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2-hour scenic sail on the Chesapeake Bay aboard the modern Epiphany catamaran
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Option to help raise sails or relax on deck while enjoying the bay breeze
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Stunning views of the Miles River, harbor, and possible wildlife sightings
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Comfortable seating with expert crew providing a relaxing, memorable experience
2 Hour Relaxing Chesapeake Day Sail on Epiphany
About Tour
Enjoy a peaceful 2‑hour sailing adventure aboard the spacious and modern Epiphany catamaran on the scenic Chesapeake Bay from St. Michaels, Maryland. Whether you choose to help hoist the sails or simply relax on deck, this tranquil cruise glides through the harbor and out onto the Miles River with sweeping water views and possible wildlife sightings like ospreys and eagles. With comfortable seating, friendly and knowledgeable crew, and the gentle rhythm of the bay breeze, this day sail offers a rejuvenating way to experience Chesapeake Bay’s beauty and charm.
- Duration: 2 hours
- Group Size: 6
- Ages: All ages
- Live Guide: English
Why travelers love this
(3 reviews)
5.0 out of 5 stars (based on 3 reviews)
(3 reviews)
4.9
Suitable for beginners
Professional local guide
Safety-First Experience
Highlights
What does the 2-Hour Relaxing Chesapeake Day Sail include?
This cruise is a 2-hour scenic sailing adventure aboard the Epiphany catamaran, offering beautiful views of the Chesapeake Bay, St. Michaels Harbor, and surrounding waterways. Guests can relax, enjoy the breeze, and observe the local scenery. Complimentary bottled water is provided, and additional beverages like beer, wine, and soda are available for purchase on board. The experienced crew may also share insights about local history and sailing.
What should I know about booking, weather, and what to bring?
It’s recommended to arrive 15 minutes before departure. You can cancel a per-person booking up to 24 hours before the sail for a full refund; private charters have different cancellation policies. Sailing can continue in light mist but may be canceled for safety in severe weather, with a full refund issued. Guests should bring sunscreen, sunglasses, a hat, and a light jacket since it can be cooler on the water.
Laura & GM Bell
CEO / Founder
About the operator
St. Michaels Sailing Charters offers exceptional sailing experiences from the scenic waters of St. Michaels, Maryland, providing guests with a memorable blend of relaxation, adventure, and local maritime charm. Whether you’re seeking a romantic sunset cruise, a private charter for family and friends, or a customized sailing excursion on the Chesapeake Bay, their experienced crew delivers top-notch service and personalized attention from start to finish.
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Enjoy a relaxing wine tasting cruise aboard the Epiphany catamaran on Chesapeake Bay. Sip curated wines, admire scenic harbor views, and unwind with friendly crew on tranquil waters.
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Customer Photos
Reviews
5.0 out of 5 stars (based on 3 reviews)
Perfect Way to See Chesapeake Bay
February 24, 2026
Absolutely loved this day sail! The experience was peaceful and scenic, with gorgeous water views and a relaxed pace. The crew was professional and welcoming, making this experience truly enjoyable from start to finish. Will definitely sail again!
Great Family Experience
February 24, 2026
This relaxing sail was the highlight of our family trip! The boat was spacious and comfortable, and everyone from kids to adults had a great time. The crew shared some interesting stories about the Bay and made sure we were all comfortable throughout. A must-do activity!
A Tranquil and Beautiful Bay Sail
February 24, 2026
We thoroughly enjoyed the 2-hour sail aboard Epiphany. The views of the Chesapeake Bay were stunning, and the crew was friendly and attentive. It was the perfect way to unwind and take in the beauty of St. Michaels from the water. Highly recommend for anyone visiting the area!
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