Tag Archives: tilghman island sail charters

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


This week aboard the lovely Lady Patty


Hi travelers,

Welcome to ladypatty.com , our little corner of the world wide web. This week I, the Captain of Lady Patty and the CFO celebrate our 14th anniversary with a short get-away to Washington D.C.  We will not be offering trips on Thursday afternoon and Friday morning. We will resume our regularly scheduled trips with our Champagne Sunset Sail on Friday.

Wednesday‘s forecast looks like Partly Sunny High of 77F & Breezy, winds NNW at 10-20 Knots in other words PERFECT!!!We have plenty of room on the afternoon sail from 1-3 and limited space on board for the 6:30-8:30 Champagne Sunset Sail.

Friday evening should be Clear, High of 77F with a light but steady breeze of 6 Knots from the SE. This combination makes for a wonderful night to enjoy an easy sail, a beautiful sunset and the Captain’s fresh-squeezed lime & clementine juice margaritas.

Saturday offers us scattered clouds, High of 77F and 5-10 Knots from the SE. We will be sailing from 10-12 and 6:30-8:30 for our Champagne Sunset Sail. Our afternoon sail is private.

Sunday morning will be partly sunny, High of 77F, SSE winds of 5-10 Knots. We still have plenty of room for you to join us for a sail and a delicious mimosa.

For more information or to buy tickets call 410.886.1127 or click here.
*Note-if you buy tickets by phone or online, please consider saving a tree by not printing your tickets. Your name will be on our list. 

In addition to our regularly scheduled public charters, we also offer private charters for you and your group. Ask us about weddings, bachelor/bachelorette parties and family charters under sail aboard the Lady Patty.

We look forward to welcoming you and your’s aboard.


Lady Patty, Out

This week aboard the Lady Patty

Hello travelers,

The warm weather of a typical Chesapeake Bay July is here and will be with us all week. There is no rain in the forecast and winds should be 5-10 Knots early in the week, building to 10-15 Knots as the week progresses.

Typically it is cooler on the water so hydrate yourself, slather on the sunscreen and find a shady spot under sail aboard one of our two-hour excursions on the lovely Chesapeake Bay.

When it’s hot like this, we recommend either the Morning Sail(10:00-12:00) or Champagne Sunset Sail(6:30-8:30). Note: After making this post we have decided to close all Afternoon Charters this week due to heat. The morning and sunset sails will be far cooler and will sail as scheduled. 

Buy your tickets online here.

We are sailing on Monday and Wednesday through Saturday. This week we will be closed on Tuesday and Sunday. Yes, even boat Captains need the occasional days off.

Emma and Laura will be serving up some wonderful beer, wine and cocktails including our Sunset Gold Margaritas made with fresh-squeezed lime and clementine juice. We are also featuring Treehugger Organic Bianco (white wine) and the ever popular boat drink; the Dark & Stormy made with Gosling Bermuda Dark Rum and Ginger Beer.

On a personal note, I’d like to thank the  bachelorettes for a wonderful Private Charter in Annapolis last Saturday. Cheers on the upcoming wedding! I hope you enjoy a lifetime of smooth sailing together! Also, thanks to M & J! You are some of our favorite guests and we appreciate your many times sailing aboard the ol’ girl.

Thanks for checking out our little corner of this world wide web. I look forward to welcoming you aboard the Lady Patty.


Lady Patty, Out.

Memorial Day Weekend Charters aboard Lady Patty

Ol' LP underway with dinghy in tow by ParkerAhoy all,

Finally, the official kick-off to summer is here and we look forward to welcoming you aboard the classic yacht Lady Patty!

Our trips depart from the beautiful Knapps Narrows Marina on Tilghman Island, just nine scenic miles SW of St Michaels. We have a short motor out of the harbor before we hoist over 1100 square feet of sail and head out onto the historic Chesapeake Bay for a true sailing excursion.

Experience excitement and elegance from  the golden age of yacht racing aboard the winner of the 1951 St Petersburg to Havana Race and veteran of many notable races including the Transpac from San Francisco to Hawaii.

We are offering three trips daily on Friday, Saturday, Sunday and Monday at the following times:

Morning Sail 10:00AM – 12:00PM

Afternoon Sail 1:00PM – 3:00PM

Champagne Sunset Sail 6:30PM – 8:30PM

Come sail away aboard the classic yacht, Lady Patty.


Lady Patty, Out.