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3 hours from New York and Philadelphia, 1.5 hours from DC & Baltimore. Minutes from St Michaels, Oxford, Easton, MD on Tilghman Island. The yacht Lady Patty

Hello travelers,

Welcome to LadyPatty.com!

Finally the warm Summer weather has arrived! This a perfect time to get out on the water.

If your planning your Summer get-away or looking for a gift Certificate as an awesome weddingreserve button present, you probably have a lot of questions. Here is the who, what where, when how and why of the classic yacht Lady Patty!

SONY DSCI’m Captain Jeffrey Mathias, owner and operator of the 1935 built offshore sailing yacht Lady Patty. We offer two-hour public sailing excursions and two-hour, half-day and full-day private charters for our guests to experience the magic of varnished teak, polished bronze, towering sails and the wide-open spaces of the Chesapeake Bay.

We are conveniently located just 3 hours from New York and Philadelphia, 1.5 hours from DC & Baltimore. Minutes from St Michaels, Oxford, Easton, MD on Tilghman Island. The yacht Lady Patty is in a perfect spot for our purposes. We motor for 5 minutes to the wide open Chesapeake Bay.

We pride ourselves on offering our guests a true yacht sailing experience. We don’t do harborIMG_1558-2 tours or historic narratives. We hoist over 1,100 square feet of sail and let the ol’ girl loose in her favorite environment.  Whether it’s a relaxing reach in 5 knots of breeze or sailing close hauled to windward in a brisk 15+ we enjoy sailing in its purest form. Of course a delicious boat drink like a fresh-squeezed margarita can help make your trip memorable, too.


friends of LPWhy should you choose a sail aboard the Lady Patty?

Because we think our area of the Chesapeake is one of the best sailing spots in the country. We love sailing aboard the historic yacht Lady Patty and we look forward to sharing this simple but beautiful lifestyle with you.






Wedding Season on the Chesapeake Bay aboard the Lady Patty

Hello travelers,

As you know, late Spring and early Summer are perfect for a destination wedding. Plan your wedding season on the Chesapeake Bay to include a sail aboard the classic yacht Lady Patty now!

Consider an intimate Private Sunset Sail to pop the question. It will be a proposal that will be the envy of all of your friends. We have had eleven proposals in the last five years and our record is perfect with eleven happily married couples.

We love to be a part of a festive bachelor/bachelorette cocktail cruise. These private charters have become very popular for friends to celebrate the upcoming event. We offer drink service on board and can arrange to have food catered by one of our fine, local eateries. We’ll even pick it up and serve it when you’re ready. Margaritas anyone?

Lady Patty is a beautiful setting for the bridal party to toast the newlyweds after the ceremony, Join us for a sail with your photographer to have images of you surrounded by your friends and family,  varnished teak, billowing sails and the natural beauty that is the Chesapeake Bay.

Who wants a limo when you can leave your reception aboard a classic yacht? Sail off into the sunset while sipping champagne with the love of your life.

Whatever type of wedding season excursion you choose, Lady Patty offers her guests a perfect setting for memories and photographs that will be cherished for a lifetime.

You can also see what beautiful Talbot County has to offer for your wedding experience at  tilghmanisland.com, tourtalbot.org and stmichaelsmd.org!

Call Captain Jeff to discuss on board ceremonies or any of the fantastic options described here in. We look forward to being a part of the most important event of your lives!



Memorial Day Weekend Sailing Schedule


Hello all!

Here is a printable jpeg of our sailing schedule for this beautiful weekend.

Keep us in mind if you, your friends or your guests are looking for something awesome to do.



Lady Patty mem day schedule 16


Lady Patty Buy One, Get One Friday Gift Certificate Sale!

IMG_0941Don’t fight the crowds! Shop from home because Black Friday Sales have nothing on the first ever Lady Patty Buy One, Get One Friday Gift Certificate Sale!

