Chesapeake Bay Sunset Champagne Sail

Your Sailing Experience

Begin your evening with a relaxing harbor cruise through historic St. Michaels, including views of the 1879 Hooper Strait Lighthouse, before gliding out onto the scenic Miles River.

As the light begins to soften, enjoy peaceful Chesapeake Bay waters, fresh breezes, and the chance to spot local wildlife such as osprey and bald eagles. Enjoy a glass of complimentary champagne as the sky transforms into warm shades of gold, pink, and orange.

Your cruise concludes with a stunning view of the sun setting over the water — the perfect backdrop for date nights, anniversaries, celebrations, or simply a memorable evening on the Bay.

Whether you prefer a quiet, romantic escape or a relaxed gathering with friends, our friendly captains and attentive crew ensure your sunset sail is smooth, safe, and unforgettable.

Choose Your Vessel

⛵ Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

⛵ Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

What Guests Love

• Golden Hour Views: Unmatched Chesapeake Bay sunsets from the water

• Champagne Service: A celebratory touch that elevates the experience

• Romantic Atmosphere: Perfect for proposals, anniversaries, and special occasions

• Relaxing Escape: Peaceful evening breezes and calm waters

• Exceptional Crew: Friendly, knowledgeable captains who create a welcoming experience

Location

Our sailing yachts are docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland, a charming Eastern Shore town celebrated for its fresh seafood, historic streets, and welcoming small-town atmosphere.

Whether you’re planning a day trip to St. Michaels or a sailing charter on the Eastern Shore of the Chesapeake Bay, our excursions are conveniently located:

• 90 minutes from Philadelphia, Baltimore, and Washington, D.C.

• 1 hour from Annapolis

Arrive early to explore the quaint town, enjoy local restaurants, or stroll along the waterfront before your relaxing sail.

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 glass of champagne, but if bubbles aren’t your preference, wine, beer, and non-alcoholic beverages are happily provided instead. Additional beverages are available for purchase by the glass. We 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?

Experience the beauty of the Chesapeake Bay from the deck of a sailing yacht at sunset. Whether you’re planning a romantic outing, family adventure, or relaxing escape with friends, your time on the water awaits.

Book your 2‑Hour Sunset Champagne Sail now! Spots fill quickly, especially on weekends — reserve your seats today! 👉