Leave the navigating to us. Whether you’re in the mood for sipping champagne on a sunset cruise, trying your hand crabbing alongside a local waterman, learning about the history and heritage of the Chesapeake Bay, or simply relaxing as you take in the sights aboard a luxury yacht, Talbot County’s boat captains and their diverse vessels are ready to ferry you on your dream journey.

Harbor Shuttle & Tours

Water taxi service and harbor tours, offering an up-close look at the ospreys and many other sea birds and ducks.

305 Mulberry St., St. Michaels


Hilda M. Willing Skipjack Tours

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

Dogwood Harbor, Tilghman Island


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


Let’s Go Crabbing

Fun-filled crabbing tours aboard the Riley Kat with a sixth-generation Chesapeake Bay waterman and a Coast Guard-certified captain.

Severn Marine, Tilghman Island


Miss Arielle Charters

Specializing in crabbing, fishing, hunting, and Chesapeake Bay heritage tours for up to six; guests can take home a half bushel of crabs each.

Dogwood Harbor, Tilghman Island


Patriot Cruises

Cruises of the Miles River aboard a two-level 1930s steam ferry replica, offering insight about area history, historic homes, wildlife, and the local seafood harvest.

213 N. Talbot St., St. Michaels


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


Winnie Estelle

Offering 45-minute cruises, private charters, and educational tours aboard historic 1920s buyboat on the Miles River, with up to 32 passengers, May-October.

213 N. Talbot St., St. Michaels


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.