Chew Ave, then left onto N Harbor Rd. Follow it to 101 N Harbor Road at St. Michaels Harbour Inn, Marina & Spa.
End Point

This experience ends at the meeting point.

Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund.

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Reviews
4.9
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based on 21 reviews
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(TripAdvisor)
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Sailing at its finest!
September 01, 2026

A relaxing time with Captain Rob and his mate Steph. A great experience while in St. Michaels.

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(TripAdvisor)
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When a Captain makes time stand still.
August 26, 2026

Pleasant afternoon on the water with sails up and boat flowing through as only Lady Patty can do! Can’t wait to go again soon. Sue H.

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Very nice boat, no wind, just went out aways into the Bay
August 25, 2026

The boat was in very nice shape, well taken care of. The crew members were very nice. The food we ordered from a local place was delicious and had just been delivered as we walked up. My only thing...read more

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(TripAdvisor)
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Wonderful experience on the water
August 17, 2026

Wonderful experience. Highly recommend if you wish to have a “on water” perspective of Chesapeake bay.

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Wonderful sunset cruise
August 15, 2026

Wonderful sunset cruise; beautiful boat- very relaxing and worth the money paid.

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