We Found These Experiences For You (33)
Two Hour Chesapeake Day Sail on Lady Patty
$95 Per Passenger Or $995 Private Charter | Max 13 People | Add On Beer/Wine Tasting!
Enjoy a relaxed two-hour sail aboard the historic 1935 Maryland-built ketch Lady Patty, guided by experienced captains and a friendly crew. Begin with a peaceful glide through the harbor before cruising the scenic Miles River and Chesapeake Bay, where sweeping shoreline views, osprey, bald eagles and ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Wine Tasting Cruise on Lady Patty
$115 Per Passenger Or $1195 Private Charter | Ages 21+ Only | Max 13 People | 2 Hours
Enjoy a relaxing two-hour wine tasting cruise on the Chesapeake Bay with St. Michaels Sailing Charters on our historic 1935 ketch sailboat Lady Patty. Sip six carefully curated wines—three reds and three whites—while gliding past scenic waterfront views and enjoying a mini-harbor tour. Whether you ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Beer Tasting Cruise on Lady Patty
$115 Per Passenger Or $1195 Private Charter | Ages 21+ Only | Max 13 People | 2 Hours
Enjoy a leisurely 2-hour beer tasting cruise aboard a historic 1935 ketch sailboat Lady Patty that pairs panoramic waterfront views with a rotating selection of craft beers. This relaxed, sensory-focused experience offers unlimited samplings of six thoughtfully chosen beers while you glide through the ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Sunset Champagne Cruise on Lady Patty
$115 Per Passenger Or $1195 Private Charter | Max 6 People | 2 Hours | Champagne
Experience a two-hour sunset champagne cruise aboard the historic 1935 ketch Lady Patty, drifting on the tranquil waters of Chesapeake Bay near St. Michaels. As the sun sets, enjoy the sea breeze, golden light, and the gentle sound of waves while sipping champagne and sampling light hors d’oeuvres. ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Bachelorette Bachelor Party Cruise on Lady Patty
Starting at $995 | Max 13 People | 2 Hours | Complimentary Champagne
Looking for a unique and unforgettable way to celebrate a bachelorette or bachelor party in St. Michaels, Maryland? Set sail aboard our historic 1935 ketch sailboat Lady Patty for a one-of-a-kind celebration on the water. Whether you’re toasting the bride or groom, soaking in Chesapeake Bay views, ...
St Michaels
2 hours
St. Michaels Sailing Charters
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Marriage Proposal Engagement Cruise on Lady Patty
Starting at $995 | Max 13 People | 2 Hours | Complimentary Champagne
Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a historic 1935 ketch sailboat Lady Patty. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water. Experience the perfect blend of luxury and personalized ...
St Michaels
2 hours
St. Michaels Sailing Charters
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Nautical Weddings & Elopements on Lady Patty
Boat Wedding Packages Start at $1445 | Max 13 People | Complimentary Champagne
Celebrate your love with a wedding or elopement on the water. St. Michaels Sailing Charters offers private sailboat ceremonies aboard our historic 1935 ketch sailboat Lady Patty, departing from the charming waterfront of St. Michaels, MD. With sweeping Chesapeake Bay views, our intimate sailboat weddings ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Half Day Private Sail on Lady Patty
Starting at $1895 | Max 13 People | 4.5 Hours
Explore the St Michaels area of Chesapeake Bay. Join St. Michaels Sailing Charters on our 1935 ketch sailboat Lady Patty for a private 4 1/2 hour day sail that is bound to have everyone smiling ear to ear! We begin by departing the dock and taking a brief harbor cruise, offering beautiful waterfront ...
St Michaels
4.5 hours
Private Tours
St. Michaels Sailing Charters
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Full Day Private Sail on Lady Patty
$2795 Private Charter | Max 13 People | 7 Hours
Explore the St Michaels area of Chesapeake Bay. Join St. Michaels Sailing Charters on our 1935 ketch sailboat Lady Patty for a private 7 hour full day sail that is bound to have everyone smiling ear to ear! We begin by departing the dock and taking a brief harbor cruise, offering beautiful waterfront ...
