2 Hour Relaxing Chesapeake Day Sail

Enjoy 2-Hours of Sailing on the Chesapeake Bay

(Available on a per person basis or as a private charter)

Ready to embark on an unforgettable adventure? Enjoy a two-hour cruise with knowledgeable, first-class captains and a friendly crew dedicated to creating an unforgettable experience. Choose between our two stunning sailing yachts: the historic Lady Patty, a 1935 Maryland-built ketch, or Epiphany, a spacious and modern 44-foot Leopard catamaran.

Epiphany, our 44-foot Leopard catamaran, is the ideal setting for a relaxing day on the water with up to 6 of your family members and friends. Epiphany is also available for private bareboat charters to hold up to 13 guests. Designed for comfort, she features both forward and aft cockpit areas covered by a continuous hardtop, offering excellent protection from the elements. The aft cockpit’s spacious dining table is the perfect spot to enjoy a charcuterie board along with a selection of wine, beer, and soft drinks available for purchase. Up front, the trampoline area offers a relaxing place to sunbathe or simply soak in the sweeping Chesapeake Bay views as we sail. Epiphany is the perfect setting for a family reunion, anniversary celebration, or any special gathering on the water!

Out on the open water, our sailboats offer your choice of a public or private cruise in one of the most beautiful places to sail. Chesapeake Bay sailing is renowned for its stunning scenery and unforgettable sunsets. Your charter begins with a peaceful glide through the harbor before heading out into the Miles River, where you’ll enjoy sweeping views and, if you’re lucky, wildlife sightings like osprey and bald eagles. Several years, we have even spotted dolphins!

Our sailing yachts are docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland—a charming Eastern Shore town known for its incredible seafood and inviting small-town atmosphere. Whether you’re planning a day trip to St. Michaels or seeking a sailing charter on the Eastern Shore of the Chesapeake Bay, our relaxing sailboat excursions are conveniently located just 90 minutes from Philadelphia, Baltimore, and Washington, D.C., and only an hour from Annapolis.

You are welcome to participate as a working crew member or simply sit back and relax; we’re here to help you complete your historic yacht experience!

What to expect:

Immaculate Sailboats: Our beautifully kept sailing boats offer a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of our sailboats, making it the perfect setting for a memorable trip on the water.

Friendly and Experienced Crew: Our knowledgeable and engaging crew will enhance your sailing experience by providing valuable insights about the area and sailing. Guests have raved about the crew’s friendliness and expertise, making them feel welcome and comfortable throughout the trip.

Tranquil Sailing Trip: Take a break from the hustle and bustle of daily life with our peaceful and serene sailing experience. Guests have consistently praised the calming and rejuvenating experience of being on the water, creating the perfect escape from the stresses of everyday life.

Captivating Narratives: Our interesting stories and information about the area and sailing will provide an educational and engaging experience that enhances the trip. Guests have appreciated the captivating narratives shared by the crew, providing a deeper understanding of the area and sailing.

Historic Sailboat: Sailing on Lady Patty is a unique opportunity to help preserve a historical treasure. We appreciate your support! Guests have raved about the unforgettable experience of sailing with us, recommending it to friends and family as a must-do activity.

Amenities:

• Weather: We want to ensure your safety and comfort, hence the captain may decide to cancel due to bad weather, and this decision is made 15 minutes prior to departure. Rest assured there is no charge if the sail gets cancelled. We’re often asked whether we sail in rainy weather. We do sail even if it’s lightly misting, but not in heavy rain as we want you to have the best experience possible. It’s no fun sitting on the pouring rain! Epiphany has several covered options as well to get out of the elements if needed.
• Beverages: **Beer/wine tasting add-on is only an additional $20 per person (21 and older). The beer tasting is an unlimited sampling of 6 Maryland craft beers, the wine tasting is a flight of 3 whites & 3 reds plus a glass of your favorite wine. Or you can simply buy by the glass: Icy Cold Beer $7, Wine and Champagne $12. Coke, Diet Coke, Sprite are also available for sale, and bottled water is complimentary. BYOB $25.**

• Swag: Our ships store includes custom St. Michaels Sailing Charters embroidered shirts, baseball caps, zip hoodies, tote bags, beach towels, stemless wine glasses, and more.  You can pre-order at checkout or let our crew know you are interested in shopping for a souvenir.
• Comfortable Seating: Lady Patty offers seating along each side of the wooden cabin top as well as cushioned seating in the rear cockpit area with the captain. Epiphany has numerous cushioned seating options in covered front and rear cockpit areas with two dining tables. Guests can also lounge on comfy beanbag chairs or captains reclining chairs on the bow for a front row view of the sail. All seating offers great visibility of the journey.

• Attire: Be sure to bring comfortable shoes, cameras, sunhats, and a light jacket in spring and fall. It’s about 10 degrees cooler on the water so plan accordingly.
• Max 13 passengers: Children of all ages are welcome aboard our yachts. We love kids! We have infant, toddler, and youth life jackets to fit all sizes and ages. The U.S. Coast Guard considers all children (regardless of how small they are or what age they are) to be passengers, and as such, you need to count them in, too. For example, mom, dad, and their six-month-old are three guests, not two.
• Safety: Our yachts are exceptionally clean and well-maintained, with all modern safety features (life jackets, VHF etc). Foul weather gear is available in the event of unexpected bad weather.
• Cancellation 24/72 hrs: Reservations made on a per person basis can be cancelled up to 24 hrs before departure for a full refund.  72 cancellation for private charters.
• Toilet: Epiphany features a modern marine bathroom (head) located down a short set of steps. Lady Patty also has a more rustic head, accessed in the same way. We recommend using the lobby restroom at the Harbour Inn before boarding for added convenience.
• Accessibility: Getting aboard is easy most of the time unless we have an extremely high or extremely low tide in which case there is a step up or a step down to get aboard. Most of the time the deck is just about the same height as the dock so its a simple to walk aboard.  Once on deck there are 2 steps down into the cockpit.  Our Captain and first mate are there to assist any one who needs a hand while on the stairs.  So far we’ve been able to get everyone on and off regardless of capability, yea!
• Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663.  If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boats tie up.

Please note: If you are not booking a private charter, this sail requires two or more people. Amusement tax and crew gratuity added on.

Still have questions? ☎ 410-849-9864