Thrill-seekers and chill-seekers welcome at Bayside Boat Rentals

For eighteen years, Bayside Boat Rentals has been a staple of Ocean City and a must-visit business for anyone who enjoys being in the water. 

Walk into their island-esque shack on 53rd street, right in front of Macky’s Bayside Bar and Grill, and it won’t take long to realize that there’s truly something at Bayside Boats for everyone. For the more adventurous crowd, Bayside’s jet skis and jet boats are first-class. But for families and the laidback types who just want to take in the beautiful scenery of the bay, they have something for you, too.

“We have 14 pontoon boats, they’re all three years or newer so you can go fishing, crabbing, so you can bring a picnic, have lunch on the bay,” said Jackie Cutlip, who owns the business with her husband Chad. “We have brand new Kawasaki jet skis that we buy every summer so they’re always brand new, top-of-the-line. And then we have five-seater jet boats, they’re like little mini speed boats so whether you want to go slow or fast or just chill out and have a relaxing day, we definitely have what you’re looking for.”

On a Sunday in early July, customers rushed in and out of the store, ready to set sail on the sunny Fourth of July weekend. It was also Cutlip’s birthday. As she manned the counter inside store and took a breath after their morning rush, an employee brought her a bouquet of flowers–the environment that Bayside Boats fosters is friendly and very warm (and not just because it’s July), and as you’d expect, it’s a fun place to work. Cutlip donned beaded Mardi Gras necklaces and a fuzzy pom-pom ring, a birthday gift from her daughter. 

“We have three little girls so it’s very family-oriented around here,” she said. “Our staff is amazing, a lot of them are on their third, fourth and fifth summers. Our customers have been coming back, some of them since our kids were little babies in the office, so we have a really good clientele.” 

In their cozy air-conditioned store, life vests and t-shirts hang on the walls, as well as anchor print leggings, in all sizes, for sale. There’s a bulletin board pinned with safety guidelines, a flyer that suggests tipping your guide (“If you had a fun ride, please feel free to tip your guide! If you hear us ring the bell, that means your tip was swell!”) and a 2003 Beachcomber newspaper article about the time a tiny baby terrapin was rescued from their parking lot. 

Inside Bayside Boats
Inside the morning rush of vacationers seeking adventure.

Having been in business for almost two decades, Cutlip says she owes the success of Bayside Boat Rentals to their employees and landlords.

“My husband started [the business] with his mom and brother one year prior to me, I came in on the next summer and we’ve just kept it and changed something up every summer,” she said. “Our landlords are actually Pam and Macky that own Macky’s and we owe a debt of gratitude to them. They’re great people and they’ve helped us a lot over the years.”

She’s also grateful for Bayside’s repeat customers, of which they’ve gained many over the years. 

“We’re just trying to make it, little small business people, but we’re really proud of our employees and what they do here. We think we have a great staff and we appreciate the people that come in and give us their business and trust us.”

Over by the water, five-year Bayside Boats veteran and jet ski guide Brian Rafer sent a crew of ski renters out on the bay after talking to them about jet ski operation and safety. 

“Come out, rent a jet ski for an hour, rent a pontoon for four, it’s a good old time,” Rafer said. “Just go out there on the water and have some fun.”

Bayside Boats jet ski garage
The mural-ed garage where jet skis are stored.

Most of the employees are obviously passionate for water sports, and they’re plenty friendly and helpful to visitors who arrive for a spontaneous boat ride. Still, Cutlip has just one piece of advice for potential customers. 

“We recommend reservations. We get pretty busy here so it’s always best to reserve it in advance, and you can just do that over the phone with a credit card, it’s simple, just takes a few minutes,” she said. “We have free parking until six p.m. We have drinks, ice, bait. Anything that you need, we have it.”

Outside Bayside Boats
Treat yourself to a day of thrill, relaxation, or both, at Bayside Boat Rentals.
Kristin is a writer and photographer in Ocean City, Maryland, and is the content manager for and other State Ventures, LLC sites. She loves getting reader-submitted stories and photos, so send her an email anytime. She also works part-time at the Art League of Ocean City and the Ocean City Film Festival and lives just off the peninsula with her dog and fiancé. Her photos can be found on Instagram @oc_kristin.

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