Tag Archives: sailing charters

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


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.


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


Sailing charters departing 3 times daily for the open Chesapeake Bay from Tilghman Island near St Michaels, Easton and Oxford on Maryland’s Eastern Shore

Hello travelers,

Welcome to ladypatty.com, your guide to classic yacht sailing on the Chesapeake Bay.

It’s hard to imagine a better weather forecast for this coming holiday weekend and you should take advantage of it with a sail aboard the 1935 built classic Lady Patty! Our trips are very popular and often sell out early so don’t wait too long to secure your spot.

Check availabilty and buy your tickets here!

We are offering three public charters daily throughout this week and weekend starting on Wednesday. Check out the daily weather and trip availability to plan your excursion.


  • Mimosa Morning Sail 10AM – 12PM offers cooler temps and fewer people. $40 per person
  • Afternoon Sail 1PM – 3PM, sunny and warm, perfect for a cold beer or margarita $40 pp
  • Private Sail 3:30 – 5:30 is set aside for private charters. Call the Captain to schedule a private charter for just you and yours at 410.886.1127.
  • Champagne Sunset Sail 6PM – 8PM full drink service, cooler temps, complimentary champagne and a beautiful Bay sunset. $50 pp…Cheers!

Wednesday 8/27-Sunny, high temp of 83, winds 5 knots from the South Southeast shifting to IMG_0847

Southwest late. 

Thursday 8/28Sunny, high of 79, 10-12 knots of wind from the North

Friday 8/29-Sunny, high of 79, 5-8 knots of breeze from the North to the Southeast late in the day. 

Saturday 8/30-Sunny and a balmy 83 with 6-12 knots from the South

Sunday 8/31-Sunny, high temp of 84 with 8-10 knots from the South

Monday 9/1Happy Labor Day!!! Mostly sunny, winds 8-10 from the South, chance of T-storms


We still have a few sails open for Private Charter at all four sail times this weekend. Call soon to discuss the details with Captain Jeff soon before they all book. 410.886.1127

Check availability and buy your tickets here!

Thanks for checking out the classic yacht Lady Patty! We look forward to welcoming you aboard…Cheers! – Jeff

Sailing charters departing 3 times daily for the open Chesapeake Bay from Tilghman Island near St Michaels, Easton and Oxford on Maryland’s Eastern Shore


Classic yacht sailing charters on the Chesapeake Bay aboard Lady Patty

IMG_0897smallHello travelers,

This weekend is shaping up to be the perfect time for classic yacht sailing charters on the Chesapeake Bay aboard Lady Patty but we are booking up quickly. Check out the times, weather and availability below.


Friday 6/13 – Private all-day charter. Sorry, no public ticket sales.

Saturday 6/14Mostly sunny, high temp of 76, wind 10-15 knots  from the West Northwest clocking North late in the day.  

Morning Sail 10-12-We still have plenty of room on this trip but the phone is ringing…book soon!

Afternoon Sail 1-3 –No more tickets available.

Champagne Sunset Sail 6:30-8:30 –No more tickets available.

Sunday 6/15Sunny & Clear, high of 76, wind from the Northwest at 5-10 knots. Perfect weather for sailing!!!

Mimosa Morning Sail 10-12 –We have plenty of room aboard this trip….join us.

To check for availability or to buy your tickets online go to the “Public Sailing” page on ladypatty.com.

Thanks for checking us out at ladypatty.com.


jeff signature med



Early Spring Update from Lady Patty


Hello travelers,

Spring is coming my friends so hold on a little longer!

We will be finishing a pretty major deck job on the ol’ girl as the weather warms up so we probably won’t be open for charters until later in April.

We are excited about 2014 and believe it will be a banner year for Tilghman Island and Lady Patty. E-tickets are available now under the public sailing tab. You should start making your plans now to join us for a real sailing experience aboard an amazing old yacht out on the beautiful Chesapeake Bay!

I look forward to sailing with you.


jeff signature med

The TAYA Tilghman Island Kayak Rally – August 25th 2013

The Tilghman Area Youth Association is hosting a Kayak Rally on August 25th to benefit this program.  If you know any local kayak enthusiasts or paddle boarders and could forward this message we really would appreciate your support.

The kayaks launch from the Tilghman On Chesapeake Yacht Club at 11:00 on Sunday Aug 25th and paddle 2.5 miles to the Black Walnut Point Inn for a picnic style lunch.  We provide transportation back to the Yacht Club, or experienced paddlers can continue on and circumnavigate the Island.  Rental kayaks are available if reserved in advance and there is also a lunch only option.  Everyone needs to pre-register by Aug 20th.

As a thank you to participants, Lady Patty is giving coupons for 25% off of our ticket price for specially scheduled charters. We have the following trips available for the participants to redeem their coupons:

09/01/2013 – Sunday Morning Sail 10:00-12:00 $35.00 per person ($26.25 after discount)

09/15/2013 – Sunday Morning Sail 10:00-12:00 $35.00 per person ($26.25 after discount)

10/17/2013 – The Great Chesapeake Bay Schooner Race  8:00AM until early afternoon $80.00 person ($60 after discount)

Get more information or redeem your coupon here or by calling 410.886.1127.

Schedule Update for the week of 8/5 – 8/11

friends of LPHi travelers,

The forecast doesn’t include much sun but don’t let that keep you from  getting out on the water. The chance of rain is light to moderate throughout the weekend but the wind is strong and steady. If you are looking for adventure and  a vigorous sailing experience, this is the time! Lady Patty loves a big breeze! Join us!

We will be sailing at our usual times this week with a limited schedule on Sunday. We will be offering a Morning Sail from 10-12, an Afternoon Sail from 1-3 and our ever popular Champagne Sunset Sail from 6:30-8:30. Tickets can be purchased online here or by calling us at 410.886.1127.

Thursday (8/8) – Partly cloudy with a chance of rain . High of 82F with a heat index of 88F. Winds from the South at 10-20 knots.

Friday (8/9) – Partly cloudy with a chance of rain. Wind 10-20 knots from the SSW, high temp of 86F.

Saturday (8/10) – Partly cloudy with a slight chance of rain and thunderstorms, wind 5-15 knots West shifting NNW later, temps near 82F. This should be the best sailing day of the weekend!

Sunday (8/11) – Overcast in the morning, then partly cloudy with a chance of a thunderstorm and rain. High of 82F with a heat index of 88F. Winds from the East at 5 to 10 knots.

Thank you for checking us out! We look forward to welcoming you aboard the classic yacht Lady Patty.


Lady Patty, Out


Lady Patty on Tripadvisor





Hello travelers,

We have had some BEAUTIFUL weather that has made for some fantastic sailing and that seems to have resulted in some incredibly kind reviews on Tripadvisor so to all of our friends who reviewed us, thank you. Your kind words have made us the highest rated charter sailboat on the Chesapeake Bay!

We try to provide our guests with a personal and memorable experience and the recent reviews make me feel like we are doing something right. Again, thank you.

We are very excited about late summer sailing and if 2013 is like my previous years on the bay, it promises some perfect conditions for an old racing yacht like Lady Patty. As you may know, she is not a light air boat. She really starts to come alive as the wind blows and that’s what we can expect from our late summer and fall seasons.

We really appreciate our guests spending their time with us and hope we can continue to provide them with an “All 5s ” sailing experience that they will remember for years to come.



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 click here or call us at 410.886.1127.

We look forward to welcoming you aboard the Lady Patty.


Lady Patty, Out