Epiphany

Sailing on the Chesapeake Bay is one of the most memorable experiences visitors can have in St. Michaels. With gentle breezes, wide open water, and beautiful shoreline views, the bay offers perfect conditions for sailing.

Aboard Epiphany, guests can enjoy the peaceful rhythm of wind-powered travel while taking in the natural beauty of the Eastern Shore. From osprey nests and working waterfronts to historic waterfront homes and quiet coves, every sail offers something new to see.

Departing from the harbor in historic St. Michaels, Epiphany sails the Miles River, a tributary of the Chesapeake Bay, offering incredible views and a relaxing atmosphere away from the crowds.

Why Sail on Epiphany

Comfortable and Spacious
Epiphany provides plenty of room for guests to relax, enjoy the breeze, and take in the views while sailing.

Smooth and Relaxing Sailing
Designed for stability and performance, Epiphany delivers a smooth sailing experience that is enjoyable for both experienced sailors and first-time guests.

Perfect for Small Groups
Epiphany is ideal for families, couples, and small groups looking for a private and memorable sailing experience.

Scenic Chesapeake Views
Sail past waterfront towns, historic homes, wildlife habitats, and open bay views that make the Chesapeake Bay one of the most beautiful sailing destinations in the country.

Epiphany Specifications

• Type: Sailing Catamaran

• Home Port: St. Michaels, Maryland

• Waters Sailed: Miles River, a tributary of the Chesapeake Bay

• Passenger Capacity: Up to 13 Guests

• Experience Level: No sailing experience required

Guests are welcome to relax and enjoy the sail, or learn more about how the boat works and the basics of sailing.

Sailing Charters Aboard Epiphany

Epiphany offers a variety of sailing experiences designed to showcase the beauty of the Chesapeake Bay.

• Daytime Sailing Cruises – Enjoy a relaxing cruise on the Miles River while taking in the scenery, wildlife, and classic waterfront views of St. Michaels.

• Sunset Sailing – One of the most popular experiences on the Chesapeake Bay. Watch the sun sink below the horizon as the sky fills with color and the water glows with evening light.

• Private Charters – Perfect for birthdays, family gatherings, celebrations, or simply a special day on the water with friends.

• Custom Sailing Experiences – The crew can tailor a sailing experience to match your group, whether you want a peaceful sightseeing cruise or a more interactive sailing adventure.

What to Expect on Your Sail

A typical sailing charter aboard Epiphany is relaxed, scenic, and memorable.

As the sails fill with wind, the boat glides quietly across the water, creating a peaceful escape from the busy waterfront. Guests can enjoy the fresh Chesapeake Bay breeze, watch local wildlife, and take in some of the most beautiful views on Maryland’s Eastern Shore.

Bring a camera — the light, water, and scenery make every sail unique.

Frequently Asked Questions

Do I need sailing experience?
No experience is required. Guests are welcome to simply sit back and enjoy the ride.

Can we bring food or drinks?
Yes. Many guests bring snacks, wine, or a picnic to enjoy while sailing.

Is Epiphany good for families?
Yes. Sailing is a fun and relaxing activity for guests of all ages.

What if the weather is bad?
Safety always comes first. If weather conditions are unsafe, charters can be rescheduled.

Book Your Sailing Adventure

Experience the beauty of the Chesapeake Bay aboard Epiphany.

Join us for a relaxing sail from St. Michaels, Maryland, and discover why sailing is one of the best ways to experience the Eastern Shore.

Book your sailing adventure today and enjoy the Chesapeake Bay from the deck of Epiphany.