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Half-Day Private Sail on Epiphany

Cruise through historic St. Michaels Harbor, then sail up the scenic Miles River on this unforgettable half-day adventure on a spacious catamaran Epiphany!

Quick Details

  • Duration: 4.5 Hours
  • Ages: All ages
  • Availability: Daily
  • Occupancy: 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)
  • Check-in: 15 minutes prior to departure
  • Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
  • Free Cancellation: 14 days before departure (50% refund up to 5 days before departure)
  • Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Private Charter

$ 1,695

Your Half Day Sailing Experience

Step aboard Epiphany, a spacious and stable modern catamaran built for comfort, socializing, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully arranged seating areas, Epiphany provides a relaxed yet luxurious sailing experience — perfect for families, couples, or small groups looking to enjoy a leisurely half-day on the water.

Guests can settle into abundant cushioned seating in shaded front and rear cockpit areas, complete with dining tables for drinks and snacks, or lounge at the bow in reclining captain’s chairs and comfy beanbags for a front-row view of the sails. Many guests also enjoy stretching out on the trampoline, feeling the breeze, and watching the water glide beneath them. Whether you prefer to sit back and relax or try your hand at sailing, Epiphany ensures a comfortable and engaging experience.

Depart from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse, before venturing onto the scenic Miles River. Take in sweeping Chesapeake Bay vistas, peaceful waters, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you’re seeking a relaxing scenic escape or a fun, interactive outing, our friendly captains and attentive crew make your half-day sail aboard Epiphany safe, memorable, and truly enjoyable.

Couple sitting on a boat in sunset, holding glasses, with colorful sails in the background.

What Guests Love

  • Modern, Comfortable Layout: Ample cushioned seating and spacious areas allow you to relax and take in the scenic Chesapeake Bay views.

  • Friendly & Knowledgeable Crew: Captains share stories, local history, and sailing insight.

  • Relaxing Escape: Ideal for families, couples, or groups looking for a peaceful half-day on the water.

  • Beverages & Tasting Options: Beer and wine tastings are available for an additional fee; bottled water is complimentary. Soft drinks and champagne are also available for purchase.

Luxury yacht deck with dining table, seating area, and view of water and shoreline.

Location

Epiphany is 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.

Sunset behind a lighthouse by the water with boats and trees silhouetted.

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:
Epiphany has a private, roomy marine head just a few steps down. We suggest all guests use 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.

Catamaran sailing with red and blue spinnaker on a clear day at sea.

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:
Beer and wine tastings are available for an additional fee, along with optional sodas and champagne for purchase. Bottled water is complimentary. 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 modern sailing catamaran. Whether you’re planning a romantic outing, family adventure, or relaxing escape with friends, your time on the water awaits.

Book your Half Day Private Sail now! Spots fill quickly, especially on weekends — reserve your seats today! 👉

Three people relaxing on bean bags on a boat's deck over water.

Still Have Questions?

We’re happy to help you plan the perfect experience.

☎ 410-849-9864
✉ [email protected]

We look forward to welcoming you aboard!

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