The yacht OCEAN, Chicago's flagship and largest racing sailboat, was donated to California State University Maritime Academy in Southern California in November 2018. (Press release here)


The Pinnacle Foundation is excited to  welcome VINCITORE, a Reichel Plugh 52', to Chicago. VINCITORE will take OCEAN's place as one of the Pinnacle Foundation's fundraising opportunities.


While sailing the magnificent VINCITORE you will witness a spectacular array of aircraft as the famous Chicago Air & Water Show releases its awesome might.  Join the fortunate few who will enjoy this great event from the water aboard this magnificent yacht. 


We will sail fast but conservatively, and anchor near the show epicenter if conditions permit.  You may help sail the yacht, if you wish, and experience is not required.


A delicious catered lunch will be provided.  The yacht sails dry meaning adult beverages are not allowed.  Your donation of $300 reserves a seat for the entire day aboard VINCITORE for this once-in-a-lifetime experience. 

Air Show Aboard the Yacht VINCITORE –

The Sleekest Turbo Yacht to Sail Chicago's Lakefront

The Chicago Regatta –

Exhilarating Yachting Events & Rocking Party



The Pinnacle Foundation has passed the Chicago Regatta on to the Chicago Yacht Club, who has generously agreed to organize and manage the event. 


The Chicago Regatta is collection of phenomenal yachting events and parties to benefit the great families and kids of the Pinnacle Foundation. 


Participate in an exhilarating race across Chicago’s fabulous lakefront.  Tour waterfront landmarks from a spectacular yacht.  Ride along on a world-class racing cat.  Join the post-race party at the renowned Chicago Yacht Club. The Chicago Regatta has something for everyone, and all for a great  cause. 


Not a boat owner?  No problem.  We have arranged boats of all sizes and types for you to enjoy.  You may charter and entire yacht or just a few seats.  USCG Capatins are available to run the boat as well.  So sit back and relax; we've got you covered.





The Pinnacle Cup – Corporate Yacht Race Challenge



Aboard a fleet of magnificent Jeanneau sailing yachts, teams from your company race in pursuit of the coveted Pinnacle Cup.  Team members rotate through the positions of helmsman, mainsail trimmer and jib trimmer under the guidance of a skilled USCG Licensed Captain, so prior experience is not required. 


The event begins with the race briefing over a fabulous lunch at the Chicago Yacht Club.  Steeped in nautical tradition, the club sets the perfect tenor for the race.  The fleet then departs and teams practice.  Yachts converge to the start area and jockey for best position.  Adrenaline fills the air as the gun is anticipated.  The race commences and the yachts round four marks on reaching legs.  The boats and their crew endeavor for the glory of being first to finish, as photographs record this epic competition.  Afterwards, the fleet returns to the Chicago Yacht Club for drinks, camaraderie and presentation of the Pinnacle Cup. 


Your donation of $295 per seat covers your crew of up to six people and includes USCG Captain fees, the yacht, yacht club facilities.  This price may be adjusted based on group size.

Blues Benefit Concerts with Sons of Chicago



Shake your groove thing Baby to blues and soul masters, the Sons of Chicago, in concert at one of the many music venues in Chicago.

The Sons of Chicago is a band made up of Chicago's best professional Blues, R&B and Soul players, coming together to form a dynamic collective, spreading their home grown message of neighborly love.


The Pinnacle Foundation uses proceeds from these benefit concerts to raise money for our many worthy causes.


Custom On-The-Water Events That You Design



Thinking about an event for you group that is truly unique? With a fleet of thirty sail and power yachts from 37 to 86 feet at five marinas in Chicago, we can accommodate groups of up to 100 people.  Please contact us to discuss your ideas.

 Copyright Pinnacle Foundation, NFP