Where do we check in?

Check in at Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663 and arrive 15 minutes before your scheduled departure.

How many guests can join?

Private charters accommodate a maximum of 13 guests, which keeps the experience intimate and flexible.

Are there age or alcohol restrictions?

Yes—alcohol service is limited to guests 21 and older; everyone else can still enjoy the cruise.

What is included in the charter price?

The charter includes private use of the Lady Patty for two hours and complimentary champagne; applicable amusement tax and crew gratuity are added on.

Can we customize the route or request sunset timing?

Yes—the crew can tailor the pace and suggest timing for sunset sails or calmer anchoring spots for photos.

What is the cancellation policy?

Specific cancellation terms are set by the operator; confirm when booking as policies vary for private charters.

Champagne Sail on Lady Patty: Private Bachelorette Cruise in St. Michaels | Private | Sailing

Onboard the Lady Patty, a historic 1935 ketch, a private two-hour charter turns a bachelorette or bachelor party into an intimate coastal celebration. The experience launches from Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663, and sweeps you past the low marshes, wooden bulkheads, and mirrored glass of Chesapeake Bay as the crew pops a bottle of champagne for the group. From the first furl to the last toast, the feeling is equal parts maritime history and uncomplicated fun. St. Michaels sits on Maryland’s Eastern Shore, a small town with a long connection to the water. The Lady Patty’s classic lines and oak interior give the boat a lived-in elegance that feels right at home among local crab shacks and sailing schools. This is a private charter for up to 13 guests, so the rhythm of the trip is relaxed: gentle sailing, conversation, and room to move without the crush of a large tour boat. Key features of the outing include the 1935 ketch itself, sweeping Chesapeake Bay views, and an intimate group setting with complimentary champagne to mark the celebration. Natural highlights include salt marshes of spartina grass, historic stone bulkheads, and the chance to spot osprey and great blue heron working the shallows. The bay’s geology—shallow estuary channels carved by tidal flows—creates long, placid vistas ideal for watching light shift as the boat glides. Why book this trip? It’s an antidote to loud bar scenes: private, photogenic, and timed to focus on people rather than a packed schedule. The Lady Patty is a standout in the local recreation scene because she’s both a working sailboat and a piece of maritime history—built in 1935 she offers a tangible link to the Chesapeake’s sailing past while operating as a modern charter. Practicalities are straightforward: arrive at the dock 15 minutes before departure; the charter runs two hours and accommodates adults 21 and older for alcoholic service. Pricing begins at $995 for private charters, with applicable taxes and crew gratuity. Because groups are small, the crew can tailor the pace: linger near a quiet shoreline for photos, or head into open water for stronger wind and more pronounced heel. This trip suits anyone who wants celebration without spectacle—friends who prefer good conversation, coastal light, and the tactile pleasure of canvas and teak. For couples and groups seeking memories that balance intimacy, history, and the Chesapeake’s low-angled light, a champagne toast aboard the Lady Patty is hard to beat. Bookers should note the minimum age and the private-charter pricing; the crew welcomes questions about timing for sunset sails and will advise where to anchor for the calmest water and the best group photos against historic town piers nearby docks.