2-Hour Chesapeake Bay Sail from St. Michaels: Historic Lady Patty

Two hours on the water: the Hooper Strait Lighthouse, wildlife sightings, and the crew's stories of the bay

A two-hour sail aboard the historic Lady Patty departing from Harbour Inn in St. Michaels, Maryland, where you glide through Chesapeake Bay waters and past the Hooper Strait Lighthouse, one of only four remaining screw-pile lighthouses on the bay. The boat holds a maximum of 13 guests, ensuring a personalized experience. A live English-speaking guide shares stories about the area and sailing while you watch for osprey and dolphins. Life jackets, water, rain jackets, binoculars and parking are included, along with 20% gratuity for the captain and crew.

Step-by-step itinerary

Relaxing 2-hour Chesapeake Bay sail

• Depart from Harbour Inn, St. Michaels
• Sail through St. Michaels harbor
• View Hooper Strait Lighthouse up close
• Spot wildlife like osprey and dolphins
• Enjoy beer and wine tasting (adults)
• Listen to crew stories about sailing
• Return to Harbour Inn

The experience

The Lady Patty leaves from Harbour Inn at 101 N Harbor Road in St. Michaels, a departure point that sits right on the water. Two hours aboard means you spend the bulk of the time actually sailing rather than traveling to get there: the boat glides straight into Chesapeake Bay waters from the harbor. At the start and close of the charter, you pass the Hooper Strait Lighthouse, a historic screw-pile structure and one of only four remaining of its kind on the bay. The crew positions the boat for a close-up view both times.

The experience centers on what you see and hear. A friendly crew shares captivating stories about the area and sailing itself while you watch the water. Osprey and dolphins are possible sightings, though not guaranteed: binoculars are provided to help. The boat's small capacity of 13 guests keeps the deck from feeling crowded, so there's room to move and space to sit quietly if that's what you want. Life jackets, water and rain jackets are included. If the weather turns, you're covered.

Beer and wine are available for purchase if you want them. Otherwise, complimentary water keeps you hydrated. Free parking at the departure point means you don't need to hunt for a spot or pay separately. The 20% gratuity for captain and crew is built into the price, so there's no math at the end.

What’s included

• Life jackets.
• complimentary bottled water and rain jackets.
• binoculars.
• free parking at Harbour Inn.
• 20% gratuity for captain and crew.
• government fees.

Before you book

Days and timesEvery day5 departure times: the first at 09:00, the last at 14:00Last departure this season: 15 Nov

Book up to4h before

AgesAdult (18 to 64 years) · Senior (65 and older) · Youth (13 to 17 years) · Child (3 to 12 years) · Infant (under 3)

GroupPrivate

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated 5 days ago

Good to know

Low physical effortPets welcomePublic transport nearby

Operated by St. Michaels Sailing Charters

Is this one for you?Book this if you're staying in St. Michaels or arriving without a car: the boat launches from a walkable harbor location with free parking included.

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Top questions

Can children come?

Yes. Ticket types: Youth (13 to 17 years); Child (3 to 12 years); Infant (under 3).

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What is the Hooper Strait Lighthouse and why does Lady Patty pass it twice?

The Hooper Strait Lighthouse is one of only four remaining screw-pile lighthouses still standing on Chesapeake Bay. Lady Patty glides past it at the beginning and end of the charter, positioning you for a close-up view of this historic beacon both times.

Can I bring my own food or drinks aboard?

Complimentary water is provided. Beer and wine are available for purchase. Outside food and drink are not mentioned in the listing, so check directly with the operator before bringing your own.

What wildlife might I see on the sail?

Osprey and dolphins are possible sightings in Chesapeake Bay waters, though they are not guaranteed. Binoculars are provided to help you spot them if they appear.

Do I need to arrange transportation to the boat?

Free parking is included at Harbour Inn, the departure point in St. Michaels. Public transportation options are available nearby if you prefer not to drive.