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Duration: 2 hours

Overview

Enjoy a peaceful 2-hour Chesapeake Bay sailing tour in St. Michaels, Maryland aboard the classic sailboat Lady Patty. Take in sweeping waterfront views, fresh bay breezes, and the laid-back charm of Maryland’s Eastern Shore during this relaxing sailing experience.

🌊 Enjoy a 2-hour Chesapeake Bay sailing cruise in St. Michaels, Maryland aboard the Lady Patty

⛵ Relax as the captain guides the sailboat along the Miles River and surrounding bay waters

🌅 Take in scenic views of the Eastern Shore coastline and St. Michaels harbor

👨‍✈️ Learn about local sailing traditions and the maritime history of the Chesapeake Bay

Experience the beauty of Maryland’s Eastern Shore on a 2-hour relaxing Chesapeake Bay day sail aboard the Lady Patty in St. Michaels, Maryland. This scenic sailing cruise offers a peaceful way to explore the Miles River and surrounding Chesapeake Bay waters while enjoying the gentle rhythm of the wind and waves.

As the sailboat glides across the bay, guests can sit back and take in panoramic views of the shoreline, historic harbor, and coastal landscapes that make St. Michaels one of the region’s most beloved waterfront towns. The knowledgeable captain shares insights about local sailing traditions and the maritime heritage that has shaped the Chesapeake Bay for generations.

This St. Michaels sailing experience is designed for comfort and relaxation, allowing guests to unwind, enjoy the fresh air, and fully appreciate the natural beauty of the bay during an unforgettable two-hour sail.

Experience the beauty of Maryland’s Eastern Shore on a 2-hour relaxing Chesapeake Bay day sail aboard the Lady Patty in St. Michaels, Maryland. This scenic sailing cruise offers a peaceful way to explore the Miles River and surrounding Chesapeake Bay waters while enjoying the gentle rhythm of the wind and waves.

As the sailboat glides across the bay, guests can sit back and take in panoramic views of the shoreline, historic harbor, and coastal landscapes that make St. Michaels one of the region’s most beloved waterfront towns. The knowledgeable captain shares insights about local sailing traditions and the maritime heritage that has shaped the Chesapeake Bay for generations.

This St. Michaels sailing experience is designed for comfort and relaxation, allowing guests to unwind, enjoy the fresh air, and fully appreciate the natural beauty of the bay during an unforgettable two-hour sail.

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Year-Round,
Daily (excluding holidays)

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Year-Round,
Daily (excluding holidays)

Any restrictions to participate?

  • Age: All ages are welcomed.

Who can you accommodate for?

  • Children: All participants must have a paid ticket to participate, children included.
    • Life jackets are available in infant, toddler, and youth sizes. Per U.S. Coast Guard regulations, all children count as passengers and require a ticket.
  • Individuals with disabilities: The yachts are not wheelchair accessible.
    • With that said, the provider is 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 they can help get them aboard. 
    • If your guest is completely wheelchair bound then we recommend you call the provider to discuss your personal needs.
  • Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

  • Duration: 2 Hours
  • What’s included:
    • Sightseeing cruise
    • Bottled water
    • There are beverages (beer, wine, and sodas) for purchase on the ship. You are welcome to bring your own beverages for an additional fee.
  • Who will be present: Your captain, crew and other guests (up to 13 people)
  • Spectators: No spectators are allowed, everyone must have a ticket
  • Photo/ video: Photos are allowed and encouraged.

How to prepare?

  • Weather dependency: It is at the captain’s discretion to cancel due to weather. This decision is made 15 minutes prior to departure.
  • Arrival: 15 minutes prior to departure
  • Parking: Guests may park in the hotel lot or along the waterfront on Harbor Road past the police boats.
  • What to wear: Wear comfortable shoes or something easy to remove if you prefer to go barefoot. Ladies, please avoid high heels. Light jackets or layers are recommended on cooler days.
  • What to bring: Your reservation confirmation, phone, and extra money for on-board purchases
    • Guests are welcome to bring light snacks or handheld items at no additional charge. Due to the intimate layout of Lady Patty and the nature of shared group bookings, plates, napkins, silverware, and serving ware are not provided and cannot be accommodated onboard.
    • If using spray sunscreen, please apply before boarding to protect the varnish. Don’t worry if you forget your sunhat — custom baseball caps are available for purchase onboard.
  • Restrooms/ lockers: Lady Patty has a small marine head for emergency use, located down a short set of steps. Guests are encouraged to use the Harbour Inn lobby restrooms before boarding.

Any restrictions to participate?

  • Age: All ages are welcomed.

Who can you accommodate for?

  • Children: All participants must have a paid ticket to participate, children included.
    • Life jackets are available in infant, toddler, and youth sizes. Per U.S. Coast Guard regulations, all children count as passengers and require a ticket.
  • Individuals with disabilities: The yachts are not wheelchair accessible.
    • With that said, the provider is 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 they can help get them aboard. 
    • If your guest is completely wheelchair bound then we recommend you call the provider to discuss your personal needs.
  • Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

  • Duration: 2 Hours
  • What’s included:
    • Sightseeing cruise
    • Bottled water
    • There are beverages (beer, wine, and sodas) for purchase on the ship. You are welcome to bring your own beverages for an additional fee.
  • Who will be present: Your captain, crew and other guests (up to 13 people)
  • Spectators: No spectators are allowed, everyone must have a ticket
  • Photo/ video: Photos are allowed and encouraged.

How to prepare?

  • Weather dependency: It is at the captain’s discretion to cancel due to weather. This decision is made 15 minutes prior to departure.
  • Arrival: 15 minutes prior to departure
  • Parking: Guests may park in the hotel lot or along the waterfront on Harbor Road past the police boats.
  • What to wear: Wear comfortable shoes or something easy to remove if you prefer to go barefoot. Ladies, please avoid high heels. Light jackets or layers are recommended on cooler days.
  • What to bring: Your reservation confirmation, phone, and extra money for on-board purchases
    • Guests are welcome to bring light snacks or handheld items at no additional charge. Due to the intimate layout of Lady Patty and the nature of shared group bookings, plates, napkins, silverware, and serving ware are not provided and cannot be accommodated onboard.
    • If using spray sunscreen, please apply before boarding to protect the varnish. Don’t worry if you forget your sunhat — custom baseball caps are available for purchase onboard.
  • Restrooms/ lockers: Lady Patty has a small marine head for emergency use, located down a short set of steps. Guests are encouraged to use the Harbour Inn lobby restrooms before boarding.

Unused Experience Vouchers can be returned within 14 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 72 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 72 hours in advance means losing the value of your experience.

Unused Experience Vouchers can be returned within 14 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 72 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 72 hours in advance means losing the value of your experience.

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