Half-Day Private Sail on Lady Patty

A Half-Day Private Sail from St. Michaels MD

Explore the St Michaels area of Chesapeake Bay. Join St. Michaels Sailing Charters on our 1935 ketch sailboat Lady Patty for a private 4 1/2 hour day sail that is bound to have everyone smiling ear to ear!

We begin by departing the dock and taking a brief harbor cruise, offering beautiful waterfront views of St. Michaels before heading out onto the Miles River. Once there, we raise the sails and let the wind guide our journey. To enhance your experience, we partner with local businesses to provide custom, pre-ordered food options that can be ready and waiting when you arrive.

Lady Patty:

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. Chesapeake Bay sailing is renowned for its stunning scenery and unforgettable sunsets. 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 is docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland—a charming Eastern Shore town known for its incredible seafood and inviting small-town atmosphere. Whether you’re planning a day trip to St. Michaels or seeking a sailing charter on the Eastern Shore of the Chesapeake Bay, our relaxing sailboat excursions are conveniently located just 90 minutes from Philadelphia, Baltimore, and Washington, D.C., and only an hour from Annapolis.

You are welcome to participate as a working crew member or simply sit back and relax; we’re here to help you complete your Chesapeake Bay sailing experience!

What to Expect:

Immaculate Sailboat: Our beautifully kept historic sailboat offer a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of Lady Patty, making it the perfect setting for a memorable trip on the water.

Friendly and Experienced Crew: Our friendly, knowledgeable captains and crew make every sail both informative and enjoyable, sharing insights about the area and the art of sailing along the way. Guests consistently praise their expertise and welcoming nature, noting how comfortable and well cared for they feel throughout the trip.

Tranquil Sailing Trip: Take a break from the hustle and bustle of daily life with our peaceful and serene sailing experience. Guests have consistently praised the calming and rejuvenating experience of being on the water, creating the perfect escape from the stresses of everyday life.

Captivating Narratives: Our interesting stories and information about the area and sailing will provide an educational and engaging experience that enhances the trip. Guests have appreciated the captivating narratives shared by the crew, providing a deeper understanding of the area and sailing.

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. This is the perfect cruise for a picnic lunch or catered dinner!

Swag: Our ships store includes custom St. Michaels Sailing Charters embroidered shirts, baseball caps, zip hoodies, tote bags, beach towels, stemless wine glasses, and more.  You can pre-order at checkout or let our crew know you are interested in purchasing a souvenir.

Good to Know:

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!

Attire: Be sure to bring comfortable shoes, cameras, sunhats, and a light jacket in spring and fall. It’s about 10 degrees cooler on the water so plan accordingly.

Safety: Our yachts are exceptionally clean and well-maintained, with all modern safety features (life jackets, VHF etc). Foul weather gear is available in the event of unexpected bad weather.

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.

Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663.  If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boats tie up.

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.

Sailboat Highlights:

Max Passengers:

• Lady Patty carries of maximum of 13 guests.
• The U.S. Coast Guard considers all children (regardless of how small they are or what age they are) to be passengers, and as such, you need to count them in, too. For example, mom, dad, and their six-month-old are three paying guests, not two.

Toilet: Lady Patty is equipped with a small marine head available for emergency use, also located down a short set of steps. We recommend guests use the lobby restroom at the Harbour Inn before boarding.

Accessibility: Getting aboard Lady Patty is easy most of the time unless we have an extremely high or extremely low tide in which case there is a step up or a step down to get aboard. Most of the time the deck is just about the same height as the dock so it’s a simple to walk aboard.  Once on deck, guests can walk forward and sit on the cabin top without any steps or they can step down 2 steps into the cockpit area. Our captains and first mates are there to assist anyone who needs a hand.

Comfortable Seating: Lady Patty offers cushioned seating along each side of the wooden cabin top as well as cushioned seating in the rear cockpit area with the captain.

Minimum Guests: Lady Patty has no minimum guest requirement to book a sail.

Still have questions? ☎ 410-849-9864