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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

$1,238.68

2-Hour Beer Tasting Cruise in St. Michaels

Savor rotating craft beer tastings aboard the historic Lady Patty

From$159person

Private St. Michaels Sailing Charter

Harbor views and wind-powered sailing on the Miles River

$2,345.88

2-Hour Chesapeake Bay Sailing Cruise

Sail the Miles River aboard a spacious catamaran

From$242person

7-Hour 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

$1,377.08

What people are saying

We had the most fabulous sunset cruise with the Selina II! Iris and her first mate, Matt, where the best. We were worried that our sail might be cancelled because of the hurricane winds and the rain, but the day ended up clearing and the sun came out for a breathtaking sunset. Even though we have lived in St. Michael's for 13 years, we learned so much that we never new about the area. It was truly a delight and would highly recommend to both locals and tourist!