Ocean City, Maryland Bay Charter Service

Explore the back bays of Ocean City, Maryland on a private boat. From fishing to sightseeing, our Captain wi provide a tailored experience. Plenty of horsepower to get to the perfect location.

“We do what you want”

Whether it be a secrete fishing hole or bouncing from bar to bar. Enjoy the finest sunsets in Maryland on our evening excursions or wake up early and get a jump on the fish. Catering to both family fun and experienced anglers, the Dirty Monkey has it all. 


Ocean City Family Fun

Before your trip, Captain Josh Wentling will map out each experience that includes as many activities that time permits. When it comes to entertainment for the little ones, Ocean City family fun is the name of the game! Captain Josh Wentling is a US Coast Guard-licensed charter captain and does not skip a beat when it comes to your families safety. Prepare for a great time with plenty of opportunities to “Monkey Around”!


Fish – Crab – Clam In Ocean City

Experienced in the fishing industry, Captain Josh has been hunting the waters from Hatteras, NC to Ocean City, Maryland . When it comes to the big boats he has won and placed in many major tournaments up and down the Atlantic Coast and has a reputation for fishing success. With a lifetime of experience, you can be assured that he will find the best places in Ocean City, Maryland to find the fish, crabs and clams!

Tell Me More

Ocean City Eco Tours and Photography

Set out on your private bay charter to see and photograph wildlife. Our captain wills here his knowledge about the flora and fauna, marine life and bird life while you get a close up view of it all. Take some stops on an Ocean City sandbar or one of Assateague Islands many sandy shores to pick shells and find unique reminders of nature such as egg cases and sand dollars. The boat can travel in shallow water so bring some bug spray and wind down narrow marsh ways and tributaries the main bay areas. These trips are photographers dream. Click after click of ponies on the bayside, ospreys nesting, herons and pelicans feeding and sometimes porpoises and seals. A great tour of the bay for both families and professional photographers.

Say Cheese

Ocean City Adult Entertainment

Get your mind out of the gutter but don’t stiffen up just yet!
The Dirty Monkey did not get its name for nothing. Take your KNOTY crew on the bay for the ultimate Booze Cruise! Plenty of photo ops to be had along the way as you Captain safely hits as many dockside venues as possible. Make sure to ask about our “Poker Run”! 


Ocean City Sunsets and Date Nights

Impress your honey or the whole family with a sunset cruise in Ocean city, Maryland. Take you camera and make sure to send us one of the 3000 photos you take on your trip! Plan your trip around the sunset and let your captain know what you want to do while you are on the water. Fish, swim, clam or cruise. Have dinner ready for you to take on the boat from Hoopers Crab House (Onsite) and plan a romantic picnic on the sandbar. Hop across the bay to one of Ocean City’s bayside restaurants for a cocktail. Make you way down the coastline of Assateague Island and get that perfect shot. Whatever you decide to do, you’re going to love it!

Toast the night away


Ready set go! Set sail for the grand tour of Ocean City by boat on your private charter. Visit marinas hosting huge sport fishers, discover real estate on the water, check out the commercial harbor, shoot the inlet on colder days and see all the wildlife OCMD has to offer. Make some stops on the way as well. Grad a drink from a bayside bar and grab a bite to eat. Hop off in some sandy shallow water for a swim. So much to see and do.


The Charter Boat

Hop aboard the skiff! Manufactured by Sundance Boatworks, this 20′ flat bottom has the ability to go places other boats can not. Easily maneuvering through the deep Chanels to the shallows of the back tributaries. Perfect for getting our charters up close and personal to wildlife, and through areas less traveled.