Sailing Lessons

Sailing Course

Pinnacle’s sailing lessons were created for Pinnacle members and their crew, with limited or no sailing experience, that seek to build the skills needed to handle their Pinnacle yacht safely and confidently.


Pinnacle believes that the best learning occurs by doing. With this in mind, this course is conducted on your Pinnacle yacht or an identical yacht in the Pinnacle fleet; and is structured to provide much practical, hands-on experience. The sail lessons cover:

  • Yacht equipment and uses
  • Operating principles and techniques
  • Safety procedures
  • Navigation rules
  • Docking and mooring
  • Anchoring
  • Night piloting


The course is comprised of three lessons which are conducted on the water, plus an online pre-requisite lesson, an in-class seminar, and an online exam.

On-the-water lessons occur early in the season, prior to your first personal use of your yacht and do not take away from your allotment of time. The online materials are prerecorded and can be viewed anytime after the lesson series has begun from your computer or mobile device.

Most Chicago sailing lessons happen on weekday evenings, and on weekend days and evenings, such that they do no disrupt typical business hours. An online course catalog is published in the Spring which presents multiple course schedule options to fit your particular needs.


$800 per person for the entire series.

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“With multiple interests, the timeshare program — with it’s flexible scheduling, excellent equipment and no maintenance — fulfills my passion for sailing.”

CEO, Electronic Component Company
Captain, Moon Dance