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

This is the option to choose to really make the sailing experience your own.  This option opens up more options, more choices, and more flexibility for you and your guests.

DURATION: This is where the choices begin.  Choose your preferred charter duration ranging from a minimum of 3 hours to a maximum of 12 hours.  We can schedule even longer charters, but charters in excess of 12 hours require our assistance to book.

OTHER CHARTERS YOU MIGHT ENJOY

Private
Day Sail

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Private
Sunset Sail​​

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Custom Sailing, Swimming & Grilling

 All custom charters are private.
​The passenger list is at your discretion.​​​

FEATURES

• Up to 6 passengers
• Flexible Duration
• ​Flexible Departure Times
• USCG Licensed Captain

SWIMMING: If you want to swim during your charter, then you've chosen the right option.  Swimming is allowed on charters of 3 hours or longer in duration. There are a few rules and restrictions that go along with swimming during your charter.

• First and foremost, for safety reasons, swimming is NOT guaranteed and is at the captain's discretion.  So, if swimming is an important factor in your charter, please reach out to us so that we can be sure to do everything in our power to provide you with an opportunity to swim.
• Swimming will only be allowed during daylight hours (between sunrise and sunset.)
• Swimming will only be allowed while the sailboat is at anchor.
• SWIMMING IS AT YOUR OWN RISK!  If any passengers wish to swim, then ALL passengers on board must sign a liability waiver and release prior to anyone swimming.  This is true for ALL passengers whether or not they plan to swim.
• All passengers must remain with the charter through it's entire duration.  No one may depart the charter by swimming to shore.  No one may depart the charter by swimming to another boat.
• No person will be allowed to join the charter at anytime between departure and return to our official boarding area in Monroe Harbor.

​GRILLING: ​Yes, we do have grills that you are welcome to use.  Grills are available by request on charters of 3 hours or longer in duration.  Like swimming, grilling is an activity allowed only while the sailboat is at anchor.  Please reach out to us if you intend to grill so that we can be sure the grill and propane tanks are on board prior to departure.  We do require one day's notice for grill requests.

CUSTOM DEPARTURES: Choose a departure time that works best for you and your guests.  The sailboat will be ready and waiting on according to your schedule.

CUSTOM DESTINATIONS: With advance notice, we can assist in scheduling a custom destination for the end of your charter.  Additional fees will apply.  Please reach out to us directly for options and details.

FLEXIBILITY: Custom charters allow for much more creativity and flexibility in your sailing experience.  Flexibility is the ultimate in luxury.  With no other passengers, there is no concern over conflicting preferences.  The sailing experience can truly be your own.  Food, beverage, music, course we sail, when we sail, it's all within your power to choose. 

We want each sail to be a fun and memorable experience for every person. In order to provide that unique and personalized experience, we will make every effort to provide additional services like decorating, photography, and catering upon special request. Please ask for details.​

Your Chicago sailing and offshore adventures start here!

STEP 1 - CHOOSE A SAILBOAT

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

$196/hr

WEEKDAYS
(Monday thru Thursday)
​Taxes are additional

$222/hr

WEEKENDS
(Friday thru Sunday)
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​

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BOOK s/v Bernard

Sailing Vessel Druid

Our 28 ft. Sailboat built by Shannon Boat Co.

$174/hr

WEEKDAYS
(Monday thru Thursday)
​Taxes are additional

$199/hr

WEEKENDS
(Friday thru Sunday)
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

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BOOK s/v Druid