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Marriage Proposal Engagement Cruise on Epiphany

Raise a glass and take in sweeping Chesapeake Bay views aboard Epiphany, our spacious and modern catamaran, during an unforgettable engagement proposal.

Quick Details

Private Charter

$ 895

Your Proposal Experience

Step aboard Epiphany and sail from the charming harbor of historic St. Michaels onto the scenic Miles River and Chesapeake Bay. With her wide beam and spacious deck, you’ll enjoy panoramic water views, gentle breezes, and a relaxed, intimate setting for your special moment.

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, Epiphany provides a luxurious, private backdrop that makes the occasion truly unforgettable.

Couple standing on a sailing catamaran with colorful sails at sunset.

What Guests Love

  • Luxurious Setting: A spacious, modern catamaran designed for comfort, socializing, and panoramic Chesapeake Bay views.

  • Private & Romantic: Ideal for proposals or intimate celebrations with close family and friends.

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

  • Scenic Chesapeake Views: Glide past historic waterfront landmarks and enjoy sweeping Bay vistas.

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

A diamond ring nestled in coiled green, white, and red rope.

Location

Epiphany 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.

Sunset behind a lighthouse by the water with boats and trees silhouetted.

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:

Logo of Laura's Focus Photography with a sailboat icon.
Website: https://www.laurasfocus.com
Instagram: https://www.instagram.com/laurasfocusphotography
Facebook: https://www.facebook.com/laurasfocusphotography

Couple enjoys sunset on sailboat with colorful sail on calm water.

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:
Epiphany has a private, roomy marine head just a few steps down. We suggest all guests 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 take in sweeping Chesapeake Bay views aboard Epiphany, our spacious and modern catamaran, during an unforgettable engagement proposal. With luxurious comfort, panoramic vistas, and a complimentary bottle of champagne, this cruise creates the perfect setting 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 make it a memory you’ll cherish forever. 🥂

Man kneeling on a sailboat holding a woman's hands under a colorful sail.

Still Have Questions?

We’re happy to help you plan the perfect experience.

410-849-9864
[email protected]

We look forward to welcoming you aboard!