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Enjoy a private boat party on the Calico Jack, cruising Assawoman Bay near Ocean City. Spot wild ponies and relax with friends on this 2.5-hour scenic adventure.
Enjoy a private boat party on the Calico Jack, cruising Assawoman Bay near Ocean City. Spot wild ponies and relax with friends on this 2.5-hour scenic adventure.
Book with Back Bay Adventures
Verified experiences and guided adventures in the surrounding area.
Operated by Back Bay Adventures · Ocean City, Maryland
Set sail with Back Bay Adventures aboard the Calico Jack, a spacious 48-foot headboat perfect for private boat parties and scenic cruises in Ocean City, Maryland. This 2.5-hour journey takes you through the beautiful Assawoman Bay, where you can unwind while enjoying stunning views and spotting local wildlife such as wild ponies on nearby islands. The relaxed pace provides plenty of time to socialize and soak in the natural surroundings, making it ideal for groups of friends or family celebrations. The best part is that you can bring your own food and drinks, turning your boat cruise into a personalized party on the water. Comfortable seating and ample space on the Calico Jack make it easy to move around and enjoy the breeze. Whether you're hoping to spot wildlife, enjoy the peaceful water, or simply escape the bustle of Ocean City, this private boat experience offers a unique way to connect with nature and create lasting memories with your loved ones.
easy.
2–3 hours.
No special fitness level required; accessible for all ages and abilities
Yes, Back Bay Adventures encourages you to bring your own food and beverages to enjoy during the private cruise.
The 48-foot Calico Jack comfortably holds private groups, typically up to 30 guests depending on the event.
Yes, the Calico Jack is equipped with restroom facilities for passenger convenience.
Absolutely, the cruise is family-friendly and suitable for children of all ages with proper supervision.
You can expect to see wild ponies on Assateague Island and various bird species native to Assawoman Bay.
Wear comfortable, weather-appropriate clothes and bring layers to stay cozy if the breeze picks up on the water.
Assawoman Bay has been a key waterway for local fishing and transportation since colonial times.
Efforts in the region focus on protecting the habitats of wild ponies and migratory birds through sustainable boating practices.
Back Bay Adventures is an Ocean City, Maryland outfitter that runs guided bay fishing, jet ski rentals, private charters, and pony cruises. Operating the Calico Jack headboats (40' and 48') and the Calypso catamaran-style pontoon, the company offers short, accessible outings—most 2 to 2.5-hour trips—designed for families, anglers, and small groups. Local captains provide expert, safety-focused guidance; no fishing license is required on headboat bay fishing trips, making them ideal for first-time anglers and children. Jet ski rentals use premium Seadoo models in calm, spacious riding areas with immediate ride time and brief instruction for riders of all skill levels. Private charters and boat parties allow guests to bring food and drinks, listen to their own music, and customize the route for wildlife viewing, including Assateague Island and its wild ponies. The Calypso accommodates six passengers comfortably for intimate celebrations and fishing outings. Safety equipment, life jackets, and comfortable seating are provided on all vessels, and captains give clear instructions before departure. Back Bay Adventures emphasizes punctual departures from convenient Ocean City launch points, transparent pricing, and clear reservation policies. Local guest reviews highlight professional captains, kid-friendly trips, and memorable wildlife sightings. Trips are suitable for anglers of all ages and for groups seeking scenic cruises or private boat parties. For visitors seeking short coastal experiences—flounder fishing, scenic cruises, or high-adrenaline jet skiing—Back Bay Adventures combines local knowledge with accessible, well-maintained boats and straightforward booking. Reservations are recommended during peak summer months to secure desired dates and vessel types today.
Book with Back Bay Adventures