Marriage Proposal Engagement Cruise on Lady Patty

Your Proposal Experience

Step aboard Lady Patty and sail from the charming harbor of historic St. Michaels onto the scenic Miles River and Chesapeake Bay. As the sails rise and the breeze carries you across the water, you’ll be surrounded by peaceful views, golden light, and the quiet rhythm of classic sailing.

A complimentary bottle of champagne is included — perfectly chilled and ready for your celebratory toast after the big “yes.” 🥂

Whether you’re planning a surprise sunset proposal or an intimate engagement celebration with close family and friends, Lady Patty offers a romantic, private setting that feels both meaningful and unforgettable.

What Guests Love

• Timeless Romance: A classic 1935 wooden sailing yacht with elegant lines and rich wood details.

• Intimate Atmosphere: Perfect for private proposals or small celebratory gatherings.

• Champagne Toast Included: One complimentary bottle provided for your special moment.

• Scenic Chesapeake Views: Sail past historic waterfront landmarks and open Bay vistas.

• Professional Crew: Friendly captains and crew ensure a smooth, seamless experience.

Location

Lady Patty is docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland, a charming Eastern Shore town celebrated for its fresh seafood, historic streets, and welcoming small-town atmosphere.

Whether you’re planning a day trip to St. Michaels or a sailing charter on the Eastern Shore of the Chesapeake Bay, our excursions are conveniently located:

• 90 minutes from Philadelphia, Baltimore, and Washington, D.C.

• 1 hour from Annapolis

Arrive early to explore the quaint town, enjoy local restaurants, or stroll along the waterfront before or after your engagement.

Capture the Moment with a Professional Photographer

A marriage proposal is one of life’s most unforgettable moments. For couples who want to preserve the surprise and emotion forever, we recommend working with a professional photographer to discreetly document the proposal.

Laura’s Focus Photography, based in St. Michaels, Maryland, specializes in capturing authentic, emotional moments through a mix of documentary and fine-art photography. Laura has been photographing weddings and engagements for over 20 years and loves working on the water, making sailing proposals especially memorable to capture.

Whether hidden on board or waiting ashore after the big “yes,” Laura can help capture the moment your partner realizes what’s happening — and the celebration that follows.

If you would like professional photographs of your proposal, we recommend reaching out directly to Laura:

Website: https://www.laurasfocus.com
Instagram: https://www.instagram.com/laurasfocusphotography
Facebook: https://www.facebook.com/laurasfocusphotography

Good to Know Before You Go

Arrival:
Please arrive 15 minutes prior to departure at the dock behind the Harbour Inn & Marina, 101 N Harbor Road, St. Michaels, MD.

Restrooms:
Lady Patty has a small marine head for emergency use, located down a short set of steps. Guests are encouraged to use the Harbour Inn lobby restrooms before boarding.

Parking:
Guests may park in the hotel lot or along the waterfront on Harbor Road past the police boats.

Shoes & Attire:
Wear comfortable shoes or something easy to remove if you prefer to go barefoot. Ladies, please avoid high heels. Light jackets or layers are recommended on cooler days.

Sunscreen & Hats:
If using spray sunscreen, please apply before boarding to protect the varnish. Don’t worry if you forget your sunhat — custom baseball caps are available for purchase onboard.

Weather:
Safety and comfort are our priority. The captain may cancel due to weather, with the final decision made about 15 minutes before departure. There is no charge if a sail is cancelled due to weather, and we will do our best to rebook you, issue a gift card, or provide a refund.

Beverages & Food:
During your 2-hour cruise, a complimentary bottle of champagne is included — perfectly chilled and ready for a celebratory toast as you mark your special moment on the water. We partner with local businesses to offer pre-ordered, charter-friendly food options ready upon arrival. For full details on onboard food and beverage options, please see our policies.

Ready to Set Sail?

Raise a glass and enjoy sweeping Chesapeake Bay views aboard Lady Patty, our beautifully restored 1935 sailing ketch, during an unforgettable engagement proposal. With intimate charm, classic wooden details, and a celebratory bottle of champagne, this cruise sets the perfect scene for a heartfelt “yes.”

Reserve your 2-Hour Proposal Cruise today! Popular dates — especially sunset sails and weekends — fill quickly, so secure your private moment on the Bay and create a memory that will last a lifetime. 🥂