Special 250th Anniversary Flag Day Celebration Parade Cruise

Your Flag Day Boat Parade Experience

Your afternoon begins as we depart from the Harbour Inn dock at 12:00 PM and cruise through the charming harbor of historic St. Michaels. Step aboard one of our beautiful sailing yachts and become part of the celebration as we decorate the boats in red, white, and blue for the annual Flag Day Boat Parade along the St. Michaels waterfront. This year’s parade is especially meaningful as part of the United States Semiquincentennial—the 250th anniversary of the nation—bringing an extra level of pride and celebration to the day.

At 12:30 PM, we will meet up with other decorated boats preparing for the parade. At 1:00 PM, the Flag Day Boat Parade begins as the fleet circles through the St. Michaels harbor in a festive loop. Guests are encouraged to dress in patriotic colors and enjoy a lively afternoon on the water surrounded by other decorated boats celebrating the American flag.

Both Lady Patty, our beautifully restored historic 1935 sailing ketch, and Epiphany, our modern 44-foot Leopard cruising catamaran, will participate in the parade, giving guests a front-row seat to this unique local event.

After the parade concludes, we’ll head out onto the scenic Miles River for a relaxing afternoon sail on the Chesapeake Bay. Sit back and enjoy the breeze, take in the waterfront views, and experience the joy of sailing during this special holiday celebration. Each guest will receive a complimentary glass of champagne to toast the occasion.

Choose Your Vessel

⛵ Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines and rich wooden details that reflect the golden age of Chesapeake sailing.

This historic yacht offers an intimate and authentic sailing experience. Guests can relax on cushioned seating along the cabin top or enjoy the rear cockpit beside the captain while taking in the festive parade and afternoon sail.

⛵ Epiphany – Modern Catamaran

Experience the parade aboard Epiphany, our spacious Leopard 44 cruising catamaran designed for comfort and panoramic views.

With her wide beam and smooth ride, Epiphany provides a stable and relaxing platform for enjoying the parade and the sail afterward. Guests can spread out in shaded cockpit seating, relax on the bow, or lounge on the trampoline while taking in the celebration on the water.

What to Expect

• 250th Anniversary Celebration – Be part of a historic year as St. Michaels celebrates the United States Semiquincentennial with patriotic spirit on the water.

• Front-Row Parade Views – Be part of the parade itself as our boats join the decorated fleet along the St. Michaels waterfront.

• Scenic Chesapeake Bay Sailing – After the parade, relax on a beautiful sail out on the Miles River.

• Friendly & Experienced Crew – Our knowledgeable captains and crew ensure a safe, welcoming, and memorable sailing experience.

Location

Our sailing yachts depart from the Harbour Inn & Marina in the heart of St. Michaels, Maryland — a charming Eastern Shore town known for its maritime history, waterfront views, and excellent restaurants.

Conveniently located:
• 90 minutes from Philadelphia, Baltimore, and Washington, D.C.
• 1 hour from Annapolis

Arrive early to explore the town before your Flag Day cruise.

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:
Lady Patty has a small marine head for emergency use, and Epiphany features a private, spacious marine head. Both are located down a short set of steps. For all guests, we recommend using 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.

Children:
Children of all ages are welcome! Life jackets are available in infant, toddler, and youth sizes. Per U.S. Coast Guard regulations, all children count as passengers and require a ticket.

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:
Your cruise includes a complimentary glass of champagne to toast the evening. If bubbles aren’t your preference, wine, beer, or non-alcoholic beverages are happily provided instead. Additional beverages are available for purchase by the glass, and guests also have the option to add an open bar package during checkout.

We also 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?

Don’t miss this special Flag Day cruise during the United States’ 250th anniversary year.

With festive decorations, a patriotic atmosphere, and a relaxing sail on the Miles River, this special event is a unique way to enjoy the Chesapeake Bay.

Book your Flag Day Boat Parade Cruise today — spots are limited and this event fills quickly!