Sailing is rich with business parallels.

Sailing is an activity that succeeds with teamwork, communication, quick thinking, problem solving, and solid leadership. Sailing parallels the environment at work - constant changes and ‘unknowns’ are thrown at a group who must quickly adapt to deal and deal with the situation at hand. Like a sailing crew, your team is a group of people with a common goal. They depend on each other to produce successful outcomes, communicating constantly and informally to “get it done.”


Sailing is inclusive.

Think about it, golf isn’t much fun if you’re not a golfer. But with sailing, non sailors can enjoy both the voyage and participating as a crew member. No sailing experience is necessary. Our professional facilitators are experts at teaching sailing skills while keeping everyone safe.


Sailing is fun.

It’s hard not to have a big smile on your face while enjoying a good day on the water, marveling at the Chicago skyline with a cool breeze on your face. Sun, wind, motion, scenery - an absolute thrill!

Group Racing

Chicago Sailing’s group regattas offer a creative team building event to inspire your team for tomorrow’s challenges. Our professional facilitators will teach the basics of sailing to your group, then guide them through a series of fast-paced races that replicate the ever-changing challenges of today’s workplace. After each race teams are given an opportunity to refine their plan, improve their communication, and identify the best positions on the boat for each team member.


Number of hours:  3 or 4 hours


Scheduling Options:

3-Hour or 4-Hour Format; starts anytime between 8 am to 4 pm.


Cost:  3-Hour Format: $150/person

            4-Hour Format: $175/person


Group Size: 6 - 50


Vessels: J/22's

Educational Sail

If your team prefers to spend a more leisurely day on the water, you can forgo the races with an educational sail. In this group lesson, your team will learn the fundamentals of sailing, and improve their skills in communicating and working together toward a common goal. Without the element of competition, your teams can focus on supporting each other in a hands on sailing experience.



Number of hours:  3 or 4 hours


Scheduling Options:

3-Hour or 4-Hour Format; starts anytime between 8 am to 4 pm.


Cost: 3-Hour Format: $110/person

            4-Hour Format: $140/person


Group Size:  6 - 50


Vessels: Various Vessels

Interested? Let chat.
Or Call Us: 773-871-SAIL x3



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