Places to Play

Chesapeake Lighthouses Tours

Four different trips accommodating all levels of interest with narrated history and lighthouse tales, as well as local insights about the Bay’s fragile and beautiful ecosystem.

  • 413-835-1630 / 410-745-8130
  • Tilghman Island, MD 21671

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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