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Lady Patty Sail Charters

100 reviews
Tilghman, MD, USA
About Lady Patty Sail Charters
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.
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Hours Today: 10:00 AM - 8:30 PM
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Reviews (100)
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All reviews captain jeff chesapeake bay worth every penny beautiful sunset beautiful trip great hosts weather was perfect surrounding area wonderful experience long time margaritas mate sail jack wind board champagne
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Reviewed 1 week ago

I confess to having sailed on The Lady Patty many times. Of course the type of sail that you will have depends a good deal on mother nature...but she is a gorgeous vessel. If you sail with Capt. Mathias you will get some great Bay...More

Date of experience: August 2019
Thank goodntention
Reviewed June 9, 2019

If one thing could make a long weekend with my family more than amazing--this was it. What a totally relaxing, exhilarating, and fun experience. We all know the Chesapeake is gorgeous, but when you're sailing on such a magnificent vessel with people who love it...More

Date of experience: June 2019
Thank runningretired2012
Reviewed May 24, 2019

Celebrated our 15 year anniversary with a sunset cruise on the Lady Patty. It was a memorable, relaxing, and wonderful experience. I highly recommend it.

Date of experience: May 2019
Thank Tamara K
Reviewed October 1, 2018 via mobile

Capatin Jeff and his First Mate Jack were great hosts while sailing on their boat the Lady Patty. They made the experience very laid back and fun. Drinks we're well prepared and attended to. The crew was able to answer any questions about the boat...More

Date of experience: September 2018
Thank georgelM1626MR
Reviewed September 8, 2018 via mobile

We’re here in a sketchy weather system with daily rain. Captain Jeff worked magic with the schedule by shifting groups all over to get our sail in today. He’s got some real pull with the weather gods! The wind - the beautiful classic 1935 wooden...More

Date of experience: September 2018
Thank Tom P
Reviewed September 4, 2018 via mobile

What a lovely time on the water. The weather was perfect and the crew was super friendly and accommodating! Well worth it!

Date of experience: August 2018
Thank Janice M
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded September 5, 2018

Thanks, Janice! I appreciate your business and the friendly words! I hope to welcome you back aboard one day in the future. Cheers!

Reviewed August 17, 2018 via mobile

We had a great time on the tour last evening. Captain Jeff and First Mate Emma were both excellent. Highly recommend this charter and their cocktails on board. Thank you both for making our 25th Anniversary such a memorable trip. The other passengers on board...More

Date of experience: August 2018
Thank Jeff H
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded August 18, 2018

Very cool! Thanks for the awesome review! I'm glad you had a good time and here's to y'all having 25 more! Maybe we'll see you on the 50th. Cheers!

Reviewed August 8, 2018 via mobile

This was my first yacht trip in a very long time. Captain Jeff and First Mate Jackson met us with warmth and friendliness that carried through the whole 2 hour tour.

Date of experience: August 2018
Thank clfromva
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded August 10, 2018

Excellent! I'm glad you enjoyed yourself. That is exactly what we endeavor to do. We appreciate the kind words and look forward to sailing with you again. Cheers! - Jeff

Reviewed June 30, 2018 via mobile

My girlfriends and I booked a sunset sailing cruise online for $50 each aboard the Lady Patty right outside the Wylder Hotel in Tilghman Island on Friday night. The cruise was worth every penny! The Captain and his mate were very informative, kind, and attentive....More

Date of experience: June 2018
Thank oibwed2011
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded July 1, 2018

Hi, Thank you for joining us Friday night and for the nice review! It was a fantastic evening and I really enjoyed your company. I hope to sail with y'all again if you ever return to Tilghman Island. Cheers! Jeff

Reviewed June 18, 2018

The captain and his crew were excellent. A really fantastic cruise. We had a relaxing and enjoyable sail. Worth the cost.

Date of experience: June 2018
Thank cynthiasT218QV
duskyjeff, Owner at Lady Patty Sail Charters, responded to this reviewResponded June 20, 2018

That is awesome! I'm glad you enjoyed it. Thank you for your business and for the kind words. Cheers! -Jeff

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Questions & Answers
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May 28, 2018|
Response from duskyjeff | Property representative |
Hi, Thanks for your interest in the Lady Patty! The cost would be 50 per person. It's probably best to make a reservation at least a week prior to your desired sail time. Hope to see you then. Cheers! Jeff
pat m
April 18, 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