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.

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  • 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 8/28 Sunny, 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

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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