For over 33 years Fairwind's Sailing Yacht Lease Share Program has offered sailors the best sailing value anywhere.  Compare our program with others and you will see the Fairwind Difference.  Fairwind pioneered the lease share concept for sailing yachts in 1978 and has never been equaled in Safety, Convenience, Value, or Customer Satisfaction.  With Fairwind there are no hidden costs, no fine print, and no high pressure salesmen.  Fairwind makes sailing a breeze -- you sail the yacht of your choice, all season long, for a fraction of what it costs to rent or own. And it's easy as 1-2-3 . 

Chidragon - Beneteau 40

Fairwind features BENETEAU YACHTS, the most popular boats in the world, renowned for their beauty and seaworthiness.  Whether sailing with friends and family, hosting out-of-town guests, or entertaining business associates and clients, you will be proud to bring them aboard your yacht.

Choose your yacht from among Fairwind's Dragon Fleet.  Click on the following for photo albums and virtual tours of Fairwind's Beneteau 40,  Beneteau 37, Beneteau 373, and Beneteau 343.

Fairwind offers the most cost effective way to sail new and late model yachts anywhere.  Many of our skippers are former boat owners who made the move to Fairwind to get the most out of their limited time for sailing at a fraction of what it cost them to own their own boats.  Others find Fairwind provides the ultimate "staycation" for languorous days of sailing along Chicago's magnificent lakefront.  A nice sail, a nice dinner under the stars, a beautiful sunrise -- all are yours with Fairwind.  

Fairwind yachts are equipped with in-mast furling mainsails and roller furling genoas that allow all sailing handling to be done from the safety of the cockpit.  Wheel steering, trusty inboard diesel engines, and a full compliment of on-board electronics make Fairwind's famed Dragon Fleet a pleasure to sail.

You and your guests will also love the spacious cockpits and luxurious below-deck galleys and cabins -- perfect for entertaining or enjoying an overnight stay in Key Midwest.  

And, in keeping with Fairwind's unrelenting emphasis on safety, all Fairwind yachts exceed U.S. Coast Guard safety equipment requirements. 

With Fairwind you get safe, beautiful, well-equipped, and professionally maintained yachts.  No wonder Fairwind has been the choice of Chicagoland sailors for over 30 years! 

The award winning Beneteau 373 and 343 are equipped with a new patented pivoting pedestal wheel affording wide open cockpit access!

Fairwind offers three schedule plans, all of which are spread evenly from mid-May to mid-October.  Full schedules are 28 sails (11 weekend sails and 17 weekday sails); mid schedules are 21 sails (8 weekend sails and 13 weekday sails), and half schedules are 14 sails (6 weekend sails and 8 weekday sails).  Full schedules include free, unlimited "as available" sailing. 

Fairwind is the only lease share program anywhere to provide its skippers the opportunity to make up sails missed due to bad weather.  Why pay for missed sails?  Fairwind wants its skippers to get their maximum sailing time possible while not feeling pressured to go out on iffy days.    

Weekday sails (Tuesday through Friday) are 9:00 a.m. to 5:00 p.m. and 5:00 p.m. to 9:00 a.m.  For weekend sailing, Fairwind increases access to your yacht by offering three sailing periods: 8:00 a.m. to 1:00 p.m.; 1:00 p.m. to 6:00 p.m.; and 6:00 p.m. to 8:00 a.m.  Why pay for time you cannot reasonably use?  With Fairwind you get prime sailing times and full value for your sailing dollar.    

Sailing schedules are worked out individually with each skipper, not assigned randomly by some abstract formula.  Fairwind works personally with each skipper to ensure he or she gets a great schedule that suits his or her needs.  And our online scheduling helps skippers keep track of their sails and to trade sails freely among themselves.  Fairwind prides itself in providing maximum flexibility in scheduling and is dedicated to making sure its program works for you.  

