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.


USCG Captain

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.

Fairwind is the only program anywhere to offer makeup sails for sails missed due to bad weather. Our business model is based on seamanship, not maximizing profit. We want our skippers and their guests safe and never want our skippers to have to choose between going out in questionable conditions and losing a sail.

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.


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.

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.


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.

After some rather discouraging experiences with other organizations, it was wonderful to find Fairwind. Simply put, Fairwind’s perfect upkeep and management of their fleet leaves the sailor free to worry only about how deeply they can appreciate their sailing experience.

–Dave A.

That’s the Fairwind Difference!