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A Day on the Bay with Bayside Boat Rentals

Why Rent a Pontoon Boat?

There’s no shortage of boats out on the bay around Ocean City. Some are privately owned, but others are rented. Lazing away the days on the beach is great, but if you are looking for something a little different, something that brings the family together and can be as active or passive as you wish, then renting a boat for a couple of hours, or even a day, seems like a good idea. Since the thought of renting a pontoon boat may feel a little daunting to some, we decided to give it a try, and see just how easy it is.
Bayside Boat Rentals on 53rd Street

Why Bayside Boat Rentals are the Best of Ocean City®

We headed straight to family run Bayside Boat Rentals on 54th street, right next to Macky’s. They are known for their pontoon boat rentals, as well as their jet ski rentals. In fact, Bayside Boat Rentals has won Best Boat Rental in the Best of Ocean City® for 2023, and in many previous years too. Chad and Jackie Cutlip, the owners, have run the business for some 20 plus years. Along with their 3 children who have grown up behind the counter in the office and are now teenagers, they have around 15 employees each season, many of whom have worked with them for years; a testament to the great working environment at Bayside Boat Rentals. Chad and Jackie keep in touch with old staff, attend their weddings, hold their babies and see them while on family vacations!  They run their business and treat their staff and customers just like they run their household, says Jackie, “… with respect, honesty, fairness and tons of laughs!” 

How it all began

It all started in 1999, when Chad’s mom took a chance and bought a pre-existing business, knowing nothing about the industry, and gave it a go with Chad and his older brother.  After several years of ups and downs and another owner change, Chad and Jackie purchased it out right. It has been the two of them putting their hearts and souls into the business, and never giving up since then.  They have built Bayside Boat Rentals into what it is today. Many have helped along the way, and if you read their reviews, you will see just why they are the Best of Ocean City® for boat rentals. 

Owners of Bayside Boat Rentals, Chad and Jackie Cutlip


How easy is it to rent a pontoon boat?

Bayside Boat Rentals operates on a reservation-only basis, and they have been at this for so long that they have the check-in process down to a science! The driver must be at least 18 years of age with a valid driver’s license to operate the boats or jet skis.  The pontoon boats are very easy to maneuver and are on the slower side which makes them very easy for new drivers. The staff at Bayside Boat Rentals give PLENTY of instructions to safely operate the boat, and, on our visit, Jason went through everything you could possibly need to know. There is also the reassurance that Bayside Boat Rentals is only a phone call and a few minutes away should anyone need assistance during their rental.  The boats are capable of holding 8-12 passengers, as long as your entire party is UNDER the coast guard approved weight limit on the boat, so when renting, make sure you have an accurate head count at time of booking. 

Getting all the paperwork completed before heading out to the boat
Instructions on driving the boat safely are given on and off the boat before you take it out
Jason, one of the Bayside Boat Rentals crew, going over the details

Where to go once you are out on the Boat?

When you rent your pontoon boat from Bayside Boat Rentals, you have 7 miles of beautiful bay to explore.  The rental locations is in mid-town Ocean City on 54th street, and you can go as far south as the RT 50 bridge, (but not past it).  You can go as far north as the Delaware state line and the RT 54 bridge at Harpoon Hannas, and everywhere in between! Watch out for the sandbars near the Rt50 Bridge when the tide is low, it’s possible to get stuck on them!

You can have a relaxing day of fishing, crabbing or just cruising the bay. Bring a cooler and have a picnic on the water. We stopped on the St Martin River, by a little sandy cove, anchored the boat and took a swim. We weren’t the only ones doing this, it seemed a popular spot to relax. 

A sandy cove on the St Martin River, perfect for a swim
under the Rt90 Bridge

We also took the boat down some of the canals in North Ocean City where there were plenty of beautiful houses lining the waterways.  We picked out the ones we would want to own if we ever won the lottery! 

The quiet bays lined with beautiful houses

Bayside Boat Rentals buys new boats every year, so their entire fleet is in great shape and all of their equipment is always properly maintained. Our boat was clean and in perfect working order. Our driver thoroughly enjoyed his time behind the wheel, and the rest of our party felt like we were living the life, as we sat back with the wind gently blowing our hair and took in the sights! 


Bayside Boat Rentals have a saying, ” BAYSIDE 4 LIFE,”  and once you join their family, you are in it for life!  Whether you work for them, or rent from them, you will certainly want to keep coming back!

Here’s how to vote for Bayside Boat Rentals for this years Best of Ocean City®


See more of our day out on the water with Bayside Boat Rentals here.

Anne grew up in Edinburgh, Scotland, and came across Ocean City for the first time over 30 years ago and shortly after it became her permanent home.  When time allows, Anne still loves to travel. She has been with OceanCity.com since September 2014.

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