Private Boat Parties & Cruises in Ocean City, Maryland
Difficulty
easy
Duration
2–3 hours
Fitness Level
No special fitness level required; accessible for all ages and abilities
Overview
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.
Private Boat Parties & Cruises
1.5 hr. $575 | 2.5 hr. starting at $725| Celebrate a special occasion
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Adventure Photos
About This Adventure
Experience an unforgettable private boat party aboard the Calico Jack, a spacious 48’ headboat. Enjoy a scenic 2.5-hour cruise through Assawoman Bay, spotting wild ponies and wildlife while relaxing in comfort. Bring your own food and drinks, and create lasting memories with friends in a stunning coastal setting.
Starting May 17th, the Calico Jack will be running private 1.5 and 2.5 hour cruises! You can bring up to 32 friends and family on your private excursion!
Celebrate a special occasion!
Rates
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Private 1.5 hr. Cruise (Bring up to 32 people): $575
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Private 2.5 hr. Cruise (Bring up to people): $725 (off-season) $950 (peak-season)
Duration | Times
1 hour and 30 minutes (6:00pm -7:30pm) 2 hours and 30 minutes (Noon-2:30pm) or (3:00pm -5:30pm)
About
Great affordable option for a group that wants to celebrate a special occasion, sight see OC, or have a fun time on the water! Less than 6 people? Check out our custom cruises and pony tours on The Calypso.
The Calico Jack is a 48’ Coast Guard Inspected Custom Chesapeake Headboat offering 1.5 and 2.5 hour private cruises.
The clean and comfortable accommodations are great for parties, such as birthday, anniversary, bachelorette, and bachelor parties.
Food and drink (including alcohol) are permitted, but not supplied or served. We provide a large cooler and ice, free of charge! Decorations are welcome and an 8-foot table is provided for your convenience. Due to the style of the boat you will not be able to get on and off of the boat to swim.
The boat is designed to offer you the most enjoyable experience with bench seating, restroom, and Bluetooth radio: so get your playlist ready!
During or at the end of your charter, you can request to the Captain to stop or drop you off at a local bar/ restaurant. The Calico Jack is a large boat and can stop/ drop off to locations such as Fishtales on 22nd and Sunset Grille in West OC. Unfortunately we cannot take you to Seacrets, or locations north of 32nd St.
The Calico Jack departs from 32nd street bayside, next to Jolly Roger Amusement Park and there is plenty of FREE parking along 32nd street.
Adventure Tips
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.
Local Insights
Wildlife
- Assateague wild ponies
- Ospreys and herons
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.
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Adventure Hotspots in Ocean City
Frequently Asked Questions
Recommended Gear
Sunscreen
Protects your skin from strong UV rays during the daytime cruise.
summer specific
Hat and Sunglasses
Helps shield your face and eyes from the sun's glare on the water.
summer specific
Light Jacket or Windbreaker
Keeps you comfortable against wind and cooler bay temperatures.
spring specific
Reusable Water Bottle
Ensures you stay hydrated throughout the cruise.