Fall is the perfect time for a Private Charter aboard Lady Patty

The Lady Patty is a charter sailing yacht departing from Tilghman Island, Mayland for the beautiful Chesapeake Bay

Fall sailing on the Chesapeake Bay aboard the classic yacht Lady Patty. Available for private charters and public sailing from Tilghman Island, MarylandThis my favorite time of the year for sailing on the Chesapeake Bay. The weather will only get better as we sail our way through the next couple of month. It’s the perfect time to get your friends and family together for a beautiful excursion aboard the 1935 classic yacht  Lady Patty!

We offer private two-hour, half-day and full-day charters lp-2.jpg for families, friends and corporate groups departing from some of the most beautiful towns on the Mid-Bay. We can sail from our home on Tilghman Island or Oxford, St Michaels, Cambridge, Chesapeake Beach or Annapolis. Call Jeff at 410.886.1127 to discuss your dream excursion to lighthouses, other towns and special events like the Great Chesapeake Bay Schooner Race.

IMG_0897smallPrices start at $475 for an early or mid-day two hours private charter for up to 13 of your closest another beatiful evening aboard the lady patty during a Champagne Sunset Sail on the Chesapeake B friends or family.

We offer drink service on board including bottled water, soft drinks, craft beers and featured cocktails like our fresh squeezed lime juice margaritas, or as the temps cool…hot buttered rum!

Catering is available through some of our awesome local eateries. We’d gladly put you in touch with the right person to discuss your tasty treats.

We look forward to hearing from you. Remember…Fall is the perfect time for a Private Charter aboard Lady Patty!


jeff signature med

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


Saturday – Sunny – Hi 83 – Wind SW 10-15K = PERFECT!!!!

clear It doesn’t get much better than this, folks! Join us for an awesome sail on the wide open spaces of the Chesapeake Bay aboard our 78 year old classic sailing yacht. We have plenty of room on our 10am-12pm morning sail, 1pm-3pm afternoon sail and 6:30pm-8:30pm Champagne Sunset Sail. Call Jeff at 601.307.0398 or go to ladypatty.com to book your spot.


Lady Patty, Out.

Shakedown sail this week then Lady Patty and I are ready for the season!

Hey friends,

The Spring has arrived and we are wrapping up the final preps to be ready for an awesome 2013. The only thing that remains is my solo shakedown sail on the fantastically beautiful Chesapeake Bay.

This has become a cherished ritual for me each spring. I look forward to spending many days underway with some super-cool people but before that happens I go it alone, just the old girl and me. I love the opportunity to listen to the boat-sounds, study the rig and dig the cool relationship a sailing vessel has with the world. There is so much going on with the wind, tide, waves, water, rigging, sails, hull and me. It’s really an incredible relationship. I sometimes get caught up in marketing, bookkeeping, maintaining the boat, managing the crew and watching the forecast and the reason I chose this life slips slightly from the forefront on my mind.

The annual spring shakedown lays it all out in clear and concise terms. I love this stuff! There is nowhere I would rather make my living than healed 35 degrees off normal with a rail in the water, rising and falling with the pulse of the elements, the yacht ensign popping in the breeze, the rush of water on the hull and the excitement of my guests getting their first taste or a welcome refresher of life at 8 knots on a 77 year old sailing yacht.

I still can’t believe I get paid for this!

I hope to see you all when I get back but for now, I have a date.