We Found These Experiences For You (42)
St Michaels, MD
The Original St. Michaels Ghost Tour
SPIRITS OF ROWDY WOMEN | Starting at $20 | 1.75 hrs
Step back in time when you take this night time walk through this haunted harborside town. There are spirits of Rowdy Women (and a few men) lurking in the parks, the restaurants, the museums, and even in the graveyard. This is the Original St. Michaels Ghost Tour now in its 14th year with authentic stories ...
St Michaels
1.75 hours
Kid-Friendly
Ghost Tour, Walking Tour
Chesapeake Ghost Walks
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Solo Kayak Rental
St Michaels
2 Hours - 7 Days
Kayak
Shore Pedal & Paddle
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Tandem Kayak Rental
St Michaels
2 Hours - 7 Days
Kayak
Shore Pedal & Paddle
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Stand-Up Paddleboard Rental
St Michaels
2 Hours - 7 Days
SUP
Shore Pedal & Paddle
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History & Folklore
1 Hour • All Ages • Pet Friendly • Drinks and Snacks Welcomed
An hour long cruise narrated by your captain! Duration 1 hour About Narrated cruise with the Captain through the St. Michaels Harbor and Miles River Float through the St. Michaels Harbor, Miles River, and Long Haul Creek while exploring the history and folklore that fill the shoreline. Our history begins ...
St Michaels
St. Michaels Harbor Shuttle Services
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Sunset Cruise
75 Minutes • All Ages • Pet Friendly • Drinks and Snacks Welcomed
Our BYOB Sunset Cruise is a "must-do"! Duration 75 Minutes About Crank some tunes of your choice, sip on a beverage, and enjoy the sunset from the Miles River. Tours depart daily from our main port on Mulberry Street near the Crab & Steak Restaurant. More info Drinks and snacks are welcome ...
St Michaels
St. Michaels Harbor Shuttle Services
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Private Cruises
Up to 4 Hours • All Ages • Pet Friendly • Drinks and Snacks Welcomed
Private boat charters for up to 28 people. Rates 1 Hour Cruise: $400 2 Hour Cruise: $800 3 Hour Cruise: $1,200 4 Hour Cruise: $1,600 5 Hour Cruise: $2,000 Full Day Cruise: $3,000 Any cruise with a request to depart from a location outside of the 21663 zip code is subject to a one-time $350 travel fee. ...
St Michaels
Private Tours
St. Michaels Harbor Shuttle Services
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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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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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Large Group & Private Charter Catering on Lady Patty
Chef-Prepared Onboard Dining
Hambleton House offers chef-prepared meals and thoughtfully curated menus for guests seeking a more substantial onboard dining experience. From brunch favorites to full dinners, these menus pair beautifully with a relaxing day on the water. *Available for group of 6 or more. Orders must be placed 7 days ...
St Michaels
Private Tours
St. Michaels Sailing Charters
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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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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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Special 250th Anniversary Flag Day Celebration Cruise on Epiphany
$340 Per Passenger Or $1995 Private Charter | 3.5 Hours | Max 6 People
Step aboard the modern sailing catamaran Epiphany and experience St. Michaels’ Flag Day Boat Parade from the best seat on the water. Enjoy front-row views of a festive fleet of red, white, and blue–decorated boats as they cruise along the waterfront. Stretch out and relax on spacious decks, take ...
St Michaels
3.5 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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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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Large Group & Private Charter Catering on Epiphany
Chef-Prepared Onboard Dining
Hambleton House offers chef-prepared meals and thoughtfully curated menus for guests seeking a more substantial onboard dining experience. From brunch favorites to full dinners, these menus pair beautifully with a relaxing day on the water. *Available for group of 6 or more. Orders must be placed 7 days ...
St Michaels
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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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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Private Sailing Catamaran Charter on Epiphany - Up to 13 People
Private Bareboat Sailing Charter on Epiphany | Up to 13 People | All Ages Welcome!
Explore the St Michaels area of Chesapeake Bay. Join St. Michaels Sailing Charters on our 44-foot sailing catamaran Epiphany for a private 2 hour bareboat day sail that is bound to have everyone smiling ear to ear! Your hired captain will depart the dock and taking a brief harbor cruise, offering beautiful ...
St Michaels
2 or more hours
Private Tours
Sailing
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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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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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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St. Michaels Sailing Charters Merchandise
Ships Store: Elite St. Michaels Sailing Charters Merchandise!
St. Michaels Sailing Charters has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water. And easy to purchase while making your booking. We offer numerous options including clothing items ...
St Michaels
Sailing
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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Boxed Lunches on Lady Patty
Fresh Boxed Lunches for Your Sailing Experience
Perfect for daytime sails, corporate outings, and casual cruises, The Village Shoppe offers fresh boxed lunches designed for easy onboard dining while enjoying time on the water. Each boxed lunch includes a sandwich selection, chef’s choice side salad, potato chips, and dessert. *Orders must be placed ...
St Michaels
St. Michaels Sailing Charters
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