St Michaels
7 hours
Private Tours
St. Michaels Sailing Charters
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Private Sailing Lesson on Lady Patty
$995 Private Lesson | Max 13 People | 2 Hours | Learn To Sail A Historic Ketch!
Join a two-hour private sailing lesson aboard a historic 1935 ketch sailboat Lady Patty to learn hands-on sail handling and basic boat skills. Whether you are new to sailing or have prior experience, the lesson covers line handling, raising sails, steering, reading the wind, basic knots, the four points ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Special 4th of July Fireworks Cruise on Lady Patty
$175 Per Passenger Or $2095 Private Charter | 2 Hours | Max 13 People
Celebrate Independence Day aboard Lady Patty, our beautifully restored 1935 sailing ketch, for an unforgettable evening on the water in historic St. Michaels, Maryland. Enjoy a relaxing harbor cruise and sunset sail before settling in for one of the best views of the town’s spectacular 4th of July ...
St Michaels
2 Hours
Private Tours
St. Michaels Sailing Charters
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Two Hour Chesapeake Day Sail on Epiphany
$175 Per Passenger Or $895 Private Charter | Max 6 People | Add On Beer/Wine Tasting!
Set sail on the 2016 44-foot Leopard catamaran Epiphany for a relaxed two-hour cruise led by knowledgeable captains and a friendly crew. Glide through the harbor into the scenic Miles River while taking in sweeping water views, shoreline scenery, and possible wildlife sightings such as osprey, bald eagles ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Wine Tasting Cruise on Epiphany
$195 Per Passenger Or $995 Private Charter | Ages 21+ Only | Max 6 People | 2 Hours
Enjoy a memorable 2-hour wine tasting cruise on a modern 2016 44-foot catamaran in St. Michaels, MD. Sip six thoughtfully curated wines—three reds and three whites—while cruising the Chesapeake Bay and taking in picturesque waterfront views. The experience blends relaxed sailing, attentive crew service, ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Beer Tasting Cruise on Epiphany
$195 Per Passenger Or $995 Private Charter | Ages 21+ Only | Max 6 People | 2 Hours
Enjoy a relaxed, sensory-focused beer tasting aboard a modern 44-foot catamaran Epiphany with panoramic waterfront views. This intimate cruise features unlimited samplings of six rotating craft beers, curated to highlight creativity and flavor, while you glide through the harbor. With cozy seating and ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Sunset Champagne Cruise on Epiphany
$195 Per Passenger Or $995 Private Charter | Max 6 People | 2 Hours | Champagne
Experience a relaxed sunset cruise aboard a modern 44-foot sailing yacht Epiphany, sipping champagne as the sun sets over Saint Michaels and the Chesapeake Bay. This sensory cruise highlights golden light, gentle breezes and the soothing rhythm of the water while guests enjoy complimentary beverages ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Bachelorette Bachelor Party Cruise on Epiphany
Starting at $895 | Max 6 People | 2 Hours | Complimentary Champagne
Looking for a unique and unforgettable way to celebrate a bachelorette or bachelor party in St. Michaels, Maryland? Set sail aboard our spacious, modern 44-foot catamaran Epiphany for a one-of-a-kind celebration on the water. Whether you’re toasting the bride or groom, soaking in Chesapeake Bay views, ...
St Michaels
2 hours
St. Michaels Sailing Charters
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Marriage Proposal Engagement Cruise on Epiphany
Starting at $895 | Max 6 People | 2 Hours | Complimentary Champagne
Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a modern 44-foot catamaran Epiphany. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water. Experience the perfect blend of luxury and personalized ...
