Lady Patty | Saint Michaels, Maryland Sailing

Lady Patty

location_onSaint Michaels, Maryland | Sailing
Out on the open water, our historic 1935 Maryland-built ketch sailboat Lady Patty offers your choice of a public or private cruise in one of the most beautiful places to sail. Limited to just 13 guests.
Starting at $95 per trip
Sailboatkeyboard_double_arrow_up
Lady Patty carries a rich maritime legacy dating back to 1935 when she was built in Solomons Island, Maryland. Originally designed as an offshore racing yacht, she was later restored as a charter sailboat while retaining her original wooden cockpit, wheel, and masts.

This historic ketch accommodates up to 13 passengers and is maintained for both safety and comfort, offering modern-day sailors a unique chance to experience the Chesapeake Bay aboard a true piece of maritime history.

In her early years, Lady Patty raced along the Southern Ocean Racing Conference circuit in Florida, including a notable victory from St. Petersburg to Havana. Her original owner even sailed her through the Panama Canal to San Francisco to compete in the Transpac, a two-week race from California to Hawaii.

Newlyweds On Lady Patty
Newlyweds On Lady Patty (enlarge)
Destinationskeyboard_double_arrow_up
Your charter begins with a peaceful glide through the harbor before heading out into the Miles River, where you'll enjoy sweeping views and, if you're lucky, wildlife sightings like osprey and bald eagles. Several years, we have even spotted dolphins!

Lady Patty At Sunset
Lady Patty At Sunset (enlarge)
Rates & Availabilitykeyboard_double_arrow_up
(All rates in USD $)
From/to April To Nov
LowHighNotes
95pp - 115pp



1200-1600/boat



Starts at $95 per person for weekday day sails

Starts at $95 per person for weekday day sails



Sunset In St. Michaels Harbor
Sunset In St. Michaels Harbor (enlarge)
Amenitieskeyboard_double_arrow_up
Available
  • check Free

General
  • check Reservations Required


Lady Patty Under Sail
Lady Patty Under Sail (enlarge)
Typical Daykeyboard_double_arrow_up
We sail 4 times a day, 7 days a week.

Newlyweds On Lady Patty
Newlyweds On Lady Patty (enlarge)
Age range, type of groupkeyboard_double_arrow_up
Everybody is welcome, no one too young or too old

Wine Tasting Options
Wine Tasting Options (enlarge)
Sleeping and mealskeyboard_double_arrow_up
We partner with local businesses to offer custom, pre-ordered food options that can be ready when you arrive.

Lady Patty At Sunset
Lady Patty At Sunset (enlarge)
Policies & Restrictionskeyboard_double_arrow_up
Beverages: Beer/wine tasting is available as an add-on for 21 and older guests. The beer tasting is an unlimited sampling of 6 Maryland craft beers, the wine tasting is a flight of 3 whites & 3 reds plus a glass of your favorite wine. Or you can simply purchase alcoholic beverages by the glass. Coke, Diet Coke, Sprite are also available for purchase, and bottled water is complimentary.

Food: We partner with local businesses to offer custom, pre-ordered food options that can be ready when you arrive.

Weather: We want to ensure your safety and comfort, hence the captain may decide to cancel due to bad weather, and this decision is made 15 minutes prior to departure. Rest assured there is no charge if the sail gets cancelled. We're often asked whether we sail in rainy weather. We do sail even if it's lightly misting, but not in heavy rain as we want you to have the best experience possible. It's no fun sitting on the pouring rain!

Cancellation Policy:
Per Person Reservations made on a per person basis can be cancelled up to 24 hrs before departure for a full refund.
Private Charters will receive full refund if cancelled more than 7 days prior to start of charter. 50% refund if cancelled less than 7 days and more than 72 hours before start of charter. No refunds if cancelled less than 72 hours before start of charter.

Kid Friendly: Children of all ages are welcome aboard our yachts. We love kids! We have infant, toddler, and youth life jackets to fit all sizes and ages.

Historic 1935 Lady Patty
Historic 1935 Lady Patty (enlarge)
Nearby Attractions and Serviceskeyboard_double_arrow_up
Description Distance
Chesapeake Bay Maritime Museum
0.5
St. Mary's Square
.25
Map & Directionskeyboard_double_arrow_up

101 N Harbor Road, Saint Michaels, Maryland 21663

Points of Interest

Map Pin 1

Lady Patty

101 N Harbor Road, Saint Michaels, Maryland
Host's Infokeyboard_double_arrow_up

Laura Bell
Looking for a relaxing boat tour in Saint Michaels on the Chesapeake Bay? Hoping to get out on the water, unwind, and spend some time in nature? If you’re searching for things to do in St. Michaels, MD or exploring the top local attractions, our luxury sailing yachts—Lady Patty and Epiphany—ar...
View Full Profile

place    
101 N Harbor Road
Saint Michaels, Maryland 21663
United States

person_outline    
Laura Bell
St. Michaels Sailing Charters
101 N Harbor Road
St Michaels, Maryland 21663
United States


Listing # RA-1283242
Updated: Feb 23, 2026 | Viewed 5,275 times.








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