Semi-Private Sailboat Charters


Semi-Private Sailboat Charters First-Class Sailing for 2 – $199

Several Fireworks upgrades available …

 Morning Sails

May 13 – Sep 15 (Sat/Sun)- 9am

Sunset Sails

May 16 – Jul 22 – (M/Tu/Th/Su) : 7pm
Jul 25 – Sep 15 – (M/Tu/Th/Su) : 6:30pm

First-Class sailing

One of our beautiful sailboats.

Chicago Sailboat Charters offers Semi-Private sails so that groups of 2 or 4 can share a First-Class sailboat on an economy class budget. We put small groups together to share our fantastic sailboats that are 36′-39′ long, and limit the group sizes to 6. These boats can easily hold 8-10 people more than comfortably, so you know you will be cruising in comfort and style.
All Semi-Private sails are 2 to 2.5 hours (see below for duration info), and take place Saturday, Sunday, and Holiday Mornings, as well as Monday, Tuesday, and Thursday evenings for sunsets. Some other sailings, such as weekend afternoons and evenings, Friday nights, and Wednesday and Saturday fireworks, are offered when available.

Children must be at least 12 years old to sail on semi-private sails (unless you are a group of 6 – which means only your group is on the boat, in which case you must have at least 1 adult per child under 12 in your group). Seats are only sold in multiples of 2.

Semi-Private Season: May 13 through Sep 15 (Not valid 7/1-4, 8/19-20)
Sat/Sun sails in July and August are 2 hours, all others are 2.5 hours.