Chesapeake Boating Club
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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!
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!
12/18/2025
Start your New Year on the water with us!
11/25/2025
⚓ Stay connected with J World Annapolis! Get exclusive flotilla updates & sailing adventures straight to your phone. 📲 Sign up for SMS today and never miss the voyage!
Sign up to stay in touch with JWorld Annapolis You agree to receive recurring automated promotional text messages, including cart reminders, from JWorld Annapolis: Consent is not a condition of purchase. Reply 'HELP' for help or 'STOP' to cancel. Message and data rates may apply. View Terms & Privacy.
10/30/2025
Save big on your sailing adventure before October 31! Don’t let this offer sail away!
10/16/2025
🍂 You know what they say… it’s not over till it’s over! ⛵️
Fall is one of the best times to get out on the Bay — crisp air, gorgeous foliage, and smooth sailing. Why pack away summer when you can boat right into the season of color?
Joining the Chesapeake Boating Club means:
✅ All the privilege of boating
❌ None of the hassle of ownership
Just show up, hop on board, and enjoy every moment on the water — from leaf-peeping cruises to sunset sails.
📞 Call today to learn more about membership: 410.280.2040
Because boating season doesn’t end when summer does. 🌊🍁
https://chesapeakeboatingclub.com/
Click here to claim your Sponsored Listing.
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Annapolis, MD
21403
Opening Hours
| Monday | 9am - 5pm |
| Tuesday | 9am - 5pm |
| Wednesday | 9am - 5pm |
| Thursday | 9am - 5pm |
| Friday | 9am - 5pm |
| Saturday | 9am - 5pm |
| Sunday | 9am - 5pm |