Sightseeing Charters & Tours

Sit back, relax, and let someone else take the wheel on these guided tours. You will see gorgeous scenery and learn about the Chesapeake Bay along the way!

Nathan of Dorchester SkipJack

The Nathan of Dorchester offers visitors a unique opportunity to experience the vanishing skipjack heritage of Maryland’s Eastern Shore. Since the 1880s, skipjacks have sailed the Chesapeake Bay. While there once were as many as 800 or more of these beautiful vessels, today fewer than two dozen of the original dredge boats remain. Only a handful still dredge for oysters, the last remnant of America’s only surviving commercial sailing fleet.
Location: Long Wharf at the end of High Street, Cambridge, MD 21613
Phone: 410-228-7141

Seawolf Oufitters

Evening Cruises: Departs Oxford or Bellevue Ferry Locations on Tred Avon River (Other departure sights available including your vacation home) Sightsee the Tred Avon & Choptank River Non Alcoholic Refreshments Provided-BYOB Rates: 150 per Hr-2 Hr. Minimum –Includes Fuel Half Day Chesapeake Bay & Choptank River Excursions Flexible venue & destinations: Options include Historic Waterfront Villages & Resorts Rates: $600 plus fuel
Phone: 443-786-4418
Skipjack H.M. Krentz

Skipjack H.M. Krentz

Enjoy a relaxing, educational, and unforgettable sailing tour on Chesapeake Bay waters on the historic Skipjack H.M. Krentz. Offering catered picnics, cocktails and hors d’oeuvres, or bring your own food and beverages. Dress as comfortably and casually as you like. The H.M. Krentz is an authentic working skipjack and one of the newer vessels to be built for the rigors of Maryland’s wintertime commercial oyster dredging fishery. Launched in 1955 in Harry Hogan, Va., by the Krentz Shipyard for Capt. David Lewis of Wingate, Md., The H.M. Krentz is 49 ft. length on deck, 70ft. length overall.
Location: 304 Burns St, St Michaels, MD 21663
Phone: 410-745-6080
Skipjack Rebecca T. Ruark

Skipjack Rebecca T. Ruark

Come aboard a national historic landmark. Set sail on the oldest working skipjack on the Chesapeake Bay, built in 1886. Enjoy nautical tales and ecology stories from 5th-generation and world-renown Capt. Wade H. Murphy, Jr. Capt. Wade personally takes you on a 2-hour sail 7 days a week. Saturday and Sunday (11-1, 2-4, 6-8 sunset) and Monday through Friday (11-1, 6-8 sunset). Private group charters available. The vessel is U.S. Coast Guard certified for 49 passengers.
Location: 21308 Philips Road, Tilghman Island, MD 21671
Phone: 410-886-2176
Patriot Cruises

Patriot Cruises

The Patriot is a two-level, 149-passenger cruise boat with the main deck fully heated and air conditioned and the top deck partially covered by a canopy and partially open to the stars for 4th of July fireworks or sunset cruises. The Patriot departs from their home dock next to the Crab Claw at the entrance of The Chesapeake Bay Maritime Museum. You may walk down Cherry Street from Talbot Street (the St Michaels main street) or park in the Maritime Museum parking lot.
Location: 213 N. Talbot Street
Phone: 410-745-3100
Chesapeake Lights Lighthouse Tours

Chesapeake Lights Lighthouse Tours

Aboard the M/V SHARPS ISLAND, you will be taken back through the storied history of the Chesapeake Bay and its lighthouses. Four different Chesapeake Lights trips accommodate any schedule and all levels of interest. Each includes a narrated recounting of the Bay`s history, as well as informed local insights about its fragile and beautiful ecosystem.
Location: 5907 Tilghman Island Road, Tilghman Island, MD 21671
Phone: 410-886-2215

Lady Patty Classic Yacht Charters

Lady Patty is a 1935-built offshore sailing yacht that departs up to three times daily from Tilghman Island for the beautiful Chesapeake Bay. Guests are treated to a true sailing experience on public sailing excursions and private charters. Immerse yourself in the thrill of sailing aboard a true classic from the golden age of yacht racing. While underway, you will be surrounded by varnished teak, polished bronze and yards of towering sails. Drink service is available on all charters including bottled water, soft drinks, craft beer, wine and featured cocktails including our fresh-squeezed lime juice margaritas.
Location: 6176 Tilghman Island Road, Tilghman Island, MD 21671
Phone: 410-886-1127