Chicago Lake Sailing with Olson's Classic Yachts. SailShareChicago.com
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" Our unsurpassed scheduling flexibility makes Sail Share the best alternative!"
" SailShare: A Better Way to Sail. The concept is simple. We're working to make sailing an activity that people can enjoy as easily as skiing or golf, and without the maintenance hassles and financial commitment of ownership..."

Sail Share an Islander 36 from Chicago's Monroe Harbor

Chicago sailing at its best. Join Today!

Now in our eleventh season making the sailing lifestyle affordable!

Highlights

 
Sensational Sailing Made Affordable by
SailShareSM
SHARED TIME SAILING
-Spend Less – Sail Larger Boat
-Forget about Boatyard Chores
-Forget about Money Sinkholes
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Unmatched Scheduling and  Usage Flexibility

Real scheduling flexibility means choosing the exact dates you want to sail! 

Since 2001 Olson’s Classic Yachts has been making the sailing lifestyle a reality for Chicago area boaters through our leaseshare operation, SailShare Chicago. With six boats, ranging from 27 to 42 ft, in Chicago’s Monroe Harbor, we have a boat for every sailor and a plan for every budget.

We lease seasonal shares on a boat, dividing time throughout Chicago’s May – October sailing season among a small group of captains. Most of our boats have eight shares. Our captains vary in the way they sail, some come out exclusively on weekends, others will take the boat for week long cruises across the lake.

By leasing a share on one of our boats, rather than owning, our captains dramatically reduce their cost of sailing for the season. A full season share on one of our Islanders is less than what it would cost to moor the boat for the summer in Monroe Harbor. Moreover, we handle all maintenance. Rather than spend their Saturdays working on their boat, our captains simply sail.

It’s a great system that appeals to a broad cross-section of sailors. The majority of our captains are experienced sailors who prefer leasesharing to owning. A growing number, however, are relatively new to the sailing world. There are a number of great options to learn to sail in Chicago, but most leave their newly minted sailors wondering “what next” when the lessons are over. We offer lessons on our smaller boats, working with Bob Wagner of SloopCity Sailing. Once you have completed your lessons, you can spend a season sailing the boat you learned on, honing your skills and falling for the sailing lifestyle.

With over a decade of leasesharing experience under our belts, we have come to know what sailors are looking for. Whether you are a seasoned captain looking for a true classic to sail, or a novice seeking entrée into the sailing world, we have a boat and a program for you.

We look forward to hearing from you. If you have any questions, just shoot us an email at info@sailsharechicago.com or call (708) 481-3123.

Happy Sailing!

The Olsons


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