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This Flag Day, celebrate on the water in a truly once-in-a-lifetime way. St. Michaels Sailing Charters invites you to join us for a special Flag Day Boat Parade Cruise as part of the United States Semiquincentennial — the 250th Anniversary of our nation. This is one celebration you won't want to miss!⚓ WHAT TO EXPECT
🕛 12:00 PM: Depart from the Harbour Inn dock and cruise through the charming harbor of historic St. Michaels, with our boats decorated in red, white, and blue.
🕧 12:30 PM: Meet up with other decorated boats preparing for the parade.
🕐 1:00 PM: The Flag Day Boat Parade begins! Our fleet joins the decorated boats circling the St. Michaels waterfront in a festive, patriotic loop.
🌊 After the Parade: We head out onto the scenic Miles River for a relaxing afternoon sail. Sit back, enjoy the breeze, take in the waterfront views, and toast the occasion with a complimentary glass of champagne! 🥂
Dress in your best patriotic red, white, and blue and come celebrate America's 250th birthday on the beautiful waters of the Chesapeake Bay!
⛵ CHOOSE YOUR VESSEL
Lady Patty – Historic 1935 Sailing Ketch
Step aboard this beautifully restored classic yacht with elegant wooden details that reflect the golden age of Chesapeake sailing. An intimate, authentic, and unforgettable experience.
Epiphany – Modern Leopard 44 Catamaran
Enjoy the parade from our spacious, stable catamaran with panoramic views, shaded cockpit seating, bow lounging, and the famous trampoline deck. Perfect for groups who love comfort on the water.
📅 Saturday, June 14, 2026
🕛 12:00 PM – 3:30 PM
📍 Departing from Harbour Inn, St. Michaels, MD
🎟️ LIMITED SEATS AVAILABLE — Book Now!
🌐 www.stmichaelssailingcharters.com/sailing-trips/flag-day-parade-cruise/
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Event Venue
101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663
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