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!

Summer of ’18 is here and we can’t wait to get under sail with you! We are very excited and proud to announce that  Lady Patty will be available for charters with former First Mate, now Master Captain Emma Brown sharing time the helm.

If your planning your Summer get-away for 2018 or looking for a gift Certificate as an awesome wedding 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.





The classic sailing yacht departing from Tilghman Island

We have had plenty of April showers and May’s flowers are doing fine. Hopefully the rainy season is behind us and we can get on with a great Summer sailing season. Join us aboard our classic sailing yacht departing from Tilghman Island for an experience that you won’t soon forget!

Sail Times

We are currently offering up to three sailing excursions daily at the following times:

Morning Sail 10AM-12PM $45 pp

Afternoon Sail 1-3PM $45 pp

Champagne Sunset Sail 6:30-8:30ish PM $50 pp

More info and tickets are available online at ladypatty.com/public-sailing

In addition to our public sails, we also offer Private Charters aboard our classic sailing yacht for you and your group. Two-hour sails start at 575 depending on the day and time. Call or email to reserve your Private Charter.

Wedding Charters

We love the wedding season! Consider us for on-board bachelor or bachelorette parties for up to 13 of your closest friends and family. Did you know that we also offer on-board weddings performed by the Captain while under sail. Give us a call to describe your dream wedding charter and let us make it the experience of a lifetime.

We offer a true classic sailing yacht experience! We don’t do canned narratives or motor boat rides. The 1st Mate will hoist over 1100 square feet of sail so we can do what the ol’ girl was built to do. Go sailing! Lady Patty was built in 1935 for offshore racing by M.M. Davis & Son of Solomon’s Island, MD. Later she spent her early life cruising and racing all over the Gulf of Mexico and the Atlantic Ocean. Most noteworthy, she even made a Pacific sail as part of the Transpac Race to Hawaii. In conclusion, you will love the rich story of glamorous ports, hotly contested regattas, battles with the ocean’s fury and more.

Reserve your tickets for our public charters or book your exclusive private charter for just you and yours today!



Let’s go sailing!

Hello travelers,

We have waited out another long Winter and Spring is just around the corner!

Reserve your spot now for the upcoming sailing season. We will be sailing Monday and Wednesday through Sunday morning at our usual times of 10-12, 1-3 and 6:30-8:30.

We would welcome the chance to discuss a private charter for you and your family, friends, co-workers or wedding party! Keep us in mind for all of your special events.

Follow us on Facebook to keep up with our special offers and events.

Come experience the thrill of classic yacht sailing on the beautiful Chesapeake Bay aboard Lady Patty.



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_0941 Don’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!


jeff signature med

Lyon Distilling Co. of St Michaels, MD