Category Archives: Lady Patty Updates

Schedule and event updates

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, 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


We are batting 1000 with Another successful marriage proposal aboard Lady Patty

20140725_202117Last Saturday another young man chose the Champagne Sunset Sail  aboard the classic yacht Lady Patty as his time and place to pop the big question….making 5 knots on a beam reach under towering sails with a fresh-squeezed margarita in hand….and of course she said yes!!

Congrats to you both and cheers to you sir…very well played indeed!





Relax and Recover from the Holiday Weekend aboard Lady Patty

lp3Hello 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



Private charters, public sailing on the Chesapeake aboard Lady Patty

cropped-cropped-img_0791.jpgHello and welcome to, our little corner of the world, wide web!

This week we have pretty typical Chesapeake Bay weather in the forecast with some warm, humid, sunny days as well as a few chances for rain.

We will be sailing at least once a day through the weekdays and Friday then three times on cropped-cropped-wheel-cropped.jpgSaturday offering  private charters, public sailing on the Chesapeake aboard Lady Patty. Check out the days, times and weather below:

Wednesday – Clear, high of 86, wind 8-10 knots from the West. Private charter early, then our Champagne Sunset Sail from 6:30-8:30, plenty of room on that sail.

lp3ThursdayPartly sunny, chance of thunderstorms, high of 81, wind 5-7 from the WNW. We have plenty of room on our Champagne Sunset Sail from 6:30-8:30. Try one of our Sunset Gold fresh squeezed lime juice margaritas…cheers!

FridayHigh of 78 with partly sunny skies, 5 knots of wind from the South, Champagne Sunset Sail 6:30-8:30.

Saturday There is a chance for rain and possible thunderstorms early in the day and afternoon but clearing late in time for our Champagne Sunset Sail. We will offer our Morning Sail from 10-12, Afternoon Sail 1-3 and our always popular Champagne Sunset Sail from 6:30-8:30. There is still room on this trip but because it looks like the best weather of the day it’s booking quickly. Check out our schedule and buy tickets here. 

SundayMostly sunny, high of 78, winds North, 5-7 knots. We have some seats still available on lp-2.jpgour Morning Mimosa Sail from 10-12.

Thanks again for checking us out! I hope you have a wonderful visit to Talbot County on the Eastern Shore.


jeff signature med

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

lp3Hello 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.
  • Friday Mostly 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.




Schedule Update for 05/07/2014

20140506_125718_resizedHello travelers,

As I’m sure you know, this Spring has been very wet and cool. You may also know that we have some pretty big projects underway this year. Once these projects are complete we will be good to go for many years to come….however, we are weeks behind schedule.

I apologize in advance for not being ready to sail yet but the 20140506_105007_resized weather is out of our control. Last week a spot opened in the boathouse so we are in doors and working hard to wrap up our projects. We will be in the water by next week and racing in the Elf Classic Yacht Race on Saturday May 17th. Our regular charters will begin on the following Monday (May 19th).

I appreciate your patience!


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

Cool things happening on Tilghman Island and The Lady Patty

Chesapeake Bay Magazine Oct. 2001 cover photo by Jim Tadder

Chesapeake Bay Magazine Oct. 2001
cover photo by Jim Tadder

Ahoy all,

The forecast calls for Partly Sunny skies, temps in the 70s and steady breezes throughout the late week and weekend. In other words, PERFECT!

Grab a sweatshirt or light jacket and join us for a sail on the historic Chesapeake Bay.

Lady Patty will be sailing Thursday through Sunday morning from now until mid-October. This time of year offers some of the most pleasant sailing of the season so join us at one of the following times:

Morning Sail – 10am-12pm, $35 per adult and $20 per kid (12 or younger)

Afternoon Sail – 1pm-3pm , $35 per adult and $20 per kid (12 or younger)

Champagne Sunset Sail – 5:30pm-7:30pm, $45 per person

You can check availability and buy tickets here.

Thanks for checking us out on this wild world wide web.


Lady Patty, Out

This week aboard the classic yacht Lady Patty

IMG_0897smallHello travelers,

Once again, the mid-week looks questionable but Thursday through Saturday are forecast to be pretty awesome.

Here is what’s happening aboard the Lady Patty. After this week, Lady Patty will only be offering public charters from Thursday morning through Sunday morning. Call 410.886.1127 to discuss private charters for Monday – Wednesday.  Tickets for public charters can be purchased here.

Wednesday- Partly sunny, high of 82F winds South 10-15 knots. We have some room aboard out Champagne Sunset Sail from 6-8. 

Thursday-Partly cloudy with a chance of a thunderstorm and a chance of rain. High of 88F. Winds from the SSW at 5 to 10 mph. Chance of rain 50%. The weather is iffy but if it clears up we will be offering our 6-8 Champagne Sunset Sail.

Friday-Partly cloudy in the morning, then clear. High of 75F. Breezy. Winds from the NW at 10 to 20 mph. Perfect breeze for Lady Patty. We will be offering our Afternoon Sail from 1-3 and the always popular Champagne Sunset Sail from 6-8.

Saturday- Partly cloudy in the morning, then clear. High of 68F. Winds from the NW at 10 to 15 mph. Bring a sweatshirt and join us for a perfect, early fall sail. This is my favorite time for sailing! We have room aboard our Morning Sail from 10-12 however the later two trips are private. There will not be public tickets available.

Sunday-We are not offering sails today. Sorry!

Thanks for checking us out. I hope you enjoy your visit to Tilghman Island.


Lady Patty, Out

Perfect weather for sailing aboard the Lady Patty

..sunset as seen off the starboard beam of Lady Patty Hello all,

It literally doesn’t get any better than this! We have sunny and cool days in the forecast for the remainder of this week. You should take advantage of this perfect WX and  join us for a sail aboard our 78 year old sailing yacht for a two-hour excursion on the beautiful Chesapeake Bay. You can check the schedule or buy your tickets here.

We are offering a Champagne Sunset Sail on Thursday (9/5) and Friday (9/6) from 6-8PM. The cost for that sail is $45 per person and includes complimentary champagne.

We will also be sailing from 10-12 and 1-3 on Friday and 10-12 on Sunday (9/8). The cost for the morning and afternoon trip is $35 per adult and $20 for kids 12 or younger.

While we have plenty of room on all of the above listed trips, we are not available for public charters on Saturday. We have a private charter in Annapolis and will be gone all day.

Thanks to all our guests who have made this the best year yet! We appreciate your business and look forward to welcoming you back aboard as friends!


Lady Patty, Out