Tours/Maryland/2-Hour Relaxing Chesapeake Day Sail on Lady Patty
Viator · Private tour

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

5.0(12)Maryland1 hour
TRIPADVISOR5.0(12)

Description

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

Tour Options

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Itinerary

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.

Highlights

Life jackets
Bottled water
Rain jackets
20% Gratuity for Captain & Crew
Free parking
Binoculars
Government Fees

What's included

Included
Life jackets
Bottled water
Rain jackets
20% Gratuity for Captain & Crew
Free parking
Binoculars
Government Fees
Not included
Swag items available for sale
Beer and wine are available for sale
Soda available for sale

Traveller Ratings

5.0
12 reviews
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12
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Important Information

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

Reviews(12)

M
mfhebert1966
August 16, 2026
Wonderful experience on the water

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

M
MichaelE598
August 14, 2026
Wonderful sunset cruise

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

V
V5169ZAkathym
August 13, 2026
Sailing to serenity

As we gliding over the smooth waters of the Miles River our sunset cruise aboard the Lady Patty, a stunningly restored 1935 wooden ketch, was not just a journey but a delightful escape into serenity. With the sun casting golden hues across the horizon, the friendly and knowledgeable crew guided us through the breathtaking scenery of St. Michael's harbor, were we treated to a feast for the senses. This experience was a perfect blend of relaxation and exploration, reminding us that sometimes, the best therapy is found on the water. This being our second cruise, we look forward to set sail again and catch the winds of adventure; after all, life is better when you’re cruising through it!

D
Discover19431217044
August 13, 2026
Lady Patty , a sailor's dream

An amazing sail on an amazing boat. We are experienced sailors and the boat performed beautifully. The crew was very knowledgeable and personable. Our crab cakes and wine added to the fun. We can't wait to sail on her again.

C
Curiosity730049
August 8, 2026
An absolute must-do if you are anywhere near St. Michaels MD

The captain, GM, and mate, Brian, were the best! They made the trip interesting, fun, and so fulfilling. The sunset cruise was perfect -- perfect enough that the captain was himself taking pictures and sending them to his wife. How sweet is that? The Lady Patty was recently completely renovated by GM and his team; it felt like we were sailing on a brand new boat, not a 91 year old. This was the highlight of our stay in lovely St. Michaels. When GM turned off the engine and we were just powered by the wind, we felt a peace and calm that is often missing in our lives. Thank you GM and Brian!

A
Ambassador823756
July 26, 2026
Sailing and beer tasting

My partner and I sailed the Lady Patty with the beer tasting option. It was very relaxing on the bay, just a chill ride with the breeze. We got to help out a little with raising the sails, but otherwise just enjoying hanging out and drinking beer! Brian and Yvonne were our captain and mate, and they were enjoyable to talk with. We booked the day of the sail, and it was a really fun two hours on the Bay.

R
rob b
July 14, 2026
Great day

We took a very relaxing 2 hour tour of the Chesapeake. Captain Rob and Brian were great. Added bonus, since we booked a trip early in the week, we were the only ones on the boat. Would do again

B
B5221VSrichardf
July 4, 2026
A true sail!

Had a beautiful sail on the river leading into the Chesapeake. The wind was sufficient so we were actually able to turn off the engine and truly sail…. Thanks

C
Camper573585
July 2, 2026
Perfect

My husband and I had an amazing sail. The captain and mate were very knowledgeable and nice. It was a perfect day. Thank you.

I
InfoSeekers
May 25, 2026
Fantastic experience provided by wonderful crew!

Thoroughly enjoyed the 5/1/26 first sunset sail on the Lady Patty, and had been looking forward to it since the 9/2/25 last sunset sail on Selina II! Wonderful people -- Captain GM, Laura Bell and the entire crew provided a truly memorable experience and we're looking forward to soon returning for an encore. Last-minute clouds muted the sunset, but we returned to harbor/marina by the light of a beautiful full moon. Can't visit St. Michaels without such sailing!

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