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Lady Patty Sail Charters

Office - 21426 Wharf Rd, Boat - 6176 Tilghman Island Rd, Tilghman, MD 21671
+1 410-886-1127
Review Highlights
Fabulous Sunset Sail

The crew is great! Emma and Joe took care of everyone very well. We got to sit back and enjoy the... read more

Reviewed 2 days ago
Ellicott City, Maryland
Great Experience

We opted for the Sunset Champagne Cruise. It was a perfect evening.More than enough wind to be able... read more

Reviewed 26 September 2016
Charles L
Read all 87 reviews
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The classic yacht Lady Patty departs three times daily for the beautiful Chesapeake Bay from Tilghman Island, MD, just twelve scenic miles past St Michaels, MD from April 1 through October 31. Lady Patty is a 45' sailing yacht built in 1935 for offshore racing. She carries over 1000 square feet of sail and is USCG inspected for 16 passengers. During charters beer, wine and drink service is offered. We specialize in Champagne Sunset Sails. Don't settle for sailing in the rivers and harbors. Join us aboard the only sailing vessel in the area that sails on the open Chesapeake Bay. Come sail away aboard the classic yacht Lady Patty.
  • Excellent98%
  • Very good2%
  • Average0%
  • Poor0%
  • Terrible0%
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Hours Today: 10:00 - 12:00
Office - 21426 Wharf Rd, Boat - 6176 Tilghman Island Rd, Tilghman, MD 21671
+1 410-886-1127
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Reviews (87)
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1 - 10 of 87 reviews

Reviewed 2 days ago

The crew is great! Emma and Joe took care of everyone very well. We got to sit back and enjoy the sights and glide along the water. Even though the evening was cloudy, we were able to see about 50 dolphins frolicking in the water...More

Thank Nurps
Reviewed 26 September 2016

We opted for the Sunset Champagne Cruise. It was a perfect evening.More than enough wind to be able to sail. Captain Jeff and the first mate(his young son) were very knowledgeable and hospitable. Margaritas and champagne made the evening that much more relaxing! The sunset...More

1  Thank Charles L
Reviewed 15 September 2016 via mobile

Had a beautiful sail boat trip to watch the sunset. Throughly enjoyed visiting with the captain and Sarah did a great job taking care of the passengers. Throughly enjoyed and would highly recommend sailing with this crew! Thank you for a great evening!!

1  Thank Deanna B
Reviewed 7 September 2016

We took the "Sunset Champagne Cruise" provided by Captain Jeff and his crew aboard the Lady Patty during our visit from Seattle. To say it was romantic was an understatement! Jeff and Sara, his first mate could not have been more accommodating. Serving up drinks...More

1  Thank Carl H
Reviewed 22 August 2016

We went on a beautiful sunset sail and had a realy nice sailing experience. The boat is beautiful and the captain very hospitable. And the sunset was outstanding

1  Thank F6980BTpaul
Reviewed 6 August 2016

What an amazing way to experience the countless colors of the sunset over the Chesapeake Bay- on a historic sailboat with good friends, delicious drinks and a friendly captain and crew. Can't wait to return to the Lady Patty for another perfect sail!

1  Thank marymac1969
Reviewed 26 July 2016

Captain Jeff and his first mate Emma were so accomplished and at ease with the sailboat that I felt as if I were floating on a cloud at times. Prone to seasickness, I always approach any smaller sized boat with a bit of trepidation-- so...More

Thank M H
Reviewed 14 July 2016 via mobile

I scheduled a Saturday evening sunset cruise. I messed up the time and missed our sail. Capt Jeff fit us in Sunday morning for an amazing sail around the entire island. Super nice people. You can't go wrong with the beautiful Lady Patty.

Thank Keith W
Reviewed 3 July 2016

There were ten of us and we had the boat to ourselves. The ride was beautiful. The captain Jeff and his first mate Emma could not have been more pleasant. Very congenial and knowledgable . It was a wonderful smooth sail.

Thank Shel3736
Reviewed 28 June 2016

We were on Tilghman Island for an anniversary trip and wanted to do something "nautical" so after reading the reviews and getting a recommendation from a local innkeeper we choose to book with the Lady Patty. We went out for a two hour morning sail....More

Thank esl1860
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded 29 June 2016

Thanks for the kind words! I appreciate your business and you taking the time to give us a review! I hope to see you again on your next visit to Tilghman Island. Cheers! Jeff

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Questions & AnswersAsk a question
pat m
Hi, if you sail out of St. Michaels then you provided us with a the sail boat ride that made me fall in love with sailing!!! Now we are looking to sail out of Baltimore or Annapolis (I think you mentioned to us that you sail out of there as well.) I was wondering if you have a sail boat tour that included any lighthouses. Also,do you sail during the week or just weekends? When does your season begin? Thanks so much!! Pattir
18 April 2015|
Response from duskyjeff | Property representative |
Hello Pattir, Thanks for your inquiry about the Lady Patty! I'm glad you enjoyed sailing with us, We do sail in Annapolis on occasion but normally as a Private Charter. In the event of being there already we will offer... More