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#1Set on a private 18acre campus with over 2,000 feet of waterfront in St. Michaels, the Chesapeake Bay Maritime Museum offers a beautiful and historic setting for weddings. The venue provides unique spaces like the Small Boat Shed and the Steamboat Building, alongside outdoor areas with spectacular sunset views of the Miles River. It offers a warm, casually elegant Eastern Shore hospitality.
#2Inn at Perry Cabin is a luxury waterfront resort and wedding venue in St. Michaels, Maryland, featuring Colonialinspired architecture, manicured gardens, and views of the Miles River. Couples can host ceremonies on the lawn, in the gardens, on the water’s edge, or aboard the inn’s yacht, followed by elegant receptions in indoor ballrooms or outdoor spaces. Onsite accommodations, dining, and resort amenities create a full weekend experience for guests. Fullservice planning, catering, and bar services support celebrations from intimate micro weddings to large events.
#3Bordeleau Vineyards & Winery is a family-owned estate winery surrounded by 13 acres of vineyards along Wicomico Creek on Maryland's Eastern Shore (the St. Michaels location is one of its tasting rooms). Founded by winemaker Tom Shelton in 1998 with the first vines planted in 1999, the property's name ("The Water's Edge") reflects favorable climate similarities to France's Bordeaux region. The Banquet Room overlooking the vineyard and the Tasting Room each comfortably seat up to 65 guests and are available year-round for bridal showers, baby showers, bachelorette parties, corporate events, and other special occasions. Outside food and catering are welcome, a cash bar is available, only beer and wine may be served in the Banquet Room, and only Bordeleau wines may be served (no outside wine).
#4Miles River Yacht Club is a fullservice waterfront venue located on the Miles River in historic Saint Michaels, Maryland, offering indoor space and outdoor tented areas. Established in 1920, it can host events of up to 150 guests with onsite catering and picturesque marina views. The club’s flexible spaces suit both intimate gatherings and larger celebrations. Its riverside setting provides a relaxed, nautical backdrop for weddings and special events.
#5Sail Selina II, operating under St. Michaels Sailing Charters from the dock behind the Harbour Inn & Marina in St. Michaels, Maryland, offers ceremony-under-sail elopements and micro-weddings on the Chesapeake Bay and Miles River. The fleet features Lady Patty, a beautifully restored 1935 Maryland-built ketch ($1,445 wedding package), and Epiphany, a spacious modern 44-foot Leopard catamaran ($1,345), each accommodating up to 12-13 guests for a private 2-hour sail. A Wharf-Side Wedding aboard Epiphany at dockside hosts up to 50 guests with a 1-hour scenic sail after the ceremony. Packages include a 2-hour private charter, professional captain and crew, complimentary champagne and a personalized ceremony performed by Maryland-ordained officiant Bonnie Brown Scott of Beginnings and Ends. Couples obtain a Talbot County marriage license, and the venue partners with local vendors for photography, florals, cakes, and music.
#6Weddings on a Sailboat is operated by St. Michaels Sailing Charters, departing from the dock behind the Harbour Inn & Marina in St. Michaels, Maryland, and offers intimate ceremonies aboard two yachts: the historic 1935 Maryland-built ketch Lady Patty and the modern 44-foot Leopard catamaran Epiphany, sailing the Miles River and Chesapeake Bay. The Ceremony Under Sail Package ($1,345 on Epiphany, $1,445 on Lady Patty) provides a two-hour private sail for up to 12 guests on Lady Patty or up to 6 on Epiphany, with officiant (Bonnie Brown Scott of Beginnings and Ends), captain and crew, Maryland amusement tax and a celebratory champagne toast; the Wharf Side Wedding Package allows the ceremony to take place dockside on Epiphany with up to 50 additional guests watching from the dock, followed by a one-hour scenic sail. A valid Talbot County marriage license is required, weather permitting policies and rescheduling options apply, and partner vendors are recommended for photography, video, florals, cake, music and rentals.
#7St. Michaels Sailing Charters is a private sailing yacht charter operating from the Harbour Inn & Marina in St. Michaels, Maryland, offering intimate nautical wedding ceremonies, elopements, and vow renewals on the Chesapeake Bay and Miles River. Couples choose between two vessels: Lady Patty, a beautifully restored 1935 Maryland-built ketch with classic wood accents, and Epiphany, a 44-foot modern Leopard catamaran with shaded cockpits, dining tables, and a large trampoline area; each accommodates up to 13 guests under sail (up to 50 dockside on Epiphany). Wedding packages include a 2-hour private sailing experience, professional captain and crew, Maryland-ordained officiant Bonnie Brown Scott of Beginnings and Ends with a fully customized ceremony, complimentary champagne toast, and Maryland State amusement tax (Ceremony Under Sail from $1,345; Wharf Side Wedding aboard Epiphany also available). The charters operate April through November, seven days a week, with the venue ranked TripAdvisor's #1 boat tour in St. Michaels.
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