Marriage Proposal Engagement Cruise

Your Proposal Experience

Set the stage for “yes” with a beautifully scenic cruise departing from historic St. Michaels. After boarding, you’ll glide past waterfront landmarks, feel the refreshing bay breeze, and take in sweeping water views that create the perfect setting for a once-in-a-lifetime moment.

During your 2-hour cruise, a complimentary bottle of champagne is included for your celebration — ready to toast your proposal or newly announced engagement. Whether you’re planning a sunset surprise or sharing the moment together on the water, this sail blends romantic charm with unforgettable scenery.

As you cruise across the peaceful Chesapeake Bay, tranquil waters and harbor views provide a stunning backdrop for candid photos and lasting memories. Our friendly, attentive crew is there to ensure your proposal or engagement celebration feels seamless, intimate, and truly magical. 🥂

Choose Your Vessel

⛵ Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with graceful classic lines, rich wood accents, and traditional rigging that capture the romance of Chesapeake sailing. This timeless yacht creates an intimate, storybook setting — perfect for a heartfelt proposal on the water.

Relax on cushioned seating along the cabin top or settle into the cozy rear cockpit beside the captain — an ideal spot for quiet conversation and the perfect moment to pop the question. Whether you choose a private sunset setting or a celebratory toast after “yes,” Lady Patty offers a romantic, memorable experience that feels both personal and unforgettable.

⛵ Epiphany – Modern Catamaran

Celebrate your once-in-a-lifetime moment aboard Epiphany, a spacious and stable modern catamaran designed for comfort, privacy, and breathtaking panoramic views. With her wide beam and smooth ride, Epiphany offers a relaxed, elegant setting — perfect for a surprise proposal or an intimate engagement celebration on the Chesapeake Bay.

Stretch out on cushioned seating in the shaded front or rear cockpit, sip champagne at one of the dining tables, or sneak away to the bow for a quiet, romantic moment with sweeping water views all around you. Lounge on the forward beanbags or settle onto the trampoline for a front-row seat to the sail and sunset — an unforgettable backdrop for “Will you marry me?”

With plenty of space to move about and a professional crew focused on making your experience seamless, Epiphany provides a private, scenic, and effortlessly romantic setting for the perfect proposal.

What Guests Love

• Champagne Toast Included: One complimentary bottle of champagne is provided for your cruise — perfectly chilled and ready to celebrate your special moment.

• Romantic Atmosphere: Beautiful water views and gentle sails create a perfect setting for proposals and engagement celebrations.

• Comfort & Style: Both Lady Patty and Epiphany offer comfortable seating and scenic vantage points for photos and toasts.

• Friendly Crew: Attentive captains and crew help make your experience smooth, safe, and memorable.

• Waterfront Scenery: Enjoy historic St. Michaels, the Miles River, and wide Chesapeake Bay vistas as part of your celebration.

Location

Our sailing yachts are 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. 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, and Epiphany features a private, spacious marine head. Both are located down a short set of steps. For all guests, we recommend using 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 take in sweeping Chesapeake Bay views during an unforgettable engagement proposal cruise designed for one of life’s biggest moments. With romantic scenery, an intimate setting, and a celebratory champagne toast, this sail creates the perfect backdrop for a heartfelt “yes.”

Reserve your 2-Hour Proposal Cruise today! Popular dates — especially sunset sails and weekends — book quickly, so secure your private moment on the Bay and start planning an unforgettable surprise. 🥂