Since 2001 Olson’s Classic Yachts has been making the sailing lifestyle accessible for Chicago area boaters through our fractional leasing operation. Pioneers of the fractional leasing concept, we have spent the past sixteen seasons honing our operation to best serve the needs of Chicago area sailors. With 10 boats ranging from 27 to 42 ft., we have a boat for every sailor, experience level and a plan for every budget (season-long packages range from $1,850 to $4,850).
New for 2017! We've added a tenth boat. Dame, a Catalina 27 MkII, will be moored on a 35' slip at Chicago's Jackson Park Outer Harbor. A legacy jewel from the 1893 World's Fair, Jackson offers the intimacy of a small, picturesque sailboat harbor. The harbor is Close to fantastic restaurant scene in Hyde Park and the Museum of Science and Industry is a stone throw away from the harbor. A unique aspect of Jackson Park is the camaraderie and facilities that come with a yacht club membership at the Jackson Park Yacht Club. JPYC is a fantastic group of sailors with a family oriented atmosphere with plenty of opportunities such as social events, racing programs and youth sailing program. Together, the incredible value for slip, boat and yacht club membership makes this one of Chicago's best kept secrets.
​In Monroe Harbor it became evident that additional capacity was needed in the easy to sail, well equipped 30-33ft. range of boats. To meet this need, we're expanding our Monroe fleet to eight boats with the addition of Playful Tiger, our Morgan 321. She is a solid boat with great sailing characteristics and a well-appointed cabin. She is an intuitive boat to sail and is as sturdy a boat as you find in her class. If you are interested in leasing her act fast as we are expecting she will fill up quickly. Playful Tiger is a great boat for someone just getting into sailing who wants an easy handling boat with simple controls and good all-around sailing performance.
In a bitter-sweet move we have retired the beloved Whirlaway from the system. Whirlaway, a Catalina 27, was our very first lease share boat back in 2001 and she served faithfully for 16 seasons. In her place we have added a Little Darlin’ and the afore mentioned Dame, both Catalina 27 MK2s. These are the updated versions of the original C27 and are well outfitted with self-tailing winches, wheel steering and many of the appointments of a cruising boat. Little Darlin’ will be taking the place of Whirlaway in Monroe Harbor and Dame will be our first boat in Jackson Park Outer Harbor which is Chicago’s most Quaint and peaceful harbors.