Overnight Cruise to Annapolis

Set sail for an unforgettable overnight adventure to Annapolis, MD! We’ll cruise across the Chesapeake Bay, enjoying scenic views and time on the water before arriving in the historic sailing capital of the U.S. Once docked, you’ll have time to explore the charming waterfront, unwind with a happy hour drink, and enjoy dinner at one of Annapolis’ many local restaurants. After a relaxing evening, we’ll spend the night aboard and wake up to a peaceful morning on the water before sailing back. The trip is a perfect blend of adventure, relaxation, and classic Chesapeake sailing.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Dockside Meetup Time 

0700

Event End Time

1400 (+1)

Waivers Required

If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

Have Questions?

If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 10 PM on the day before the event.