Chesapeake Boating Club
Leave us a review: https://forms.gle/Q8W92hczuY9EoqUu6 We offer a variety of boats -- both sail and power -- from 19' to 34'.
Chesapeake Boating Club has been the #1 flexible boat sharing program on the Chesapeake Bay since 1992. We can help you experience the thrill of boating at a fraction of the cost of ownership. Whether you want to go day sailing, cruising for a weekend, or even plan a week-long excursion on the bay with our unique club, the possibilities are endless. Contact us today to learn about our annual memberships!
08/18/2026
J World Annapolis is hosting the official US Sailing Keelboat Instructor Certification Course, and spots are limited. If you’ve been thinking about leveling up your sailing career, now is the time to register.
Already certified or not planning to take it? Share this with a friend or teammate who should be on the water teaching next season.
Let’s fill this course with motivated sailors — register today!
07/16/2026
Adventure Awaits! Learn to sail, level up your skills, and chase the Bay breeze with us.
05/29/2026
It’s a perfect day to go sailing! No boat? No problem — we’ve got you covered. Give us a call at 410-280-2040 and let’s get you out on the water.
03/24/2026
Discover the timeless skill of navigating by the sky and find your place in the universe. — stars over screens.
03/23/2026
⛵ Boaters of Annapolis!
Join us this Wednesday night for a fast, fun, and super useful Annapolis Area Boating Webinar.
Get local insights, pro tips, and a jump‑start on the season — all from home.
Grab your spot and get ready for a stronger season on the water.
SHARK ATTACK at
Our J World Annapolis flotilla had a great time and Captain Tom won the dance contest.
01/12/2026
Math meets the open sea! 🌊📏
Join us January 28, 2026 for a hands‑on Nautical Arithmetic Webinar designed to boost your confidence at the helm. From speed‑time‑distance to course calculations, we’ll make the numbers make sense.
01/09/2026
Wednesday Night Webinar Jan 21: Understanding Marine Weather
01/06/2026
Webinar: Basic Seamanship for Sail & Power boats. Register today!
01/05/2026
~ Winter Webinar Series, Wednesdays at 18:00. Jan 7 - March 25, 2026 Register today!
| Monday | 9am - 5pm |
| Tuesday | 9am - 5pm |
| Wednesday | 9am - 5pm |
| Thursday | 9am - 5pm |
| Friday | 9am - 5pm |
| Saturday | 9am - 5pm |
| Sunday | 9am - 5pm |