About Two Brothers Sailing

Since 2010 Two Brothers Sailing Adventures Chicago has been providing safe, fun and comfortable sailing charters. Our specialty is sailboat rental in Chicago. With a safe fleet of modern sailboats and fishing boats, our customers have a good selection of watercraft to rent or charter. We pride ourselves on providing new sailors with a true taste of the amazing lifestyle that is sailing. Seasoned sailors also get a chance to stretch their sea legs and participate in all aspects of the sail.


Sailboat Rental in Chicago

Whether you want to relax and soak in the sights and sun, or dig in and pull up the sails and man the helm, you will love every minute of your time aboard a TBSA charter.  Many of our guest enjoy the friendly service, open food and beverage allowances, music and good nature of the captains.  There are other sailboat rental companies in Chicago, but there are no other sailboat charter companies that will show you the good time of a Two Brothers Sailing Adventure!

There are more than just sailboats for rental or personal charters. We offer Full Party and entertainment services for personal use, corporate use, non-profit entertainment, sporting events and just about any group party you can think of. Our captains are easy to work with and will help your next sailing adventure become a memory to talk about for years.