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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 Education Program provides educational sailing opportunities on our fleet of cruising sailboats. Members can work on skills together by taking classes, mentoring each other, and sailing together.

The DSC Cruising Education Program provides opportunities to:

  • learn the necessary knowledge and skills to safely operate the DSC the vessels in the cruising fleet
  • volunteer for DSC 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, share skills through mentorship, and attend lectures on topics of interest to cruisers
  • accumulate the skills necessary to pass a cruising skipper checkout
  • obtain US Sailing Basic Cruising and/or US Sailing Bareboat Cruising certification

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 via a comprehensive cruising skipper checkout process.

Cruising Resources are available HERE, including documentation on becoming a skipper, vessel-specific resources, and more.

CRUISING Membership upgrade

Cruising Education Program Description

The Cruising Education Program is described in full here. This document includes details about membership upgrades, cruising skipper checkouts, plans for the DSC cruising fleet, and classes and instructors. 


Volunteering is a critical part of being a DSC member. All members are encouraged to volunteer as specified on the Volunteer page.

DSC cruising members are specifically encouraged to help with the following tasks:

  • Maintain the cruising boats by participating on the Boat Manager Committee or on the Maintenance Committee.
  • Cruising skippers are needed as skippers for Member Sails, Women on the Water, Full Moon Sails, and Community Outreach Programming.
  • Cruising skippers may also earn volunteer hours by mentoring others working towards a Cruising Skipper checkout.

    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 •