Now accepting applications for Summer 2025! Thank you to our many returning Dragoneers – you’re the best!
For 47 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, no “initiation fee,” 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.
It’s easy as 1-2-3
Step One: Pick your Yacht
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.
Fairwind’s Dragon Fleet currently includes: Chidragon, a Beneteau 41; Dragonfly, a Beneteau 38.1; Silver Dragon, a Beneteau 37; and Flying Dragon, a Beneteau 373. The Dragon Fleet is docked in 50-foot, walk-on slips in the northwest corner of Burnham Park Harbor at the heart of Chicago’s Museum Campus. Fairwind’s customers love the safety and convenience of walk-on access (no dinghies or tenders to deal with), and the ample close-by parking.
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 complement 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 47 years!
I look forward to our sixth season of time sharing with Fairwind. It is great to have sailing times that you just have to accommodate out of your busy schedule, to do what you enjoy and to bring friends and business colleagues with you for a lovely time on the water – especially on Weekday afternoons! The lack of responsibility for the boat other than during the time you have it is wonderful – Ben takes great care of the boat and all that goes with it.
–John C.
Step Two: Pick your Schedule
Fairwind offers three schedule plans, all of which are spread evenly from late-May to mid-October. Full schedules are 27 sails (11 weekend sails and 16 weekday sails); mid schedules are 19 sails (8 weekend sails and 11 weekday sails), and half schedules are 13 sails (5 weekend sails and 8 weekday sails). Full schedules include free, unlimited “as available” sailing with 24 hour advance notice.
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 on providing maximum flexibility in scheduling and is dedicated to making sure its program works for you.
Step Three: Go Sailing!
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 upkeep, 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 are always at hand.
There are few people – myself included – who have the time to own a sailboat. My wife and I don’t want to spend what spare time we do have maintaining a boat and we have enough other interests that we don’t want to spend every spare moment in the summer on a sailboat. Fairwind is the perfect solution – we step on a boat clean, rigged and ready to sail and go sailing. No worries about winterizing – no worries about maintenance – and no guilty conscience because we aren’t fully using our very expensive asset.
–Pat P.
When you sail with Fairwind it’s All Play and No Work!
Chidragon — Beneteau 41
| 27 sails | $9875 |
| 19 sails | $8175 |
| 13 sails | $6775 |
Dragonfly — Beneteau 38.1
| 27 sails | $9675 |
| 19 sails | $7975 |
| 13 sails | $6575 |
Silver Dragon — Beneteau 37
| 27 sails | $8575 |
| 19 sails | $7075 |
| 13 sails | $5975 |
Flying Dragon — Beneteau 373
| 27 sails | $7475 |
| 19 sails | $6475 |
| 13 sails | $5775 |
The above rates include Fairwind’s unique opportunity for make up sails missed because of bad weather — a Fairwind exclusive. All lease share rates are subject to a 9% Chicago Transaction Tax. A fully refundable, $1500 damage deposit is required before sailing, which is fully refundable if you don’t renew after your first season. Fairwind does not hold back damage deposits if you don’t stay for more than one season like some other programs. With Fairwind you get simple, fair pricing. All 27 sail schedules include free, unlimited as-available sailing.
Summer of Sail Package: Combine award-winning private instruction for two people leading to ASA’s Basic Keelboat Sailing and Basic Coastal Cruising certifications with any of the above lease share options for a low flat rate. Save hundreds of dollars on private instruction! Please contact us for more information about the Summer of Sail Package.