CHICAGO'S PREMIER ​SAILING EXPERIENCE
​AND PRIVATE SAILING CHARTER

Join us for a very special combination of a breathtaking sunset sail ending with a spectacular finale of the Navy Pier Fireworks.  This is the ultimate sail for romantic getaways, a night out with friends, or entertaining clients.

Checkout our CUSTOM CHARTERS for options like SWIMMING and GRILLING.
and
Checkout this article by Mark Stevens about Chicago in the June 2019 issue of Canadian Yachting Magazine
featuring a sail with Captain Mike on our Shannon 28 sailboat named Druid. 

Come Sailing is Chicago's premier sailing experience and private sailing charter offering a variety of boat rides, sailing charters, sightseeing tours, swimming trips, and customer private charters on Lake Michigan.  Take a break, Come Sailing, and let the wind blow away the stress of everyday life!

Your Chicago sailing and offshore adventures start here!

Day Sail

FOR DETAILS / BOOKING
CHOOSE CHARTER TYPE

SHARED

PRIVATE

Private
​Sunset & Fireworks

This is a private charter.
​The passenger list is at your discretion.​

FEATURES

• Up to 6 Passengers
• Three-hour Charter *
• Departs @ 7:00 PM
• USCG Licensed Captain

* Extend your time on the water with a
CUSTOM CHARTER

Sunset Sail

FOR DETAILS / BOOKING
CHOOSE CHARTER TYPE

SHARED

PRIVATE

STEP 1 - CHOOSE A SAILBOAT

Sailing Vessel Bernard
​
Our 36 ft. Sailboat built by Catalina Yachts

$588

WEDNESDAYS
Taxes are additional

FEATURES

• Instant booking confirmation.
• Spacious design with plenty of room for 6 passengers.
• Large cockpit area with comfortable seat cushions.
• Additional seating on sizable forward deck.
• Swimming options available.
• Options available for use of gas grill.
• See more details on s/v Bernard​

​

BOOK s/v Bernard

Sailing Vessel Druid

Our 28 ft. Sailboat built by Shannon Boat Co.

$522

WEDNESDAYS
Taxes are additional

FEATURES

• Classically charming sailboat.
• Luxuriously adorned with elegant teak.
• Comfortable seat cushions
• Additional seating built into aft cockpit rail.
• Sporty sailing characteristic with a bit of heel (lean).
• Room for 6, but most comfortable with 4 passengers.
• See more details about s/v Druid

​

BOOK s/v Druid