Upper Chesapeake Boat School

09/02/2026

Looking forward to this awesome event!
🚤We’ll be there with new merch! Be sure to stop by our booth!
🦀Great way to support some great Chesapeake Bay Captains!
Who else is coming?! 9/26/26 🗓️ MARK YOUR CALENDARS! 📍Chesapeake City, MD

08/29/2026

2026 Sassafras River Days and docking contest was a success! 🌊⚓️

Thanks to everyone who stopped by our booth and showed off their skills in the docking contest. 🚤🏆 It was a great day on the water filled with good times and plenty of boating fun!

Interested in building your boating confidence? Click the link in bio or give us a call! (410) 205-6105

08/20/2026

Welcome to the crew, Captain Danny! ⚓️

With years of experience on the water, Danny brings a lot of knowledge to the Upper Chesapeake Boat School. Read Danny’s full bio and why he makes a great addition to the crew on our website! 🛥️

08/16/2026

POV: you finally stopped saying “I’ll take a boat lesson someday” 🚤🌊

Whether you’re a first-time boater or just looking to feel more confident behind the wheel, a little hands-on experience can make all the difference. Learn how to safely navigate, dock, maneuver, and handle the boat with confidence so you can spend less time watching from the passenger seat and more time taking the helm.

Your next day on the water could look a little different. ⚓️

Ready to take the wheel? Book your lesson with Upper Chesapeake Boat School and start building your confidence on the water.

08/11/2026

⚓️🌊 A birthday gift that turned into a day they’ll definitely remember! 🎂

For Aakanksha’s birthday, Monarch gifted her a private lesson aboard Seas Get Degrees! They had an incredible time out on the water, working on close-quarters maneuvering, pulling up to a T-head, and getting on plane.

They both did a fantastic job and loved every minute of it! By the end of the lesson, they were already talking about booking another one and looking forward to getting back on the water together. 🚤

08/01/2026

Student Spotlight! ⚓️

Rob had a great day aboard his Crownline 264 in Havre de Grace, focusing on the fundamentals of close-quarters maneuvering, slow-speed boat control, docking… and then even more docking! 🛟 The wind definitely added to the challenge, but he stayed focused, kept practicing, and finished strong. I think Neutral may have become his new best friend. Way to go, Rob! 🛥️

07/29/2026

Hear directly from Captain Lauren about what makes Upper Chesapeake Boat School such a unique place to learn! 🛟

From personalized, hands-on instruction to real-world boating scenarios, every class is designed to help students build confidence! Whether you’re brand new to boating or looking to sharpen your skills, Upper Chesapeake Boat School is passionate about creating a welcoming environment where you can learn at your own pace and feel comfortable asking questions.

Ready to start your boating journey? We’d love to have you on board! ⚓🚤

07/22/2026

Derick, Zina, and Zamari spent the day aboard our twin-engine training boat, building confidence and sharpening their boating skills. 🛟

During the lesson, they practiced twin-engine operation, marina maneuvering, and precision docking using engine power to pivot the boat, without touching the wheel while docking. They also headed into open water to learn how to properly use trim tabs for a smoother, more efficient ride. 🛥️

By the end of the day, they all successfully docked the boat multiple times, putting their new skills into practice.

Great work, Derick, Zina, and Zamari! 👏⚓

07/19/2026

🛥️🛟⚓️😎🎓

What a great Experience I had with Captain Alan Roe with Upper Chesapeake Boat School! I had my first Twin Engine lesson yesterday and it was awesome. Captain Roe’s expert instruction made it possible for me to reach my objectives I set for myself! Can’t wait for another day on the water to solidify what I just learned! Five Stars for these guys!!⭐️⭐️⭐️⭐️⭐️

07/17/2026

Thank you to everyone who came out and made this year’s Antique Boat Show such an awesome event! ⚓🚤

As a proud sponsor, we were honored to be part of a day celebrating classic boats, boating history, and the incredible community that shares a passion for life on the water.

Thank you to the organizers, exhibitors, volunteers, and everyone who stopped by. We enjoyed meeting so many fellow boating enthusiasts and look forward to seeing you in the future!