Cruising Sailors

of St. Michaels

  Day One


The purpose of the Cruising Sailors of St. Michaels is to have the benefit of sailing in the company of others rather than alone and thus provide added safety and incentive for cruising. A secondary purpose is fun and fellowship.


Cruising Sailors of St. Michaels was launched in 1971 when seven residents met to organize a club dedicated to cruising the Chesapeake Bay and beyond. From the beginning, as many as 46 boats have been members and well over 365 cruises have been conducted to almost every navigable bay, river, and creek on the Chesapeake Bay. There have been more ambitious trips to Philadelphia and New Bern, NC. The group has evolved beyond the traditional sailing season, April though October, to include formal and informal social events throughout the year.


Interested parties must own a sailboat in the immediate vicinity of Talbot County, Maryland, commit to a minimum of two cruises involving at least six nights over two years on their boat, and initially be sponsored by an active CSSM member.  For additional information, please click here to view a membership brochure.

Membership Process

  • Sponsorship by an active CSSM member
  • Complete six (6)nights and two (2) cruises
  • Complete application and liability waiver and forward to sponsor
  • Sponsor endorses and forwards to the Commodore
  • Commodore confers with active members and accepts or rejects the application

Membership Profile

  • Fun, flexible, friendly, fair
  • Willing to captain cruises
  • Willing to hold office
  • Able to lead OR follow
  • Team player
  • Helps/Volunteers on land or sea
  • Strives to improve quality of CSSM
  • Active Cruiser

Contact Us

If you have any questions, please contact us.