Chicago sailing, Detroit sailing, instruction, sailboat lessons, an innovative sailing timeshare program and more.

Acclaimed Approach

Are you entirely new to sailing or powerboating? Has your experience been aboard smaller boats or in different waterways? Do you have skills that simply need refreshing? Pinnacle's acclaimed sail and powerboat courses will have you captaining your fabulous Pinnacle yacht safely and confidently - it's a breeze!

Available to Members in our shared-yacht program and their families and friends, Pinnacle training courses teach essential knowledge and skills so you can enjoy your time on the water like a pro.

If your dream is to charter a yacht in places like the Caribbean, Europe or the South Pacific, Pinnacle instruction is the perfect compliment to your helm-time experience gained as a Pinnacle shared-yacht Member. With both education and big-boat experience, you will qualify to charter a yacht anywhere in the world.

Pinnacle Members may attend training sessions with a spouse, adult child or friend. This fosters joint learning and confidence, and sharing the experience with another close to you is great fun. The training is comprehensive and the tenor is friendly, relaxed and supportive.

Hands-on instruction courses are scheduled prior-to or early in the season, on the yacht you will be captaining in the Pinnacle Fleet; not the smaller, older training boats typically used by most schools.

Pinnacle instructors are highly seasoned mariners who are also great teachers. Their love and respect for the sea is reflected in their passion for teaching others the same.

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"I want to thank you for a great sailing season. I know I have said this before, but you really run a great company and I just appreciate the great work you and your team do to make sailing in the city such an enjoyable and manageable process. Randy introduced me to [Captain] Phil this summer and he has been a great resource for expanding my sailing skills and knowledge."

G. H.
Financial Services Executive
Captain, Heartbreaker

Chicago sailing, Detroit sailing, instruction, sailboat lessons, an innovative sailing timeshare program and more. Sailboat instruction, lessons, sailboat timeshare program, Detroit & Chicago sailing.