Your vacation isn't complete without spending some time on the glistening water of the Chesapeake Bay. These Eastern Shore watersports are some of the best ways to do it! Check out our local tips on boat charters, marinas, jet ski rentals, and more so you can explore the Bay like a pro. Then, find your ideal property and get one step closer to enjoying all of these exciting Eastern Shore activities on the water. We have a wide variety of vacation rentals to help you explore the beauty of the Bay!

Helpful Guides

Get all the information you need right at your fingertips with these handy guides. They are full of tips on where to go, what you will see, and how to get there!

Kayak, Paddleboard, and Boat Rentals on the Eastern Shore of MD

However you prefer to get out onto the water, we can help you get there. See some of the best spots for boat rentals on the Eastern Shore of MD, and hit the water in style. Before you go ahead and rent, though, check out some of our Eastern Shore vacation rentals. Many of them include complimentary kayaks and paddleboards for you to use during your stay!

Easton Cycle and Sport

Easton Cycle and Sport is another fantastic company for boat rentals on the Chesapeake Bay`s Eastern Shore. Friendly owners Ryan and Julie Hickey happily provide kayak, canoe, and paddleboard rentals all year long. So, no matter when you visit, you can cruise the shore in style. They offer convenient options for one-day, three-day, and full-week rentals with a fantastic selection in store.

723 Goldsborough Street, Easton, MD 21601

(410) 822-7433

Dockside Boat Rentals

Are you looking to hit the water in the Oxford, MD, area? Dockside Boat Rentals has everything you will need. They offer single and tandem kayaks, high-quality Hobie paddleboards, and Yamaha WaveRunners for up to three passengers. They have complimentary local delivery, and all of your safety equipment is included! If you ever have an issue, they are happy to assist you 24 hours-a-day.

104 W. Pier Street, Oxford, MD 21654

(410) 652 - 6533

Shore Pedal and Paddle

You can`t go wrong with Shore Pedal and Paddle for your boat rentals in St. Michaels, MD. They offer free delivery or pick up for bikes, kayaks, and stand-up paddleboards. Flexible plans range from hourly to full-week rentals with lessons and guided tours available. Are you interested in purchasing one of their kayaks or paddleboards? Rent it first, and if you like it, they credit the rental cost toward the purchase price!

500 S. Talbot St, St Michaels, MD

(410) 745-2320

Schnaitman's Boat Rentals

Schnaitman`s Boat Rentals is conveniently located on the Wye River and public boat ramp, so you can rent your boat and immediately start your adventures on the water. They offer daily rentals for motorboats and rowboats on a first come, first serve basis. If you are planning a fishing trip, feel free to pick up snacks and supplies from their bait shop!

12498 Wye Landing Ln, Wye Mills, MD 21679

(410) 827-7663

Chester River Kayak Adventures

If you are searching for some of the best kayak tours on the Eastern Shore, we highly recommend Chester River Kayak Adventures. Their half-day tours guide you through scenic waterways and offer glimpses of local wildlife. You will even get to check out some secluded beaches along the way! If kayaking isn`t your thing, you are welcome to rent stand-up paddleboards and sailboats instead.

5758 N Main St, Rock Hall, MD 21661

(410) 639-2001


Whether you are launching a boat or you simply need a place to rest and refuel, there are plenty of marinas on the Eastern Shore. Find the best one near you!

Brewer Oxford Boatyard and Marina

402 E. Strand, Oxford

(410) 226-5101

Campbell`s Boatyards

Bachelor Point
26106 Bachelor Harbor Drive, Oxford, MD 21654
(410) 226-5592

Town Creek
109 Myrtle Avenue, Oxford, MD 21654
(410) 226-0213

Jack`s Point
106 Richardson Street, Oxford, MD 21654
(410) 226-5105

Easton Point Marina

975 Port Street, Easton

(410) 822-1201

Higgins Yacht Yard

203 Carpenter Street, St. Michaels

(410) 745-9303

Knapps Narrows Marina

6176 Tilghman Island Road, Tilghman

(410) 886-2720

Lowe's Wharf Marina

21651 Lowe's Wharf Road, Sherwodd

(410) 745-6684

St. Michaels Marina

305 Mulberry Street, St. Michaels

(410) 745-2400

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.

Long Wharf at the end of High Street, Cambridge, MD 21613

(410) 228-7141

Seawolf Outfitters

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


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 doeuvres, 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.

304 Burns St, St Michaels, MD 21663

(410) 745-6080

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.

21308 Philips Road, Tilghman Island, MD 21671

(410) 886-2176

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.

213 N. Talbot Street

(410) 745-3100

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.

5907 Tilghman Island Road, Tilghman Island, MD 21671

(410) 886-2215

Lady Patty 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.

6176 Tilghman Island Road, Tilghman Island, MD 21671

(410) 886-1127