Give a gift certificate for a Friday Champagne LP undersailSunset Sail aboard the classic yacht Lady Patty and you will receive one for yourself. Add a fresh-squeezed margarita and you too will enjoy one with my compliments. It’s that easy. Buy two, get two. You deserve it. Treat yourself!

We can mail our special Holiday Gift Certificate directly to the recipient or email it to you so you can personalize it and send it yourself.

IMG_0847Is there a better way to warm the heart of a colleague, friend or family member than the promise of a summer evening under sail, champagne and hopefully a breathtaking sunset aboard a 1935 racing yacht?

The answer is yes, when you get one too!!!

For more information contact me by phone or email.



We still have some spots open for this weekend..

… aboard the classic Lady Patty so check out our schedule and buy your tickets here! Aside from the usual Chesapeake Bay summer time chance of a T-storm, the weather forecast looks great!


We only have two spots left for Friday evening and 4 for Saturday evening. If you are interested in a beautiful Champagne Sunset Sail aboard our classic yacht, click here.


Father’s Day Weekend aboard the Lady Patty

lp for rack card

Hello travelers,

Are you looking for a great way to spend some time with the dad in your life?

You should join us for a sail aboard the 1935 built 45′ classic sailing yacht Lady Patty for a sail on the wide open Chesapeake Bay! 

We will be sailing up to three times daily from Thursday until Monday at the following times:

Morning Mimosa Sail 10AM – 12PM, $40 per person

Afternoon Sail 1PM – 3PM, $40 pp

Champagne Sunset Sail 6:30PM – 8:30PM, $50 pp includes champagne and a beautiful sunset on the Bay

Experience the elegance and thrill of yards of varnished teak, polished bronze and over 1100 IMG_0897small square feet of sail towering overhead.

Call us at 410.886.1127 or buy your tickets online at ladypatty.com!

We look forward to sailing with you.





Father’s Day Weekend aboard the Lady Patty

Lady Patty is back in business and better than ever!

Fall sailing on the Chesapeake Bay aboard the classic yacht Lady Patty. Available for private charters and public sailing from Tilghman Island, MarylandHello all,

As some of you may know, the Lady Patty  suffered some damage to her mizzen mast and rigging over the Memorial Day Weekend! I know, right? That’s a heck of a way to start off her 80th year in existence. The great news is that the meticulous repairs over the last two weeks has returned her to her usual safe, able and sea-worthy status as the longest operated charter sailing yacht in Talbot County!

Join us this weekend to beat the heat in the coolest way possible; under 1100 square feet of sail with a fresh-squeezed margarita in hand on the wide open and beautiful Chesapeake Bay.

We have plenty of room on our Friday Champagne Sunset Sail and on all three trips on Saturday(10-12, 1-3 and 6:30-8:30). There is still room on the Sunday morning Mimosa Sail from 10-12. Buy your tickets here  or call our office at 410.886,1127. We’ll answer any questions that you might have then sign you up for a wonderful sail aboard the classic yacht, Lady Patty!

Ask us about our reduced kid rates and our military, law enforcement and fire fighter discount.

I look forward to sailing with you.





Sail from Tilghman Island on the Chesapeake – Lady Patty


We’ll be back up and running soon!

Unfortunately, Lady Patty suffered some damage to her rig over the Memorial Day weekend. The good news is that repairs are going well and we will be back in operation by Friday the 12th of June.

The bad news is that we are closed for business this weekend.

I hope you’ll be patient while we return LP to her usual safe and fully operational status.


Lyon Distilling Co. of St Michaels, MD

Funnel_LyonDistilling_02Hello travelers,

The chilly wind and frigid temps have me thinking about Spring and with Spring comes sailing and with sailing comes boat drinks aboard the yacht Lady Patty!

We are very excited that our 2015 season will feature the spirits of Lyon Distilling Company including their rums, rye whiskey and moonshine, depending on what Ben and Jamie release that week. Like most hand-crafted small20140917_190252 batch liquors, the quantities are limited so the drink menu will be as they say, fluid.

