During the 2012 season my wife and I had a 'time share' through Pinnacle Yachts. Our boat was a Jeanneau 40.9 out of Belmont Harbor. The 'standard' share is 11 weekend and 16 weekday timeslots, where a timeslot is from 9:00 am - 5:00 pm or 5:00 pm - 9:00 am, at a lease cost of about $7,500 plus a refundable membership fee (deposit) of $1500. You can buy more timeslots ("super-share") or fewer ("partial share").
New Pinnacle members need to participate in check-out sessions - I think there were three, and they were worthwhile in terms of building familiarity with sailing on Lake Michigan as well as the protocols for using the boat. There's an exam at the end - easily passed if you pay attention during the check-out sessions.
Pinnacle uses a clever and sophisticated scheduling system. We were able to bundle timeslots into 24 and 36 hour periods by exchanging with other captains. The website promises week-long trips, but in 2012 that option was not available to first season participants. There are some restrictions on when and where you sail, but they are driven largely by common sense and safety considerations. Our purpose was day-sailing with friends, and we never felt constrained.
It's truly a walk-on, walk-off proposition. On a sailing day, we would pull into the harbor, park, walk out to the boat, and make ready to sail. The Jeanneau was in excellent condition, and Pinnacle's maintenance was first rate. Once a week they fill the diesel and water tanks, and empty the holding tank. We once noticed a 4" tear in the foresail, reported it, and three days later when we went out again there was a completely new sail in its place. The other captains sharing the boat left it spotless (as did we).
If we lived in Chicago we would be back with Pinnacle. It was a terrific experience; Gary Feracotta, the owner, is a standup guy who gets it right and gives back to the community.
Things you would want to consider, however:
The Pinnacle package is ideal for people who have flexible work schedules. If you work a standard 9-5 weekday job, your weekday sails will be in the 5:00 pm - 9:00 am slot. It will be harder to 'bundle' timeslots. Evening/night sailing in Chicago is gorgeous, with two exceptions: stay away from the Navy Pier area during fireworks nights - lots of drunk idiots zooming around without lights. Same is true for the 'Holding Pen' off Oak Street Beach.
Pinnacle's boats all have furling mains and jibs. If you want to hank-on sails before leaving the harbor and flake them on your return, look elsewhere. We were fine with this set-up because it kept us and our friends off the deck in rough weather - Lake Michigan often has 4' or so box waves that make for a bouncy ride.
You'll need a regular crew (one person) to pass the check-out session. Single-handing is prohibited by the Pinnacle contract, and you don't want to be driving a 37' - 42' foot boat in and out of the Chicago harbors by yourself. Also, my wife and I had intentions similar to yours: taking or friends out sailing. We were surprised how often our friends found reasons to stay on shore. There were many days or evenings when it was just the two of us, and we were glad we could count on each other. By the end of the season we had good routines for leaving and returning to the slip without drama - and we're old, fat and clumsy.
If my memory is correct, Pinnacle prohibits boats from going out under a small craft advisory. That wasn't a problem for us - we were not eager to be out in 30 knot winds with eight feet waves coming out of the North! If the weather sucks during your timeslot, too bad. But there are options for last minute scheduling if the boat becomes available because another Captain changes plans.
$7500 or so isn't pocket change. It's certainly cheaper than owning a 40' boat and keeping it in a Chicago marina, but probably is more expensive than Sailtime or Sail Chicago. It really is a first-class, premium experience.
Pinnacle can be found at
Yacht Leasing and Fractional Charter Boat Rental of Sea Ray Powerboats and Jeanneau Sailboats in Chicago, Annapolis, Miami
