Around The Town

A Guide To St. Michaels Maryland

St. Michael's

On the Water

Chesapeake Skipjack Sailing Tours

P.O. Box 582, St. Michaels, MD 21663

Experience the life of a waterman aboard the H.M. Krentz, an authentic working skipjack launched in 1955. To sail aboard the H.M. Krentz is akin to stepping back in history. There are no winches, just manpower and blocks and tackle along with the luck of a good breeze to set time back in motion. Help pull up the sails and dredge some oysters, relax and enjoy the sounds of wind and water, and learn about the ecology of the incredible Chesapeake Bay. Two hour tours are offered twice daily from April through October departing from the Chesapeake Bay Maritime Museum.

Patriot Cruises

213 N. Talbot St, St Michaels, MD 21663

A St. Michaels tradition since 1969, the Patriot is a two-level, 149-passenger ship with a fully heated and air conditioned main deck and a top deck partially covered by a canopy. During narrated historical and environmental cruises on the beautiful Miles River, guests learn about the region’s local beginnings, view historic homes and wildlife, and watch local watermen harvest clams, oysters and the famous Chesapeake Bay Blue Crab. The Patriot departs from its home dock next to the Crab Claw at the entrance of the Chesapeake Bay Maritime Museum. Cruises are offered twice daily on weekdays, and four times a day on weekends from mid-May to mid-October. 410-745-3100

Chesapeake Bay Charters - Rebecca T. Ruark

21308 Phillips Road, Tilghman, MD 21671

Enjoy a hands-on sailing experience aboard the oldest working skipjack on the Chesapeake Bay, the Rebecca T. Ruark. Built in 1886, the Rebecca T. Ruark is a perfect venue for learning about the Chesapeake Bay’s ecology, maritime history, and oyster-dredging traditions. Certified by the Coast Guard for 49 passengers, two-hour sailing cruises are offered twice daily on weekdays and three times a day on weekends. 410-829-3976

Selina II Sailing Charters

101 N. Harbor Road, St. Michaels, MD 21663

Want a truly authentic and personalized boating experience? Take a sail aboard the Selina II, a historic 41' gaff rigged cat boat. Built in 1926 as a family yacht, Selina II is operated by the original owner’s granddaughter, Captain Iris Clarke, and is the perfect setting for a nostalgic outing on the water. Selina II limits her passengers to just six guests for an intimate taste of the history of sail. Two hour excursions that include a harbor tour and a trip on the scenic Miles River are offered five times daily, departing from St Michaels Harbour Inn, Marina & Spa. 410-726-9400

Let's Go Crabbing

P O Box H, Tilghman, MD 21671

There’s no better way to experience Chesapeake Bay living than to spend a fun-filled day crabbing aboard the Riley Kat with Captain Russell Dize. A sixth generation Chesapeake Bay waterman and a Coast Guard-certified Captain, Captain Russell knows the best crabbing spots to be found. Guests learn how to crab the way countless Bay watermen have for hundreds of years—with a trotline—and get to keep all the crabs they catch. The Riley Kat sails seven days a week, twice daily from Tilghman Island. There is a six person maximum per trip. 410-886-2249

Harbour Inn Favorite = A Harbour Inn Favorite