Marriage Proposal Engagement Cruise

Make Your Engagement Unforgettable!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.

Popping the Question

Create an unforgettable proposal aboard one of our private sailing yachts. With the open water as your backdrop, you’ll have the perfect moment to get down on one knee and ask the most important question of your life. Our team is happy to help set the scene with any special, romantic touches you envision.

Celebrate in Style

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

Engagement Photography

Choose to hire a professional photographer to discreetly capture the moment (give us a call and we’ll happily share tips to keep the surprise intact), or let our experienced crew assist by taking photos during your sail. Either way, you’ll have beautiful memories of your proposal to treasure forever.

Our team works closely with you to bring your vision to life, handling every thoughtful detail—from positioning you at the bow of the boat to playing a special song during your private sail—so you can relax and enjoy the moment. We’re here to make your engagement effortless, meaningful, and truly unforgettable.

For professional photography, we recommend Laura’s Focus Photography, who is familiar with both of our sailing yachts and specializes in a nautical, documentary-style approach that’s perfect for capturing this once-in-a-lifetime moment.

Our sailing yachts are 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.

What to Expect:

Immaculate Sailboats: Our beautifully kept sailing boats offer a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of our sailboats, 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: Immediately following the raising of the sails and your proposal, we raise our glasses and toast to you! Your sail includes your choice of:

• Easy-drinking champagne
• White wine: Chardonnay, Pinot Grigio, or Sauvignon Blanc
• Red wine: Merlot, Pinot Noir, or Cabernet Sauvignon
• A rotating selection of icy-cold craft beers from craft breweries
• Non-alcoholic options including water, Coke, Diet Coke, and Sprite
• Bottled water

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.

Choose Your Sailboat:

Choose between our two stunning sailing yachts: the historic Lady Patty, a 1935 Maryland-built ketch, or Epiphany, a spacious and modern 2016 44-foot Leopard catamaran.

Sailboat Highlights:

• Lady Patty offers an authentic monohull sailing experience aboard a beautifully restored 1935 2-masted ketch sailboat. Originally designed for offshore racing, she features original style wooden masts, sails, and rigging.  The captain steers the vessel from the stern and the mate assists by controlling the sails as well as interacting with the guests and serving beverages.  There is ample cushioned seating for all guests, but space and opportunity to lay down or walk around during the sail may be limited. Guest access to the cabin area is limited to emergency use of the head (restroom).
• Epiphany offers a modern, luxurious and spacious sailing experience aboard a wide and stable catamaran intended for charter guest comfort and guest entertainment.  Designed for easy single handed operation, the captain operates the vessel from the helm station allowing the mate to focus most of their time on enhancing the guests experience while aboard.  There is ample cushioned seating for all guests including choices between trampoline, bow pulpit seats, beanbag chairs, captains chairs, built-in shaded cushioned cockpit seating with pillows, inside salon seating, multiple tables and counters for drinks and food, and modern kitchen amenities.

Max Passengers:

• Lady Patty carries of maximum of 13 guests.
• Epiphany carries a maximum of 6 guests (Epiphany is also available for private bareboat charters for up to 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.
• Epiphany features a private and spacious modern marine head (bathroom) located down a short set of steps.
• For both sailboats, 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.
• Getting aboard Epiphany is easy most of the time unless we have an extremely high or extremely low tide. There is usually 1 or 2 steps to get aboard. Once aboard, guests can walk forward to the bow area without any steps, or step down three steps walking towards the aft cockpit seating area.
• On both boats, 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.
• Epiphany has numerous cushioned seating options in shaded front and rear cockpit areas with two dining tables. Guests can also lounge on comfy beanbag chairs or captains reclining chairs on the bow for a front row view of the sail. Guests also love relaxing on the trampoline and can enjoy the view of the water below.

Minimum Guests:

• Lady Patty has no minimum guest requirement to book a sail.
• Epiphany requires a minimum of 2 guests to book a sail. Once a sail is scheduled, additional guests may join with no minimum requirement.

Still have questions? ☎ 410-849-9864