Our Guide on How to Cruise the Bay

This guide on how to cruise the bay will give you insight on where to rent your craft, where to launch, and who to hire for a well-rounded trip, whether using your own power or letting a captain steer the way.

How to Cruise the Bay: Rent Your Own Craft

To enjoy a perfect sunrise or sunset, do a spot of fishing, or just cruise about, choose when to go and where to launch by renting your own canoe, kayak, or paddleboard to watch the sun rise or set from the water.

Our Guide on How to Cruise the Bay


Easton Cycle and Sport

Rent high quality kayaks, canoes, and SUPS from this dog-friendly shop. Bonus: They also rent tandem kayaks.  723 Goldsborough Street; 410-822-7433.

Easton Point Marina and Boatyard

Anchored along Easton’s only public waterfront, you can rent kayaks, paddleboards and boats so you can set off on your waterfront adventure seamlessly. 975 Port Street; 410-822-1201


Shore Pedal & Paddle

This St. Michaels mainstay is open during the warmer weather, but a responsive hands-on owner will get you what you need any time of year. Bonus: They offer seasonal sunset tours and even the occasional sunrise tour of local waterways.  500 S. Talbot Street, St Michaels; 410-745-2320.


Tilghman Island Marina and Rentals

You can launch from a floating dock ramp right out front or have your canoes and kayaks brought to you.  (They also rent pontoon boats). Bonus: They will help steer novices to tranquil waters and experienced paddlers toward more adventurous water routes.  6140 Mariners Court; 410-866-2500.


Dockside Boat Rentals

This full service boat rental company delivers to your dock! Their rental fleet includes Zodiac center console boats that let you ride in safety and comfort. 410-251-8802

Pro Tips on Where to Launch

Whether you bring your own kayak, canoe or SUP with you on your visit to Talbot County or whether you choose to rent locally, there are many magical spots on the water where you can take in sun up, sun down or simply a sense of serenity. Here are some pro tips collected from locals that will make your launch smooth:

The marina at Easton Point in Talbot County, Maryland, in Our Guide on How to Cruise the Bay

From Easton: There are two popular launches. The Miles River Bridge Landing on Unionville Road used to be a boat ramp, but now is used exclusively for soft launches. Easton Point currently functions as a traditional boat ramp, though the marina provides an unhurried launch for a peaceful paddle on the Tred Avon River. 941 Port Street.

From St. Michaels: There’s both a floating dock and a soft launch from Back Creek Park, tucked into a quiet residential neighborhood, leading to the Miles River. 301 Chew Avenue. You can map your route, with our St. Michaels Water Trail Map.

From Oxford:  A small public beach adjacent to the Tred Avon Yacht Club is a prime spot to push off into Town Creek and beyond. Near 102 W. Strand Road.

From Tilghman: Dogwood Harbor is home to a busy marina active with fishing boats. Kayaks must launch from the main boat ramp that leads to the Choptank River. However, within minutes of launch you will be rewarded with beautiful Chesapeake Bay views. Dogwood Harbor Road. You can map your route using our Tilghman Island and the Bay Hundred Water Trails Map.

How to Cruise the Bay: Boat with the Best on a Tour or Cruise

Book a ride with one of Talbot County’s many local captains for an unforgettable sunset. As a local saying goes, “You haven’t seen Talbot County until you’ve seen it from the water.”

Sailboat tour in Talbot County, Maryland, in Our Guide on How to Cruise the Bay

Sail Selina II

If you’re feeling a little Gatsby-esque, book a scenic champagne sunset cruise along the Miles River on the Selina II, a beautiful yacht crafted with mahogany and brass details that’s been in Captain Iris’s family since 1926. 101 N. Harbor Road; St. Michaels; 410-726-9400.

The Inn at Perry Cabin

A sunset to impress is delivered by the ultra-glam fleet of yachts (under sail or motor, your choice) from the luxury resort Inn at Perry Cabin. Sundown hors d’oeuvres and cocktails never tasted better. You need not be a resort guest to book a private charter. 308 Watkins Lane; St. Michaels; 410-745-2200

Patriot Cruises

You’ll get a dash of history with a scenic sunset cruise on this stately cruiser painted in red, white and blue, which seats 149 and has a full bar. Wrapround decks ensure a great sunset view no matter where you perch. 213 N. Talbot Street, St. Michaels; 410-745-3100.

St. Michaels Harbor Shuttle

A water taxi that typically ferries folks to and from popular sights and restaurants on the Miles River and connecting waterways also offers a one-and-a-half-hour sunset tour. Feel free to BYOB (bottle) and BYOD (dog).  Located at the end of Mulberry Street beside Blu Miles Restaurant, St. Michaels; 410-819-9606.

Love and Dreams Tiki Bar Boat

A chill hour-and-a-half is guaranteed on this sunset tour. Nearly half of the boat is given over to a tiki bar with thatched canopy. Order tropical drinks while noshing on complimentary appetizers. Located at the end of Muskrat Park (next to Foxy’s Harbor Grill), St. Michaels; 410-844-4400.

Oxford-Bellevue Ferry

Hop aboard the oldest continuously operating ferry in the United States (circa 1683), which traverses the Tred Avon River. You can bring your car, your bike or your own two feet to watch the sun sink into the Chesapeake Bay on the final 10-minute crossing of the day.  Bonus: Pedestrian passengers pay just $5 for a ride.  27456 Oxford Road, Oxford; 410-745-9023.

Tilghman Island Marina and Rentals

Prized among sunset connoisseurs and photographers, the Sunset Drifts Tour only runs when sundown promises to be something special. Bonus: You can bring dogs, snacks and drinks on board with zero hassle. Tilghman Island Marina, Dogwood Harbor Marina, Tilghman Island; 410-924-9575.

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