Upper Chesapeake Boat School

Upper Chesapeake Boat School ⚓️Here to help boaters feel more comfortable and confident at the helm!
🪢Group classes and private lessons

05/21/2026

🚤 Nothing beats hands-on training! Learn to dock the boat like a pro!🏆
Single Engine or Twin Engines 🚤🚤
🛥️ Your boat or one of ours!
We got you! 💪 Link in bio 🔗

☀️ Gorgeous day on the water with Captain Lauren and student Kim! From docking practice in shifting winds to navigating ...
05/18/2026

☀️ Gorgeous day on the water with Captain Lauren and student Kim! From docking practice in shifting winds to navigating the Sassafras using channel markers, this lesson was packed with real on the water experience. Once the wind settled, Kim also got to practice anchoring and enjoy some beautiful time out on the river. 🌊

Every lesson is hands-on, confidence building and tailored to help students feel more comfortable behind the helm in real boating conditions. Our captains are here to help you learn while still having fun out on the water!

📲 Check out our upcoming classes before they FILL, Link in bio or 📞Call 410-205-6105

⭐️Private Lesson Spotlight⭐️Captain Lauren’s lesson with Robyn and Donald this past weekend went great. Even with windy ...
05/13/2026

⭐️Private Lesson Spotlight⭐️

Captain Lauren’s lesson with Robyn and Donald this past weekend went great. Even with windy conditions, these first time boaters crushed it!

During their lesson, they practiced docking alongside, backing into a slip, anchoring, and open water navigation — gaining real hands on experience out on the water.

We’re excited to keep the momentum going this summer with both private and group lessons available⚓️ Ready to get out on the water? Contact us to book today! 410-205-6105

🚤 First class of the season = success!We dodged passing showers without feeling a single drop while Sue, John, Gerry, an...
05/13/2026

🚤 First class of the season = success!

We dodged passing showers without feeling a single drop while Sue, John, Gerry, and Victoria took on shifting winds during close quarter maneuvering practice💨🌊.

The highlight? Gerry expertly brought the boat back onto the dock after spinning around in a 2 knot current — not an easy task👏🏼

Huge congratulations to everyone on a job well done and an amazing start to the season. Here’s to more confidence, learning, and time on the water ahead!
‼️Check out our May Classes — Link in our bio.

Today we celebrate the moms at the helm of every great adventure. ⚓️
Happy Mother’s Day from the Upper Chesapeake Boat S...
05/10/2026

Today we celebrate the moms at the helm of every great adventure. ⚓️
Happy Mother’s Day from the Upper Chesapeake Boat School family to yours. Wishing you a beautiful day on and off the water 💙

The UCBS crew has been putting in miles this spring⚓️From Florida to Maryland and all along the East Coast, our captains...
05/06/2026

The UCBS crew has been putting in miles this spring⚓️

From Florida to Maryland and all along the East Coast, our captains have been busy delivering boats and helping clients get where they need to go — safely and stress-free👏🏼

⭐️Captain Lauren: 1,041 nautical miles (Lighthouse Point,FL —> Annapolis, MD)
⭐️Captain Alan & Mate Captain Slater: 143 nautical miles (Baltimore—> Ocean City, MD)

Boat deliveries are just one of the many ways we support our students on the water — alongside our hands-on lessons designed to build real confidence behind the helm

Big journeys, experienced captains, and a season just getting started.

Spring lessons are in full swing⚓️Caitlin spent the day mastering open water navigation and dialing in docking and close...
05/02/2026

Spring lessons are in full swing⚓️

Caitlin spent the day mastering open water navigation and dialing in docking and close-quarter maneuvering on their new boat🚤

We also covered the essentials — navigation, VHF radio, and reading the weather, so she’s ready to get out on the Bay with confidence!

Nothing better than turning new boat excitement into real skills👏🏼
‼️Spots are filling — secure your lesson for the season.
Who are you bringing out on the water? Tag them below 🌊

And just like that…we’re back🚤Our Single engine training boat — “Seas Get Degrees” is officially in the water and ready ...
04/24/2026

And just like that…we’re back🚤
Our Single engine training boat — “Seas Get Degrees” is officially in the water and ready for another season of hands-on training out on the Chesapeake!

⭐️Spots are filling fast for the season — join us & find your confidence at the helm⭐️
📞410-205-6105

⚓️Been working on something fun…New UCBS hoodies are coming — made for comfort on and off the boat🌊⭐️ Moderate crop (rig...
03/30/2026

⚓️Been working on something fun…
New UCBS hoodies are coming — made for comfort on and off the boat🌊

⭐️ Moderate crop (right at the waist) & standard fit options available.
⭐️ Discounts on all preorders.

Message me your size & fit if you’re interested! 👀

☀️🌴

BIG NEWS 🚤✨You asked… and we DELIVERED!! 🙌Due to high demand, we’ve added TWO Twin Engine classes this May 🔥If you’ve be...
03/21/2026

BIG NEWS 🚤✨
You asked… and we DELIVERED!! 🙌
Due to high demand, we’ve added TWO Twin Engine classes this May 🔥

If you’ve been waiting to level up your boating skills… this is your sign 👀
👉 Sign up now before spots are gone!
www.chesapeakeboatschool.com

Address

Chesapeake City, MD
21915

Telephone

+13026905762

Website

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