Tag Archives: tilghman island sailing charters

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!

Spring of ’18 is near and we can’t wait to get back 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.





4th of July Weekend aboard the classic yacht Lady Patty

Ol' LP underway with dinghy in tow by ParkerHello travelers,

Thanks for checking out the Lady Patty!

We have some great weather forecast for our weekend and as a result we only have limited space left on our excursions.  Here is what we still have available as of Thursday afternoon.


Sorry! No seats available.


  • Morning Sail10:00-12:00, 3 seats left.
  • Afternoon Sail1:00-3:00, 7 seats left
  • Champagne Sunset Sail6:30-8:30, sorry! No seats available


Morning Sail10:00-12:00, 13 seats left

Check the current schedule and buy your tickets online here.

Thanks again…cheers!

jeff signature med

This week aboard the classic yacht Lady Patty 5/28/2014

lp3 Hello travelers,

We had a perfect Memorial Day weekend and look forward to more of the same this coming weekend. Join us for Chesapeake Bay sailing charters departing three times daily from Tilghman Island. On board drink service this week will include a great list of craft beers, champagne and two featured cocktails; our fresh squeezed lime-juice margaritas and Lady Patty Lemonade made with Tito’s handmade vodka and fresh lemons.

Check out the forecast and charter notes below when planning your week’s activities.

Weather Forecast:

  • TodayWarm, humid with a chance of thunderstorms in the evening. Hi 79 We have a Champagne Sunset Sail on the books with plenty of space. Hopefully the WX will cooperate. 
  • ThursdayCooler, Hi of 61, partly cloudy with a chance of rain all day.
  • FridayMostly sunny, 70, light variable wind from the North. Lighter winds make for relaxing sails. We have some tickets still available for our Sunset Sail
  • SaturdaySunny and clear, temps in the low 70s, wind North becoming East by evening 10-15 knots. Lady Patty loves a good breeze. If you are looking for a more vigorous sail this is your day. We have plenty of space on all three trips.
  • SundayClear, Hi of 72, winds 8-10 knots Northeast becoming South by evening. Join us for a Mimosa Morning Sail from 10-12

You can check the schedule and buy your tickets online here.

Join us to experience why 55 Tripadvisor reviewers have given us all 5s!

We look forward to hearing from you. Thanks for checking out our little corner of the world wide web.




Weekend Schedule and WX forecast 7/25 – 7/28

cropped-cropped-lp81.jpgThe forecast for Tilghman Island this weekend looks great with cooler temps, nice breezes and partly-sunny to partly cloudy skies. Click here to buy tickets!

Thursday 7/25 

Mostly cloudy, cool and breezy. Winds NNE 10-20 knots. That’s Lady Patty’s kind of wind. 

Morning Sail 10:00  – 12:00Currently plenty of room on this trip.

Sorry, no afternoon sail today.

Champagne Sunset Sail  6:30 – 8:30 – There is limited space on the evening trip so book soon if you are interested. It should be a great, spirited sail. 

Friday 7/26

Partly cloudy in the AM then clear as day progresses. Wind N vearing West late 5-15 knots. 

Morning Sail – 10:00 – 12:00  Plenty of room at this time.

Afternoon Sail 1:00 – 3:00Plenty of room at this time.

Champagne Sunset Sail 6:30-8:30This trip is full. There are no tickets available for purchase.

Saturday 7/27

Partly to mostly cloudy, slight chance of rain. Winds 5-10 knots from the West shifting to ENE late.

Morning Sail – 10:00 – 12:00   As of Thursday morning there are only 6 tickets available. Book soon if you are interested in this trip.

Afternoon Sail 1:00 – 3:00 Plenty of room at this time.

Champagne Sunset Sail 6:30-8:30 This trip is full. There are no tickets available for purchase.

Sunday 7/28

Morning Sail 10:00 – 12:00Plenty of room at this time.

Weekend Schedule and Weather

Happy Independence Day Weekend from Lady Patty Classic Yacht Charters!!!


The forecast is shaping up and we still have space aboard all of our charters this weekend. We are offering a Morning Sail from 10-12 ($35pp), an Afternoon Sail from 1-3($35pp) and our ever popular Champagne Sunset Sail from 6:30-8:30($45pp). We will sail all three times on Thursday, Friday and Saturday and the Morning Sail on Sunday.  Buy your tickets online here!


Thursday 7/4 – Partly Cloudy and Breezy, wind 10-20 knots from the South, slight chance of T-storms in the late afternoon or early evening. It should be clear by our Champagne Sunset Sail…we still have space aboard.

Friday 7/5 – Partly Sunny and breezy, wind 10-15 knots from the South by Southwest. There is no rain in the forecast and plenty of room on all three trips.

Saturday 7/6 – Partly Sunny and breezy, wind 8-12 knots from the Southwest. There is no precipitation expected. We have room aboard the Morning Sail and Afternoon Sail but the Champagne Sunset Sail is filling up. You should book your spot soon! To check availability and to book your spot clickhere or call us at 410.886.1127.

We look forward to welcoming you aboard the Lady Patty.


Lady Patty, Out


Complimentary Mimosas for Moms – Mother’s Day Weekend Sailing Schedule

Does your mother like sailing? Has she ever been sailing? This weekend is shaping up to have the perfect weather for a sailing charter on the beautiful Chesapeake Bay.

We are honoring our favorite ladies on their special weekend with mimosas aboard the classic yacht Lady Patty compliments of the Captain.

We are sailing from 1-3pm and 6-8pm on Saturday and from 10am-12pm on Mother’s Day.

There is still room on all of the weekend’s charters and for lunch and dinner next door at Mike & Eric’s Bay Hundred Restaurant. Call them at 410-886-2126 for restaurant reservations or 800-979-3370 for charter reservations.

Happy mother’s day….and cheers!

Lady Patty, Out