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    Lady Patty Sail Charters

    100 reviews
    #1 of 9 things to do in Tilghman
    Tours, Outdoor Activities, Boat Tours & Water Sports
    Tilghman, MD, USA
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    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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    Show reviews that mention
    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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    1 - 10 of 100 reviews
    Reviewed 1 week ago
    Incredible addition to any day trip or vacation...beautiful vessel

    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
    Made our vacation great!

    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
    Sunset cruise is wonderful

    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
    Anniversary Sunset Cruise

    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
    Captain Jeff & First Mate/Son Jack “ROCK”!

    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
    Great Sail!

    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
    Awesome Time

    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
    Captain Jeff and First Mate Jackson Deserve 5 Stars

    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
    Beautiful sunset sailing experience

    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
    A beautiful trip

    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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    cynthiasT218QV
    May 28, 2018|
    Answer
    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
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    pat m
    April 18, 2015|
    Answer
    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
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