Fairwind is the safest, easiest, and most cost effective way to sail anywhere.  Instead of spending their hard earned dollars and precious hours on maintenance and up-keep, Fairwind skippers just step aboard and sail away.  And with an ASA award winning sailing school on site, you know that professional advice and assistance is always at hand. 

When you sail with Fairwind it's All Play and No Work! 

The Fairwind Difference 

Sailing is Fairwind's full-time business, not a freelance sideline, and its customer service is unequaled.  Over 90% of Fairwind skippers are repeat customers, many having been with Fairwind for years, and the equation is simple:  Safety + Convenience + Value = The Fairwind Difference.

SAFETY  With Fairwind, safety comes first. Fairwind is owned and operated by a professional USCG Master Captain and award-winning certified ASA Sailing Instructor for whom safety is the first and only rule of seamanship. 

Fairwind's well-protected location in the northwest corner of Burnham Park Harbor offers the safest docking in Chicago.  And its 50-foot slips with walk-on access eliminate the dangers associated with climbing on and off of tenders or dinghies and picking up wet moorings. 

All Fairwind yachts are owned by Fairwind, so you are not getting on someone else's yacht where maintenance is outsourced to others.  We personally check and maintain our yachts on a daily basis.  All Fairwind yachts exceed U.S. Coast Guard safety requirements, and Fairwind holds American Sailing Association's elite Gold Standard award for vessel safety. 

With Fairwind, you never get on a neglected boat maintained only when something breaks, with a questionable engine, frayed sails, or loaded down with other people's stuff.  Fairwind provides you and your guests with new, safe, and immaculately maintained yachts. Guaranteed.

And all Fairwind yachts carry $2,000,000 liability coverage for the protection of you and your guests. 

CONVENIENCE  Fairwind is located in beautiful Burnham Park Harbor at the heart of Chicago's magnificent Museum Campus.  Make your yacht your base for exploring the Adler Planetarium, Field Museum, and Shedd Aquarium.  In the shadow of Soldier Field, Fairwind offers the best location in Chicago sailing, on and off the boat.  (Click here for maps and directions to Fairwind.)

All Fairwind yachts are moored in 50-foot walk-on slips, which means no long waits and no extra expense for a tender to ferry you and your guests to and fro, and no rowing back and forth in a dinghy.  With Fairwind you are not constrained by tender schedule but instead just walk on board your yacht and sail away.  And Burnham Park Harbor is Chicago's most accessible harbor, with ample parking right beside your yacht. 

VALUE  Fairwind is the best value in sailing.  Renting a midsized cruising yacht costs well over $100/hour.  Owning costs even more; easily $10-15,000 a year assuming you do all of the boat work yourself -- and this does not include boat payments.  Plus you have to handle all maintenance, storage, mooring, insurance, etc.

With Fairwind you avoid the costs and hassles of ownership or short term rentals and pay less than $30.00/hour for your own yacht.  This low cost includes Fairwind's rigorous maintenance, cleaning, fuel, pump-outs, etc. 

Fairwind's policy of allowing make-up days for sails missed due to bad weather adds up to huge savings for Fairwind skippers, and its walk-on access saves its skippers additional hundreds of dollars per season that they would otherwise pay for tender service for them and their guests. 

Fairwind has never charged an "initiation fee," and requires a straight-forward $1000 damage deposit that is fully refundable at any time a skipper leaves the lease share program (no parsing of your damage deposit or trying to pressure you into staying multiple seasons just to get part of your damage deposit back).  With Fairwind there's no fine print and no hidden costs, just added value.  

For the best sailing value anywhere, ask about Fairwind's Summer of Sail Package -- Award winning private instruction for two people leading to ASA's Basic Keelboat Sailing and Basic Coastal Cruising Certifications, combined with a summer lease share on a beautiful Beneteau yacht.  

Fairwind's commitment to customer service has been its hallmark from the beginning.  Fairwind's staff is known for its friendly and welcoming manner and is dedicated to providing the best sailing program anywhere. 

The Fairwind Difference?  See what our customers say!