Chronic Sailing

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.

Hours See website for hours.

Location

7082 Bembe Beach Road

Suite 204

AnnapolisMD21403

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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 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...

December 23, 2024

Adam G

Outstanding Experience With Chronic Sailing

Our family is spread across the country without young children or grandchildren, so we opted to spend Thanksgiving on the Cheespeak bay. We bareboat chartered "Slowdown" (a Dufour 430) from Wed...

September 01, 2024

April C

Perfect way to Celebrate!

When visiting Annapolis, you have to charter a boat with Chronic Sailing. Captain Shawn and his crew provide such an amazing experience, and the boats are beautiful! My friends threw me a 40th...

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