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Toast on the Chesapeake with a private two-hour sail aboard Epiphany—champagne, coastal views, and intimate celebration from the Harbour Inn dock in Saint Michaels. Perfect for small bachelorette or bachelor gatherings that want a polished, private waterfront moment.
Toast on the Chesapeake with a private two-hour sail aboard Epiphany—champagne, coastal views, and intimate celebration from the Harbour Inn dock in Saint Michaels. Perfect for small bachelorette or bachelor gatherings that want a polished, private waterfront moment.
Book with St. Michaels Sailing Charters
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Operated by St. Michaels Sailing Charters · Saint Michaels, Maryland
On the water of Chesapeake Bay, a private two-hour charter transforms a hen or stag celebration into something cinematic. The Bachelorette Bachelor Party Cruise on Epiphany launches from Saint Michaels, Maryland, offering intimate sails for up to six guests aboard Epiphany, a modern 44-foot catamaran. Departures are from Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663; guests should arrive at the dock 15 minutes before their scheduled departure.
This short cruise is designed around conviviality and coastal scenery. As the catamaran slips past historic wharves and tidal marshes, the crew pops a bottle of champagne so you can toast against a backdrop of low, glassy water and distant sailboats. The setting highlights Chesapeake Bay’s broad estuary—salt grasses, channel markers, and the payoffs of wide, open sky that make every photo feel editorial. Small groups mean private conversations, curated playlists, and room to move on deck without feeling crowded.
The Epiphany is offered as a private charter, with a maximum of six aboard for this experience and bareboat options for larger private charters up to 13. This is an ideal choice for groups who want to celebrate without bar lines or scene changes, for proposals that feel cinematic, or for people seeking a refined coastal moment before a wedding. The cruise balances relaxation with motion: there’s enough sailing to feel the wind and watch the rigging sing, but the itinerary keeps things easy and approachable for first-time sailors.
Practical notes: the charter starts at $895 plus applicable taxes and crew gratuity; guests must be 21+ to consume alcohol. Bring layered clothing for breezy afternoons, sun protection, and a camera. While two hours sounds brief, thoughtful timing around sunset or the late-afternoon light can make the cruise linger in memory.
Local context matters: Saint Michaels is a longtime Chesapeake boating hub with seafood piers, maritime museums, and working waterfronts that narrate the region’s oyster and shipping history. Choosing a private sail here supports small-boat operators who steward these waterways and offer direct access to the bay’s living landscape. For anyone seeking a splash of ceremony without the fuss of a formal venue, this private Epiphany cruise delivers a compact, luminous escape that centers celebration on wind, water, and close company.
Book early for weekend summer dates and consider a late-afternoon slot to catch softer light; private charters book quickly during peak season. The crew manages lines and navigation so no sailing experience is required, but mobility on deck helps when stepping aboard. This format makes the cruise accessible for friends who want a private moment without the logistics of a land venue. Confirm guest list and dietary needs in advance so the crew can prepare and arrive ready to celebrate.
Check-in is at Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663; arrive 15 minutes early.
This experience seats up to six guests; bareboat or larger private charters can accommodate up to 13.
Champagne is served as part of the celebratory experience; confirm with the operator about additional refreshments.
No prior sailing experience is required; the crew handles navigation and lines.
Guests must be 21+ to consume alcohol on this charter.
Cancellation terms are provided at booking; confirm the specific policy on your reservation page.
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