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Do you want to sail beyond the Key Bridge and explore the Chesapeake? Or do you dream about a sailing vacation in the Caribbean? You are not alone.

Many Downtown Sailing Center (DSC) members eventually want to learn to sail larger boats. The DSC Cruising Program provides recreational and educational sailing opportunities on our fleet of cruising sailboats. DSC Cruising Skippers and Cruising Crew enjoy learning, daysailing, and even taking trips to locales like Rock Hall and Herrington Harbor.

By participating in the DSC Cruising Program, you can:

  • learn the necessary knowledge and skills to safely operate the DSC the vessels in the cruising fleet
  • volunteer for DSC cruising events and the various community programs of the DSC
  • learn how to maintain and repair cruising sailboats with internal engines and electrical systems
  • take courses, participate in on-the-water trainings, and attend lectures on topics of interest to cruisers
  • accumulate hours underway to build a successful sailing resume to graduate from cruising crew to cruising skipper

Cruising skippers are DSC members who have the demonstrated knowledge, skills, and experience to sail the cruising sailboats while maintaining the value and integrity of the vessel and safety of the crew. Cruising Skipper Candidates are evaluated on successful completion of the application process as outlined in the cruising skipper requirements. 

Click on the links below to learn more. 

Cruising Council Members and Boat Managers

Cruising Skipper Requirements

Cruising Skipper Prerequisites

Cruising Skipper Candidate Program

Boat Orientation Videos

Cruising Education Materials

Seminar Handouts and Technical Information

Email for more information about the DSC Cruising Program.


Cruising Member Sails

Cruising Skippers and Crew take out the cruising boats on Sunday and Wednesday Member sails. Cruising Crew receive priority but all are welcome when space is available. The event runs from noon till 4:00 PM.

Sunday Funday Races

Cruisers race on some Sundays instead of the member sail event. The event starts at 12:00 and ends at 4:00 PM. We race to Curtis Bay and back. Because some boats are faster than others, this is setup as a PHRF race and finish times are corrected at the finish. Skippers and crew are assigned to the boats based on the experience level, and we rotate boats so that people can race on different boats. This is a fun race and the rules are simpler than the ISAF rules.

Full Moon Sails

Scheduled to coincide with the full moon, these popular events are an opportunity to do some night sailing. Full moon sails leave the docks at approximately 7:30 PM and may return as late as 11:00 PM. Crews will be contacted by a cruising skipper as to boat assignment and time to meet on the dock for departure (times vary based on time of sunset).  Open only to cruising-level crew and skippers.  One week advanced registration required.

Overnight, Weekend and Raft-up Cruises

The highlight of the cruising season, these popular events are a great opportunity to get some real cruising experience.  Scheduled approximately one per month throughout the season, these events are overnight cruises to a predetermined destination on the Chesapeake Bay.  The raft-up cruises involve the DSC cruisers and other privately-owned boats for a rendezvous either anchoring or docking together.  Crews will be contacted by the event coordinator as to boat assignments and other pertinent information prior to departure.  Open only to cruising-level crew and skippers. 

Newbie Cruises

Newbie Overnight Cruises are offered for any DSC member who is interested in learning more about the cruising program. Crews will be contacted by the event coordinator as to boat assignments and other pertinent information.  Open to DSC members and cruising-level members free of charge.  

Work Parties

Work parties are held on usually on the weekends and sometimes during the week in March and April and early November. You can check with individual boat managers to see if there are projects you can work on other times during the week if you can't make it to these scheduled work parties.

Cruising Skipper Development

These educational events are structured to provide informal and free training opportunities for the cruising crew members interested in becoming a DSC skipper.  These day long events, led by volunteer cruising skippers, emphasize basic skills and safety, and will allow participants to practice and improve their knowledge and skills, which are essential for an enjoyable and safe sailing experience.


  • DSC cruising skippers have the necessary sailing resume and skill level to sail the DSC cruising vessels.
  • DSC cruising skippers are expected to regularly volunteer as skippers for the scheduled cruising events, accessible-sailing program and for fleet-maintenance work parties throughout the year.

Email for more information about the cruising program.


The Downtown Sailing Center

Est 1994
1425 Key Highway, Suite 110, Baltimore, MD 21230
(410) 727-0722 •

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