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Sweep your partner off their feet with a private two-hour charter on Epiphany, a 44-foot catamaran that turns the Chesapeake Bay into your personal stage. Intimate, elegant, and easy to customize—this proposal cruise from St. Michaels Sailing Charters is tailor-made for unforgettable yeses.
Sweep your partner off their feet with a private two-hour charter on Epiphany, a 44-foot catamaran that turns the Chesapeake Bay into your personal stage. Intimate, elegant, and easy to customize—this proposal cruise from St. Michaels Sailing Charters is tailor-made for unforgettable yeses.
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Operated by St. Michaels Sailing Charters · Saint Michaels, Maryland
On the water, with the rattle of the rigging and the hush of open bay, St. Michaels becomes a stage for one of the most intimate proposals you can imagine. The Marriage Proposal Engagement Cruise on Epiphany departs from Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663, and sets a private course across the Chesapeake Bay for two hours aboard a modern 44-foot catamaran called Epiphany, operated by St. Michaels Sailing Charters. Designed for six or fewer guests, this package combines low-key luxury—complimentary champagne for guests 21 and over—with a captain and crew focused on timing, scenery, and discretion. The scene is Chesapeake Bay: tidal flats, oyster beds, marsh grass, and a wide-open horizon framed by steeple-tops from the town’s waterfront. Unique geological features include the bay’s shallow estuary and the salt marshes that cradle St. Michaels’ shoreline; look for the rippled sandbars and the wooden piers that attest to generations of boatbuilding and crab-fishing. Wildlife regularly seen on these runs includes bald eagles perching over shallows and diving osprey; close encounters with calving dolphins are uncommon but possible. St. Michaels itself is a compact historic port with clapboard houses, the Chesapeake Bay Maritime Museum nearby, and a maritime legacy dating to the 18th century. Proposing here ties your moment to local culture: boatyards, skipjacks, and the lingering smell of salt and cedar. Because the boat holds only six people, couples can plan surprise guests or keep it strictly private; the crew will help position the vessel for the best light and a sheltered swell. Practical notes: arrive 15 minutes before departure at the Harbour Inn & Marina dock. The cruise runs two hours, pricing starts at $895 plus taxes and crew gratuity. The package is ideal in spring through fall when seas are calmer; winter charters may be available by request. Bring a jacket—the bay runs cooler than land—and a portable battery for cameras. Champagne service is restricted to those 21 and over. Why book this over a waterfront picnic? A private charter shifts the backdrop from predictable parkland to something cinematic: endless water, shifting sky, and the small human drama of a proposal made away from crowds. For travelers staying in nearby Annapolis or Oxford, a short drive delivers an experience that feels both local and singular—a proposal arranged on your schedule, framed by the elemental drama of the Chesapeake. Book early during summer weekends to secure sunset slots, or choose a midweek morning for softer light and calmer water. The captain can anchor in a quiet cove for photos and private toasts; you can customize signage or bring a photographer. St. Michaels Sailing Charters coordinates with local florists and photographers on request for seamless planning.
easy.
2 hours.
Minimal physical exertion—suitable for most fitness levels; be able to board a small yacht from a marina dock.
The Epiphany holds a maximum of six guests, making it suitable for an intimate two-person proposal or a very small private celebration.
Check in 15 minutes before departure at Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663; the vessel departs from the Harbour Inn & Marina dock.
Complimentary champagne is provided as part of the package for guests 21 and over; additional requests should be arranged with the operator ahead of time.
The cruise lists a minimum age of 18 in structured details; contact St. Michaels Sailing Charters to confirm any exceptions or family accommodations.
Charter operators will monitor conditions and may reschedule or advise alternatives; contact the provider directly for last-minute weather policies.
Yes—many couples bring a photographer or light decorations; coordinate details with St. Michaels Sailing Charters in advance so the crew can help stage the moment.
St. Michaels has deep maritime roots dating to the 18th century and is home to the Chesapeake Bay Maritime Museum, which highlights regional boatbuilding and watermen culture.
The Chesapeake Bay faces ongoing restoration efforts—local charter operators typically follow best practices like avoiding sensitive seagrass beds and minimizing single-use plastics to reduce impact.
St. Michaels Sailing Charters operates private catamaran charters from Saint Michaels, Maryland, offering on-water experiences aboard Epiphany, a Leopard 44 catamaran. The company provides private Sailing Catamaran Charters for groups up to 13 people, departing from St. Michaels harbor. Trips focus on relaxed sailing, scenic views of the harbor and tributaries, and private dining or social time on deck. St. Michaels Sailing Charters presents a single primary offering described as the "Private Sailing Catamaran Charter - Up to 13 People." This trip features an open forward cockpit and covered deck spaces on Epiphany, allowing guests to enjoy fresh air and unobstructed views while remaining sheltered if needed. The charters are staged from Saint Michaels, Maryland, a harbor town on Maryland’s Eastern Shore known for maritime activity and waterfront attractions. The operation emphasizes private bookings aboard a defined vessel and accommodates groups up to the listed capacity. Information presented focuses on the vessel type, passenger capacity, departure location, and the experiential highlights of sailing and dining on the water. Third-party references or booking platforms may provide schedules, rates, and availability for the Private Sailing Catamaran Charter offered in Saint Michaels, Maryland.
Book with St. Michaels Sailing Charters