St Michaels
2 hours
St. Michaels Sailing Charters
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Nautical Weddings & Elopements on Epiphany
Boat Wedding Packages Start at $1345 | Max 6 People | Complimentary Champagne
Celebrate your love with a wedding or elopement on the water. St. Michaels Sailing Charters offers private sailboat ceremonies aboard our spacious, modern 44-foot catamaran Epiphany, departing from the charming waterfront of St. Michaels, MD. With sweeping Chesapeake Bay views, our intimate sailboat ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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Half Day Private Sail on Epiphany
Starting at $1695 | Max 6 People | 4.5 Hours
Explore the St Michaels area of Chesapeake Bay. Join St. Michaels Sailing Charters on our 44-foot sailing catamaran Epiphany for a private 4 1/2 hour day sail that is bound to have everyone smiling ear to ear! We begin by departing the dock and taking a brief harbor cruise, offering beautiful waterfront ...
St Michaels
4.5 hours
Private Tours
St. Michaels Sailing Charters
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Full Day Private Sail on Epiphany
$2495 Private Charter | Max 6 People | 7 Hours
Explore the St Michaels area of Chesapeake Bay. Join St. Michaels Sailing Charters on our 44 foot catamaran Epiphany for a private 7 hour full day sail that is bound to have everyone smiling ear to ear! We begin by departing the dock and taking a brief harbor cruise, offering beautiful waterfront views ...
St Michaels
7 hours
Private Tours
St. Michaels Sailing Charters
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Private Sailing Lesson on Epiphany
$895 Private Lesson | Max 6 People | 2 Hours | Learn To Sail A Modern Catamaran!
Learn to sail aboard our modern 44-foot Leopard catamaran in a focused two-hour private lesson designed for beginners and experienced sailors. Instructors cover line handling, raising the sails, steering, reading wind, basic knots, points of sail, sail trim and practiced tacking. The experience blends ...
St Michaels
2 hours
Private Tours
St. Michaels Sailing Charters
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ASA 104 Bareboat Cruising Course + IPC on Epiphany
Starting at $2395 Per Person | Max 4 Students & 2 Guests
ASA 104 Bareboat Cruising teaches sailors how to safely skipper and crew a cruising sailboat on multi-day coastal voyages. During this course aboard our Leopard 44 cruising catamaran Epiphany, students learn the practical skills required to plan and manage a cruise, operate onboard systems, and confidently ...
St Michaels
3 days
St. Michaels Sailing Charters
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ASA 114 Cruising Catamaran Course + IPC on Epiphany
Starting at $1595 Per Person | Max 4 Students & 2 Guests
The ASA 114 Cruising Catamaran certification introduces sailors to the unique handling and systems of modern cruising catamarans. This course takes place aboard Epiphany, allowing students to gain direct experience sailing and maneuvering a modern cruising catamaran in real-world conditions. Perfect ...
St Michaels
2 days
St. Michaels Sailing Charters
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Combo ASA 104 Bareboat Cruising Course and ASA 114 Catamaran Cruising Course + IPC on Epiphany
Starting at $3195 Per Person | Max 4 Students & 2 Guests
Take your sailing skills to the next level with our ASA 104 Bareboat Cruising and ASA 114 Cruising Catamaran combination course aboard Epiphany. This accelerated training package allows students to complete both certifications during one immersive sailing experience on our 44-foot catamaran, saving time ...
St Michaels
4 days
St. Michaels Sailing Charters
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Special 4th of July Fireworks Cruise on Epiphany
$265 Per Passenger Or $1575 Private Charter | 2 Hours | Max 6 People
Celebrate Independence Day aboard Epiphany, our spacious Leopard 44 cruising catamaran, for an unforgettable evening on the water in historic St. Michaels, Maryland. Enjoy a relaxing harbor cruise and sunset sail before settling in for one of the best views of the town’s spectacular 4th of July fireworks. ...
St Michaels
2 Hours
Private Tours
St. Michaels Sailing Charters
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Viewing 1 to 25 of 33 Experiences