If you like good hand-made Rum and love to support  small, local businesses, check out their new website or show them a little love on the Facebook.

I’m going to spill a little of their caramel Rum in my coffee, join the dog in front of the fire and leave you with a heart-felt cheers.

So, cheers!


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Lyon Distilling Co. of St Michaels, MD


The Lady Patty is a charter sailing yacht departing from Tilghman Island, Mayland for the beautiful Chesapeake Bay

Perfect weather for sailing on the Chesapeake Bay! Departing three times daily from Tilghman Island, near St Michaels, Oxford & Easton on MD’s Eastern Shore

Mizzen sail at sunset from the deck of the classic charter yacht Lady Patty near Tilghman Island on the Chesapeake BayHello travelers,

The forecast calls for perfect weather for sailing on the Chesapeake Bay! Departing three times daily from Tilghman Island, near St Michaels, Oxford & Easton on MD’s Eastern Shore, Lady Patty is available for two-hour public sails at the following times:

  • Morning Sail 10AM – 12PM
  • Afternoon Sail 1PM – 3PM
  • Champagne Sunset Sail 5PM – 7:15PM

While Thursday is blustery and wet, the remainder of the week looks absolutely perfect for a sail aboard the 1935 built Lady Patty. Check out the following schedule with weather and trip availability for the weekend:

Friday 9/26 – Sunny and clear, high of 73, wind from the Northeast at 8-10 knots, perfect!!! We have The sailing charter boat Lady Patty transitting Knapps Narrows under the drawbridge to Tilghman Island at sunset plenty of room on both the Afternoon Sail and the Champagne Sunset Sail…fresh-squeezed lime juice margarita for ya???

Saturday 9/27 – Sunny, high of 75, wind NE at 6-8 knots.We have 13 spots available on the Morning Sail, and a few spots left for the Champagne Sunset Sail but the Afternoon Sail is booked up. Reserve your spot soon while there are still tickets available!

Sunday 9/28 – Sunny, 76, winds light at 4-6 knots from the NE, enjoy a quiet Morning Sail and a Mimosa. 9 tickets available. Lady Patty will be closed for the remainder of the day.

20140922_134610Sarah, the First Mate will take excellent care of you while underway. She knows a lot of history about the Bay and the boat. She also is your hook up for bottled water, soft drinks, craft beer, wine and her awesome featured cocktails, all of which are available for purchase on board. Here is Sarah enjoying another amazing day at the office on the beautiful Chesapeake Bay! Can you tell she loves here job?

Join us for a sail during your visit to Talbot County and see why we have received all 5s on Tripadvisor! We love this stuff and we hope you will, too!


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Perfect weather for a sail aboard the classic Lady Patty

Lady Patty on a Chesapeake Bay Champagne Sunset Sail Hello travelers,

This weekend we have plenty of room on all of our two-hour sailing excursions and the forecast calls for perfect weather for a sail aboard the classic Lady Patty.

We will be sailing on the Bay at the following times”

  • Morning Sail 10AM – 12PM
  • Afternoon Sail 1PM – 3PM
  • Champagne Sunset Sail 5PM – 7:30PM

Check out the trip schedule and weather forecast below:rack card

  • Thursday 9/18 – Sunny and mild, high of 74, wind 2-5 and variable. We have plenty of room on all three trips. The weather is perfect for those looking for a quiet and relaxing sail.
  • Friday 9/19 – Sunny, high temp of 72, winds 10-12 from the East, perfect sailing breeze for LP but with very little sea action. Join us on any of the three times.
  • Saturday 9/20 – Sunny, 72, wind South at 5-10 knots, there is still some room on all three trips but they are going fast. Book soon!
  • Sunday 9/21 – Sunny, 76, wind from the Southeast at 5-7 knots. We will be offering our Mimosa Morning Sail from 10-12, plenty of room. Finish off your weekend with a gorgeous sail!

I hope you enjoy your time on the Eastern Shore and I hope to see you on board the classic yacht Lady Patty!


jeff signature med