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.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
No special fitness level required; accessible for all ages and abilities
Wildlife
History
Assawoman Bay has been a key waterway for local fishing and transportation since colonial times.
Conservation
Efforts in the region focus on protecting the habitats of wild ponies and migratory birds through sustainable boating practices.
Back Bay Adventures
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.
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.
Vessels
40', 48', Calypso
Headboats and a 6-passenger pontoon
Trip Length
1–2.5 hours
Short, family-friendly outings
Departure
Ocean City, MD
Convenient launch locations nearby
Activities
Fishing, Jet Skis, Cruises
Options for anglers and families
Reserve headboat fishing, Seadoo jet skis, private charters or a pony cruise — spots fill fast in summer.
Bring Plenty of Water
Staying hydrated during your cruise is important, especially on warm days when the sun can be strong out on the water.
Pack a Cooler with Your Favorites
Since food and drinks are BYO, bring your preferred snacks and refreshments to enhance your private party experience.
Wear Sunscreen and Sunglasses
Even on cloudy days, UV rays reflect off the water, so protecting your skin and eyes ensures a comfortable cruise.
Check the Weather Forecast
Windy or rainy conditions can affect comfort and visibility; plan accordingly for the smoothest trip.
Sunscreen
Protects your skin from strong UV rays during the daytime cruise.
summer
Hat and Sunglasses
Helps shield your face and eyes from the sun's glare on the water.
summer
Light Jacket or Windbreaker
Keeps you comfortable against wind and cooler bay temperatures.
spring
Reusable Water Bottle
Ensures you stay hydrated throughout the cruise.