THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Enjoy a private 2.5-hour fishing or cruising adventure aboard The Calypso in Assawoman Bay, Ocean City. Bring your own food and music for a relaxed and customizable outing perfect for friends and family.
Enjoy a private 2.5-hour fishing or cruising adventure aboard The Calypso in Assawoman Bay, Ocean City. Bring your own food and music for a relaxed and customizable outing perfect for friends and family.
Book with Back Bay Adventures
Verified experiences and guided adventures in the surrounding area.
Operated by Back Bay Adventures · Ocean City, Maryland
Back Bay Adventures offers an unforgettable private fishing charter or cruise experience aboard The Calypso, a spacious catamaran-style pontoon boat, cruising the serene waters of Assawoman Bay in Ocean City, Maryland. This 2.5-hour adventure is perfect for celebrating special occasions, bonding with friends, or simply enjoying a relaxing day on the water. With ample shaded seating and the option to customize your music playlist, the vibe is fully under your control as you soak in stunning Bay views. Bring your favorite food and drinks to elevate the experience aboard, while the knowledgeable captain navigates the best spots for fishing or leisure cruising. Whether you’re an experienced angler or just want a calm escape surrounded by nature, the private charter offers flexibility and comfort with a personal touch. This is your chance to try your luck at catching local species or simply unwind on a smooth, stable vessel designed for group enjoyment and privacy. The calm waters of Assawoman Bay provide a safe environment for all skill levels. Plus, it’s a fantastic way to experience Maryland’s coastal charm, combining the thrill of fishing with the pleasure of a scenic cruise.
easy.
2–3 hours.
Suitable for all fitness levels; primarily a relaxed seated experience with minimal physical exertion.
Yes, you are welcome to bring your own fishing equipment, but Back Bay Adventures also provides gear if needed.
Absolutely! You can bring your favorite snacks and beverages to enjoy during the cruise.
Yes, the trip is family-friendly and suitable for children with adult supervision.
Common catches include striped bass, bluefish, spot, and croaker, depending on the season.
All anglers over 16 need a Maryland fishing license, which you should obtain prior to your trip.
If the weather is unsafe, Back Bay Adventures will reschedule or provide a refund to ensure your safety.
Assawoman Bay has long been a vital area for local fishing and maritime commerce, integral to Ocean City's coastal community.
Efforts focus on preserving water quality and protecting local fish habitats to maintain a healthy ecosystem in Assawoman Bay.
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