Roster of Sailboats

Pinnacle’s Luxurious Sail Fleet

Pinnacle Yachts provides its Members with the highest quality yachts so they can enjoy Chicago sailing all season long. The Pinnacle approach to sailing eliminates the difficulties of buying a boat or renting a boat for a few short hours — instead we offer a lease-share program that affords Members all the benefits of owning a yacht, without the hassle.

Pinnacle’s sailing fleet consists of the finest Jeanneau sailboats hailing from Chicago’s most sought-after harbors. Each yacht in our sailboat share program is equipped and finished to the highest standards, with sleek hulls and topsides, richly appointed interiors, and advanced instrumentation. They are performance-cruising yachts that move smoothly and swiftly across the water. View our comprehensive list of sailboats offered through our fractional timeshare program.

Pricing and Availability
Belmont HarborView Harbor
Clair de LuneSail2017Jeanneau 419Details
IrisSail2021Jeanneau 410Details
VirtuosoSail2015Jeanneau 409Details
AlexaSail2021Jeanneau Sun Odyssey 389Details
StormySail2005Jeanneau Sun Odyssey 37Details
Dusable HarborView Harbor
Forever YoungSail2020Jeanneau 410Details
AreteSail2019Jeanneau 419Details
Glory DaysSail2019Jeanneau 419Details
SeaglassSail2018Jeanneau 440Details
FearlessSail2015Jeanneau 439Details
My WaySail2008Jeanneau Deck Salon 45Details
Cherish the DaySail2008Jeanneau 40.3Details
Wind Cries MarySail2015Jeanneau 409Details
Burnham HarborView Harbor
American GirlSail2019Jeanneau 419Details

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“I am really looking forward to the upcoming boating season. While I won’t be with Pinnacle this season I am excited about Pinnacle’s move to 31st Street. I never would have had the chance to buy my own large boat without the experience I gained on your boat last year. If I was still a working stiff I would be back with you guys in a heartbeat. Your operation is top notch. The training and response to maintenance issues were superb. I have been talking up your program and while I didn’t send you any customers this year I am sure I will in the future. Again thanks for the great experience, if I can do anything to assist you let me know.”

Retired Financial Professional
Former Captain, Independence Day