Join Our Team of Industry Experts

Waypoints Yacht Charters is rapidly growing and we are looking to add new talented professionals to our team. Our company is dedicated to elevating the charter experience for our yacht owners, charter guests, and our employees. We work alongside one another with enthusiasm, excitement, and commitment while serving our guests and providing the best experience possible.

Whether you’re a charter-industry veteran or you have always wanted to be a part of the industry, this is your opportunity to build your career with our experienced team of industry professionals at our bases in Annapolis, MD, St. Petersburg, FL, USVI, and BVI.

Join our crew and help us bring the fun back to the charter industry! Email your resume and cover letter to

Current Job Openings

Charter Sales Manager

As a Charter Sales Manager, you will be responsible for selling yacht charter vacations to our clients throughout the U.S. and the Caribbean. We are looking for a motivated, flexible, team player with industry knowledge. Your leads will come via telephone and email. You will be responsible for working the lead through its life cycle (customer service follow-up and after-sales support/communications).

Waypoints Yacht Charters has 4 bases (Annapolis, St Petersburg, British Virgin Islands, and the U.S. Virgin Islands – St Thomas). We are a small but highly functioning team. The only way to ensure success is to work together. We value experience and insights and will be flexible for change if needed. We are a new yacht charter sales company setting the stage for being one of the top charter companies in the world.

Our industry is very seasonal and in the peak months, can be intense, however, we are a team and will work together to provide a work-life balance.

This job does require some weekend work. As stated above, we ask for flexibility from you, but rest assured, we are flexible and will work with you as well.


  • Education level – bachelor’s degree (preferred, but not required)
  • Previous experience is a plus in yacht charter sales and/or travel and vacation planning.
  • Knowledge of world geography.
  • 2+ years of sales/customer service experience.
  • Exceptional communicator, both written and verbal. Presentation skills are a plus.
  • Comfortable with MS Office, CRM & online reservations systems.
  • Must be available for evening & weekend shifts.
  • Ability to travel when needed.
  • Fluent in speaking/writing Spanish is a huge plus.


This is a salaried position based on a 40-hour work week, plus a sales incentive.


To be considered for this role, please email your resume and cover letter to

Charter Experience Specialist

Waypoints Yacht Charters is looking for a sales-motivated Charter Experience Specialist to add to the team! Waypoints is a boutique luxury charter company offering sailing and powerboat charters in Annapolis, MD, St. Pete, Florida, The Bahamas, the BVI, and USVI.

As a Charter Experience Specialist, you will be working with the sales team to book charters, smash monthly targets, and elevate the overall experience for our charter guests. We are looking for outgoing, sales and money-driven candidates with a “can-do” attitude to join our team. 

Basic computer and email knowledge is a must. We are willing to train the right candidate about our product. Job includes travel to Yacht shows and of course, yacht charter opportunities! Weekend availability required, with a flexible work week schedule. We are team-oriented and we take pride in our jobs in offering fantastic charters for our guests’ vacations.

Job Type: Full-time

Location: Annapolis, MD 

Pay: Salary plus commission


  • Dental Insurance
  • Flexible schedule
  • Health insurance
  • Paid time off

Weekly day range:

  • Monday to Friday
  • Weekends as needed

Work setting: Flexible 


  • Sales: 2 years (Required)
  • Customer Service: 2 years (Preferred)


To be considered for this role, please email your resume and cover letter to 

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