Discover a relaxing way to explore Maryland’s Eastern Shore with a Chesapeake Bay wine tasting cruise in St. Michaels. This two-hour sailing experience invites guests aboard a classic sailboat to enjoy gentle bay breezes, scenic waterfront views, and a guided wine tasting led by the experienced crew.

During the sail, guests sample six thoughtfully selected wines, including three reds and three whites, chosen to highlight a variety of flavors and styles. The curated wine list changes regularly, creating a fresh and unique tasting experience on each cruise. As the sails catch the wind, the boat glides past the historic harbor and out onto the Miles River, offering sweeping views of the Chesapeake Bay.

With intimate group sizes, friendly service, and beautiful coastal scenery, this St. Michaels wine tasting cruise delivers a memorable combination of sailing, wine education, and waterfront relaxation in one of Maryland’s most charming maritime towns.

Any restrictions to participate?

• Age: 21+

Who can you accommodate for?

• Children: This is not an experience for children.
• 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:
  • 2 hour cruise
  • Tastings of three red and three white wines
  • There are additional beverages (beer, wine, and sodas) for purchase on the ship. You are also 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.
  • 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.
• 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.
• Restrooms/ lockers/ changing rooms: 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.