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Sailing Schedule:
April 18-Sept 7: 10-12, 12:30-2:30, 3-5, 5:30-7:30, 7:30-9:30
Sept 8 -Sept 30: 10-12, 12:30-2:30, 3-5, 5:30-7:30
Oct 1- Nov 2: 9-11, 11:30-1:30, 2-4, 4:30-6:30
We sail 7 days a week all season long.
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Lady Patty is Coast Guard licensed to carry a maximum of 13 guests. This limit is set by law and applies to everyone on board, regardless of age or size—so, for example, 13 adults and 1 infant would exceed the allowed capacity.
Epiphany is licensed to carry a maximum of 6 guests for standard charters. However, for private bareboat charters, she can accommodate up to 13 guests.
If you have a group of 14 or more, please call 410-849-9864 to explore additional options. We also book for another sailboat here in St. Michaels that can accommodate up to 24 passengers, and we’d be happy to arrange that reservation for you!
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You can email us at [email protected]. We should respond within 24 hours. To rebook to another date/time either email or call 410-849-9864.
Our Cancellation Policy is:
- 72 hours on Private Charters & Sunset Sails
- 72 hours on wine tasting cruises, beer tasting cruises & private sailing lessons
- 24 hours on per person Day Sails
Customers will receive a full refund or credit* with proper cancellation notice. Customers will also receive a full refund or credit* in case of operator cancellation due to weather or operator cancellation due to other unforeseen circumstances. No-shows will be charged the full price.
*Does not include online booking fees
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You are welcome to cancel your reservation and get a full refund* up to 72 hours before departure on private charters, beer & wine tasting cruises, sailing lessons, and sunset champagne cruises.
You are welcome to cancel your reservation and get a full refund* up to 24 hours before departure on our 2 hour Chesapeake Day Sails.
*Does not include online booking fees
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We understand that unforeseen circumstances, such as traffic or family emergencies, can arise. Unfortunately, missed trips are non-refundable. We recommend planning your journey to arrive well in advance to account for potential delays.
If you anticipate challenges in making it to your scheduled trip, please contact us as soon as possible. While we cannot guarantee a refund, we may be able to fill your seats from our wait list. The sooner you let us know, the more likely that is to happen. Your understanding and cooperation are greatly appreciated.
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Yes! We sail on every trip—except in rare cases when conditions make it unsafe, such as extremely high winds or when there’s no wind at all. In those situations, we may keep the sails down and continue your tour under power. Otherwise, we’re sailing.
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Sail Selina monitors weather conditions closely. In the event of bad weather (storms, high winds, etc.) the captain on watch makes the decision to cancel 15 minutes before departure.
In the event of a cancelled trip we will make every effort to reschedule or refund your trip. If it is obvious well before departure time, the captain may cancel sooner in which case you would receive a text message from them directly.
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Absolutely! St. Michaels Sailing Charters offers private charters for all your special occasions. Private charters are available on all of our cruises. You can book these online with the ‘book now’ button or call 410-849-9864 for more information.
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Absolutely! We offer convenient free parking where we are docked 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 police boats and work boats tie up.
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Unfortunately our yachts are not wheelchair accessible. With that said, we are able to get most folks aboard, and assist even those with limited mobility. If your guest can walk a step or two and go down and up 2 stairs we can help get them aboard. Good news is that we have gotten just about everyone aboard that has wanted to go for a sail. If your guest is completely wheelchair bound then we recommend you call us at 410-849-9864 to discuss your personal needs.
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Yes, children of all ages are welcome on all our family-friendly trips, (although the wine & beer tasting and champagne cruises lend themselves to an adult audience). 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 purchase a ticket for each child. For example, mom, dad, and their six-month-old are three guests, not two.
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Yes we have life jackets for kids of all sizes, from infants to toddlers to tweens & teens.
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- Yes we are fido friendly if the weather is 80’ or cooler. Over 80′ pooch is very uncomfortable and we know you love your pet and wouldnt want him to suffer in the heat for two hours.
- We do ask that pooch has his claws covered so booties for big guys and a basket or carrying bag for the little ones.
- Please note that a $25 cleaning fee applies for pets aboard Sail Selina II to ensure a comfortable experience for all guests. Thank you for your understanding! Charged the day of your sail.
- As you may know, Selina II has lots of varnished surfaces, easily scratched by tiny claws, so we simply ask that pets be in a carrier — like a bag or basket — or wearing booties. That way, when something exciting happens (a bird flies over, a bee buzzes about, a big wave rocks the boat) and your pup scrambles, the scrambling doesn’t end up damaging the boat.
Captain Iris hates this, but since guests have broken the rules and their dogs have damaged the boat, we have a $100 fee if Fido gets loose. Since that policy got put in place, all our guests are very attentive to their pets’ paws. We recommend that you have Fido in their booties 5 minutes before departure to be ready to board at that time. If it is the first time they have used booties you may want to practice ahead to know how long it will take you to get their booties securely on their paws. We hope we get to have you and your people-friendly pet aboard! -
On outings where it is not included, sodas, beer, wine, and champagne are available for sale. Bottled water is supplied and is complimentary.
Our BYOB cork fee is $25 and covers everyone in your group.
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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.
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Lady Patty is Coast Guard licensed to carry a maximum of 13 guests. This limit is set by law and applies to everyone on board, regardless of age or size—so, for example, 13 adults and 1 infant would exceed the allowed capacity.
Epiphany is licensed to carry a maximum of 6 guests for standard charters. However, for private bareboat charters, she can accommodate up to 13 guests.
If you have a group of 14 or more, please call 410-849-9864 to explore additional options. We also book for another sailboat here in St. Michaels that can accommodate up to 24 passengers, and we’d be happy to arrange that reservation for you!
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- We partner with Royal Oak Catering Company and Aboard Charcuterie to offer custom, pre-ordered food options that can be ready when you arrive. You can view these selections during the reservation process, or call us at 410-849-9864 for more details.
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Our sailing catamaran, Epiphany, offers multiple shaded spots, including the forward and aft cockpit areas, each with dining tables and plenty of seating. Our historic 1935 ketch, Lady Patty, does not have built-in shade except for what the sails provide depending on wind direction. If you need a break from the sun, you’re welcome to step below deck into the cabin. We always recommend bringing sunscreen and sun hats!
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Click our “Book Now” button on the website, select your preferred date and trip, and follow the easy booking process. Or you can call us at 410-849-9864.
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We offers a variety of captivating sailing experiences, including:
- tranquil day trips
- delightful wine & beer tasting cruises
- immersive sailing lessons
- serene champagne sunset sails
- private charters
Let the wind guide you as you take in the sights, sounds, and sensations of the Chesapeake Bay, tailored to your perfect escape.
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We answer our emails within 24 hours. [email protected]
We answer our phone 8:00am – 7:30pm seven days/week. 410-849-9864
It rarely happens but if we dont answer, keep trying!
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We recommend bringing sunscreen, a hat, comfortable clothing, and any personal items you may need. Bottled water is available aboard and is complimentary.
