News Archive

Fairwind Sail Charters Welcomes New Beneteau 41

Fairwind Sail Charters welcomes a new addition to the best sailboat fleet in Chicago. The 2016 Beneteau 41 is designed by naval architects Finot-Conq and Associates. It features a sleek low profile cabin with long coachroof windows and a continuous chine over the length of the boat. Major highlights of this beautiful yacht include a luminous interior plus an [continued…]

Picture Perfect Sailing with Fairwind Sail Charters

With the exception of a cool and rainy start, summer 2015 has provided picture perfect sailing. It was a season that saw a record number of students graduate from Fairwind’s award winning American Sailing Association sailing school, many happy skippers enjoying the beautiful Dragon Fleet, and lovely private charters for both locals and out of town [continued…]

Fairwind Makeup Policy Stands Out

Fairwind Sail Charters always puts safety first, which is why it is the only sailing lease share program to offer makeup sails to skippers who miss a sail due to bad weather. “I never want a skipper to feel a financial pressure to go sailing in poor conditions. I want our skippers to stay safe and get the [continued…]

Spring Ahead to your Sailing Future!

Get a head start on your sailing future with Fairwind Sail Charters. Chicago’s oldest American Sailing Association certified sailing school and the number one choice for cruising sailors for almost forty years. Learn to sail with the best and be ready for wherever your sailing future leads, whether it is sailing the Great Lakes on [continued…]

Fairwind Offers Early Bird Specials for 2015!

Fairwind Sail Charters is now accepting applications for its 2015 season. In celebration of its 37 years as Chicago’s premier sailing yacht lease share program, Fairwind is offering special pre-season pricing for sailors who sign up by November 15, 2014. For almost forty years, Fairwind’s beautiful boats, excellent location, and unsurpassed customer service have made it the choice of discerning sailors. [continued…]

Fairwind Distinguished by Make Up Policy

Fairwind Sail Charters’ sailing yacht lease share program stands alone in offering make up sails for sails missed due to bad weather.  Fairwind Sail Charters believes that sailors should never have an economic incentive to sail in questionable or unpleasant conditions.  This summer has once again confirmed the value of this emphasis on safety — Fairwind’s skippers have not forfeited a single sail due to the [continued…]

Summer Romance Blooms on Dragon Fleet!

Fairwind Sail Charters was honored to be part of a wonderful wedding proposal this past weekend on Chidragon.  In addition to being Chicago’s premier sailing yacht lease share and sailing school, Fairwind has become quite the engagement destination.  This is our seventh wedding proposal, and all of the beautiful brides-to-be have said “Yes!”  Could the Dragon Fleet be the new Love [continued…]

Location, location, location

What is true of your home on land is true of your home on water.  Fairwind Sail Charters has the best location in Chicago sailing.  In Burnham Park Harbor, at the heart of the Museum Campus, right across the street from the Shedd Aquarium and the Field Museum.  The Dragon Fleet rests in 50 foot [continued…]

Dragon Fleet Hits the High Seas!

Fairwind Sail Charters kicked off the 2014 season in style.  Beautiful day, beautiful boats, and of course beautiful people!  Fairwind’s lease share program is the oldest (and best) in Chicago.  Founded in 1978, Fairwind Sail Charters is also the oldest ASA certified sailing school in Chicago.  Don’t get left at the dock — contact Fairwind today [continued…]

Celebrate Spring in Key Midwest!

Our first 70+ degree day here in Key Midwest this season!  Definitely time to shake off the winter doldrums and start gearing up for sailing season.  Whether you are a new sailor looking for sailing lessons or an Old Salt looking for Chicago’s best sailing value, make Fairwind Sail Charters your home port.  Chicago’s oldest American [continued…]