Chronic Sailing

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We are a sailing school and charter boat company based in Annapolis. We offer daysails, sunset cruises and overnight stays on our fleet of luxury sailboats. Enjoy an outing on the beautiful Chesapeake aboard one of our catamaran or monohull options.

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Location

7082 Bembe Beach Road

Suite 204

Annapolis MD 21403

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Central Maryland

	Cruises Deals Url https://www.chronicsailing.com/charters/ Equipment Rentals Available Family-Friendly Free Parking Video Url https://www.youtube.com/watch?v=2a0T3l9y9Eg

May 01, 2026

Peyton C

Private Instruction

Wow! We had an amazing experience working through Chronic Sailing and with our instructor Harish! We requested some instruction to improve our docking skills on our new sailboat and Harish delivered...

June 30, 2025

S6840ALreneeh

Perfect evening

Perfect evening of cruising the Chesapeake! Everything was smooth sailing. Great way to spend time with friends and colleagues.

May 16, 2025

Gary M

Great weekend of sailing lessons and fun.

We had the pleasure of taking 2 days of family sailing lessons with Captain Shawn. I’ve owned a 41’ sailboat for eight years and was looking for someone to help my family feel more confident sailing...

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