There is nothing - absolutely nothing -
half so much worth doing as simply messing about in boats. Kenneth Grahame, The Wind in the Willows

chicago skyline

Book a charter on our beautiful Catalina 34 for a fantastic sail.

Our 34 foot Catalina is set up and ready for your sailing pleasure. It's the perfect size and layout for a comfortable cruise along Chicago's stunning lakeshore. Join us with a few of your friends for a relaxing sail. We can accomodate up to 6 people with lots of room "kick back" and relax. The boat is equipped with cushioned cockpit seats, a cooler with ice, paper plates and cups, plastic wine glasses, eating utensils, and a stereo CD player with an iPod hookup.

And if Blue is more boat than you need, you can also charter our 24 footer, SloopCity 1, and combine a lesson with your charter - or just relax.

If you don't see the information you are looking for, just give us a call and we would be happy to answer any questions you have. We'll work to set up a schedule that works for you.

Charter now to take advantage of our special low rates:

Weekday/weekday evening rate (excluding Wednesday): $120 per hour
Weekend days and evenings: $130 per hour
Wednesday night fireworks: $140 per hour
Saturday night fireworks: $150 per hour

Our 24 footer, SloopCity 1, is still a bargain to charter:

Weekday/weekday evening rate: $80 per hour
Weekend days and evenings: $90 per hour

All charters will have a 9% City of Chicago Amusement Tax added.

Call us at 312-401-8278 to set up your charter today.


Our Sailing Instruction program is the best Chicago has to offer!

We at SloopCity Sailing believe we offer the best sailing instruction in the area. Our classes are resonably priced, comprehensive, and we strive to assure a safe and fun experience for everyone. With the SloopCity 1 class, you will also receive a copy of US Sailing's "Basic Keelboat" book, pertinent class materials, and a knot tying line. Our 24 foot instruction boat, SloopCity 1, is responsive, comfortable, well rigged, and safe for Lake Michigan conditions. Sign up for one of our classes now - you'll love it!

Not sure if sailing is for you? This is the perfect opportunity to get out there and discover what sailing is all about with our "Intro to Sailing" class. Join with a couple of your fellow "fence sitters" for an day or evening of instructional sailing along our beautiful shoreline. You'll love sailing as much as we do.

Just bought a boat and need a little help getting comfortable with it? Need a little practice with docking, sail trim, or anchoring? We can help! Just give us a call and we can take you out for some private instruction - working on the specific areas you need help with.

Sign up for a class now and get your summer in gear!

SloopCity 1 - Basic Sailing Class. 15 - 16 hours: $450
SloopCity Skipper - Intermediate Sailing. 12 hours: $400
Intro to Sailing: 3 hours. 4 person max. $80 per person.
Private Instruction: On our boat: $80 per hour. On your boat: $70 per hour

See the detailed listing of our classes on the "Sailing Instruction" page. If you don't see something that fits your needs, just give us a call and we will work out a plan for you.