Sailboats and the Chesapeake Bay are a classic combination. There’s nothing quite like being beneath billowing sails as you explore our waterways. Talbot County’s fleet of sailboats offers you a chance to slow down and soak in our stunning scenery. If you’re inclined, many boats will encourage you to hoist a sail or take the wheel. Should you find the experience irresistible, there happens to be no better place to take sailing lessons than right here.

Hilda M. Willing Skipjack Tours

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

Dogwood Harbor, Tilghman Island


Inn at Perry Cabin by Belmond

Whether setting off on a tranquil chartered cruise or learning new skills on an in-depth sailing course, our fleet of luxury sailing vessels are sure to make a splash. For enquiries contact our Boating Concierge by calling 410-745-2200 or emailing

308 Watkins Lane, St. Michaels


Lady Patty Classic Yacht Charters

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

6176 Tilghman Island Rd., #5, Tilghman Island


Selina II

Upscale and exclusive tours for just six guests aboard the vintage 41-foot 1926 sailing yacht Selina II, with two-hour day sails and romantic sunset champagne cruises from the St. Michaels Harbour Inn & Marina.

101 N. Harbor Rd., St. Michaels


Skipjack H.M. Krentz

Relaxing and educational sailing aboard historic skipjack; offering two-hour sails and all-day charters. Bring your own food and beverages.

213 N. Talbot St., St. Michaels


Skipjack Rebecca T. Ruark

Two-hour sails and group charters aboard the oldest working skipjack on the Chesapeake; enjoy nautical tales and ecology stories as told by a fifth-generation waterman.

Dogwood Harbor, Tilghman Island


Boaters—and those who love the life on the water — have ranked this among their favorites for generations.  The pristine waterfront offers spectacular views of beach, marsh, fields, and forests, along with historic mansions.

Talbot County is always upping its game. Those traversing the Chesapeake Bay will be thrilled to know that the Army Corp of Engineers recently dredged Knapps Narrows, the channel that separates Tilghman Island from the mainland and provides a welcome shortcut to Oxford.  Plus, Talbot County offers two (free) waterfront trail maps that will make your exploration of the area’s waterways a dream. You can find them at

It’s no surprise that many high quality waterfront events take place here, including the 2018 Star World Championship sailing regatta that will draw the best sailors from around the world. These races will be hosted by the Tred Avon Yacht Club in Oxford from October 5-15, 2018.

Whether you have a yacht or a powerboat, you’ll find a comfortable home here. The area boasts many full-service marinas and high quality maintenance facilities, historic towns, and waterfront attractions.

Don’t have your own boat?  No problem. The nautical lifestyle isn’t reserved for those captaining their own boats.  Talbot County is home to many outfitters who can provide kayaks, canoes, and paddleboards for the day so visitors can explore the waterfront.  Plentiful gentle tributaries and rivers mean you need not power through to experience the best of what the area offers. Paddling allows you to slow down and soak in the natural wonders.  

For visitors looking for a waterfront experience without breaking a sweat, no worries.  We’ve got you covered. Sailboats, yachts and working fishing boats can guide you along Talbot County’s waterways.  Or you can hop aboard The Oxford-Bellevue Ferry, the country’s oldest continuously operating ferry, which this year happens to be celebrating its 335th anniversary.  For just a few dollars you can board the ferry—on foot or with your car— and cross the Tred Avon River from the scenic small town of Oxford to the charming hamlet of Bellevue as you take in wide water views, along with glimpses of heron, osprey and bald eagles.

To learn more about the water, the people who work it and the boats that that ply it, head to The Chesapeake Bay Maritime Museum in St. Michaels, one of the finest of its kind in the world.  While there, you can explore a distinctive screwpile lighthouse to get a sense of the spartan and difficult life lighthouse keepers led. And for a hands-on experience, you can even participate in a restoration of a vintage vessel in an “Apprentice For A Day” program.

And no matter what you do, don’t miss a chance to dine at one of Talbot County’s fabulous restaurants, where you can enjoy the fresh crab, oysters, rockfish, skate, and other seafood plucked straight from the water surrounding you.