Places to Play

Hilda M. Willing Skipjack Tours

Two-hour sailing tours aboard a 1905 historic Chesapeake Bay skipjack.

  • 410-924-9975
  • Tilghman Island, Maryland 21671
Lady Patty Yacht

Lady Patty Classic Yacht Charters

A 1935-built offshore sailing yacht that departs daily; offering drink service including craft beer, wine and fresh-squeezed lime juice margaritas.

  • 410-886-1127
  • Tilghman Island, MD 21671

Sail Selina II

Tours for six aboard vintage 41-foot 1926 sailing yacht; offering two-hour day sails and romantic sunset champagne cruises from Harbour Inn & Marina.

  • 410-726-9400
  • St. Michaels, MD 21663

Skipjack H.M. Krentz

Relaxing and educational sailing aboard historic skipjack; offering day sails, plus catered picnics, cocktails and hor d’oeuvres, or you can BYO food and beverages.

  • 410-745-6080
  • St. Michaels, MD 21663

Skipjack Rebecca T. Ruark

Two-hour sails and private group charters aboard the oldest working skipjack on the Chesapeake; offering nautical tales and ecology stories from fifth-generation waterman.

  • 410-886-2176
  • Tilghman Island, MD 21671

Winnie Estelle

45-minute cruises, private charters, and educational tours aboard historic 1920s buyboat on the Miles River with up to 32 passengers, May through October.

  • 410-745-2916
  • St. Michaels, MD 21663
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