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 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
- 100% Non Smoking
- Bridal
- Dinner
- Marine/Boating
- Outdoor Activity
- Outdoor Dining
- Pets Allowed
- Sailing Lessons
- Waterfront Dining
- Weddings
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
