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St. Michaels Sailing Charters

5.0 • 1.4K reviews

St. Michaels Sailing Charters invites guests to experience the Chesapeake Bay aboard two distinctive yachts: the historic 1935 Maryland-built ketch Lady Patty or Epiphany, a spacious 44-foot luxury catamaran. Owners GM and Laura B...

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St. Michaels Sailing Charters

5.0 • 1.4K reviews

St. Michaels, MD

Book St. Michaels Sailing Charters

Historic Ketch Sailing Lesson in St. Michaels

Take the Helm and Learn Hands-On Sailing Skills

$1,377.08

2-Hour Sailing Lesson in St. Michaels

Build Practical Sailing Skills With Private, Hands-On Instruction

$1,377.08

2-Hour Beer Tasting Cruise in St. Michaels

Savor rotating craft beer tastings aboard the historic Lady Patty

From$186person

Private Half-Day Sailing Charter in St. Michaels

Harbor views and wind-powered sailing on the Miles River

$2,899.48

2-Hour Chesapeake Bay Sailing Cruise

Sail the Miles River aboard a spacious catamaran

From$269person

Full-Day Private Sailing Charter in St. Michaels

Private catamaran sailing with harbor views and Miles River breezes

$3,453.08

Sunset Champagne Cruise in St. Michaels

Sail a historic ketch at sunset with champagne and Chesapeake Bay views

From$159person

Marriage Proposal Cruise in St. Michaels

Plan a private proposal aboard a historic 1935 ketch

$2,069.08

What people are saying

We had a great time out on the water with Rob (captain) and Steph. They not only sailed us around the Miles River, but also shared a general history of St. Michaels and the area. It was an enjoyable trip, and we would happily do it again!