Tag Archives: st michaels 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.





Relax and Recover from the Holiday Weekend aboard Lady Patty

lp3 Hello travelers,

I don’t know about you but I need a vacation  after the 4th of July holiday weekend!

Join us on Tilghman Island for a relaxing weekend of great cropped-header1.pngfood, shaded hammocks, afternoon naps and a Champagne Sunset Sail aboard the classic yacht Lady Patty.

We will sail from 6:30-8:30 on both Friday and Saturday and it’s not too late to reserve your spot with us! There is still room on both evening’s trips and also on Sunday’s Morning Mimosa Sail from 10-12.

cropped-cropped-img_0791.jpgTickets can be purchased online here. 

Thanks for checking out the classic yacht Lady Patty on our little corner of the www.



jeff signature med



This week the weather is PERFECT and the sailing will be GREAT!!! Join us!

LP and the Sharpes Island Lighthouse by Jim TadderHello travelers,

The Spring may have been cool and wet but the Summer is pretty spectacular. We have cooler temps and lower humidity than is usual for July and August so we will take full advantage and sail often.

We will be sailing at the following times Wednesday through Saturday with a limited schedule on Sunday. In the event of light bookings for the morning and afternoon sails we sometimes consolidate those two trips.

Morning Sail  10:00 – 12:00, Afternoon Sail 1:00 – 3:00 & Champagne Sunset Sail 6:30 – 8:30. Click here to check availability or to buy your tickets online.

Wednesday 7/31

It will be partly cloudy, high of 82 with a nice breeze of 7-15 knots from the South.

Thursday 8/1

The day is forecast to be overcast with a chance of rain and T-storms, high of 81 and winds 10-15 knots from the South.

Friday 8/2

Clear in the morning becoming partly cloudy in the afternoon. Friday should have perfect sailing breezes with 5-15 knots out of the WNW veering to the SSW late.

Saturday 8/3

High of 82 and partly cloudy. Winds 7-10 knots WNW early then veering to the SW by evening.

Sunday 8/4

Sunday will be partly cloudy, high of 79 with a wonderful 10-15 knots of wind from the NNW.

We will be offering our usual soft drinks and bottled water for sale on board. We also have a great and ever evolving list of libation including craft beers(Mama’s Little Yellow Pils, Dale’s Pale Ale, Ol’ Chub Scotch Ale, Flying Dog’s Atlantic Lager, Brooklyn Brewing Co’s Summer Ale, Blue Mountain Kolsch, Maui Brewing’s Coconut Porter and Sierra Nevada Pale Ale), wine(Treehugger Organic Bianco)and featured cocktails(fresh-squeezed lime juice margaritas and dark and stormys).  Of course champagne is complimentary on out Sunset Sails!

Thanks for checking out our little corner of the world wide web!



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