Other Deals That Might Interest You


Two Sailing Classes for One, or One Sailing Class for Two or Four from Skyline Sailing School (Up to 52% Off)

Skyline Sailing School

from $119
Value Discount You Save
$240 50% $121
Give as a Gift
Over 20 bought
Limited quantity available

In a Nutshell

ASA-certified captain lets students try steering and moving sails in an on-water class, and teaches sailing principles in a classroom lesson

The Fine Print

Expires 90 days after purchase. Limit 1 per person, may buy 1 additional as a gift. Limit 1 per visit. Valid only for option purchased. Reservation required; subject to availability. 48hr cancellation notice required. Customers must know how to swim. 250lb weight max per customer. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Commuting via sailboat has a number of advantages: there are no traffic jams, it's OK for the hitchhikers to have hooks for hands, and if you hit a deer it's definitely the deer's fault. Steer clear with this Groupon.

Choose from Three Options

  • $119 for an Explore Sailing course and an Intro to Sailing course for one (a $240 value)
  • $119 for an Explore Sailing course for two (a $240 value)
  • $229 for an Explore Sailing course for four (a $480 value)

The 1.5-hour open-water Explore Sailing course allows students to test the basic operations of a boat: they may practice raising, lowering, and trimming the sails, as well as steering at the helm. Each boat holds up to four students, allowing for private or semiprivate lessons depending on the number of attendees.

During the 6-hour Intro to Sailing course, which is based on the American Sailing Association's Sailing Made Easy manual, students receive classroom instruction on sailing terminology, the dynamics of wind, and principles such as points of sail and basic knot tying.

Skyline Sailing School

Jessica Ferris can trace her interest in sailing back to her childhood in Chicago and northern Michigan, where she plied Lake Michigan's waters with her family. As she grew up, she expanded her boating territory to the Gulf of Mexico, the Caribbean, and the Atlantic and Pacific Oceans. As an adult, she brought her talents home to Chicago as an ASA-certified keelboat captain and the founder of Skyline Sailing School. Here, she passes on her seafaring knowledge in classroom courses that teach sailing principles such as basic terminology, rules of open-water travel, points of sail, knot tying, and choosing the right shoulder parrot. She also engages students with hands-on open-water classes aboard 26-foot keelboats, which begin with an exploration of basic sailing skills and progress to lessons in more advanced maneuvers.

  1. 1

    Skyline Sailing School

    6400 S Promontory Dr.

    Chicago, IL 60649

    Get Directions

Classes and lessons, from horseback riding to wine tasting
Gear and getaways for outdoor adventures, from hiking to ski vacations
Outdoor activities, from cycling to sailing
By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.