Employment Opportunities

Join Our Team in Annapolis and Baltimore

Watermark employees
Colonial tour guide
Watermark employees

Watermark has built a solid reputation for delivering products in a unique and authentic way thanks to the help of our skilled event planners, tour guides, captains, and crew.  Our organization seeks people who naturally generate warmth, friendliness, and kindness in addition to possessing the expert skills required to fill the positions below. 

Watermark has several seasonal and part-time positions throughout the year in both Annapolis and Baltimore.  They include:

To apply for one of the part-time positions noted above, complete this application (PDF). Please submit completed application for Land positions to heather@watermarkjourney.com and for Water positions to ginny@watermarkjourney.com.


Full-Time Positions:

  • Director of the Fleet: Learn more about this opportunity and how to apply here. (opens as PDF)
  • Full-Time Captain: Watermark is accepting applications for a full-time Captain. Great opportunity. Experience necessary. Learn more about this opportunity here. (opens as PDF)

  • If you are interested in learning more about becoming a part of the Watermark team, please contact us at info@watermarkjourney.com.

    Completed applications may also be mailed to:
    P.O. Box 3350
    Annapolis, MD 21403