What to Expect on Your First Private Sailboat Charter in Chicago

Never been on a sailboat before? You are in good company. Many of our guests are first-timers, and no sailing experience is needed. Here is what a private charter with Windy City Sailing looks like from the dock to the sunset.

Your captain and crew handle everything

Every private charter for up to six guests includes a licensed and experienced captain and crew. They manage navigation and safety while you relax. You can chat, take photos, or simply enjoy the breeze. Charters depart from Belmont Harbor, and the minimum charter length is three hours, with longer custom outings available.

What to wear and bring

Wear comfortable, weather-appropriate clothing and soft-soled, non-marking shoes. Temperatures on the lake can change quickly, even on a warm Chicago summer day, so layers are a smart idea. Guests are welcome to bring their own food and beverages, and a cooler with ice is available onboard. Alcohol is generally permitted for guests of legal drinking age, though the captain does not drink while operating the vessel.

Comfort onboard

Our 40-foot Beneteau sailboat Nebula comfortably seats up to ten guests, with cushioned seating, a large bimini sunshade, an onboard restroom, bottled water and a Bluetooth sound system so you can play your own music. Below deck you will find air conditioning, a galley with a microwave and sink, and a flat-screen TV. On warm days guests can swim off the swim ladder and rinse off afterward with the hot shower on the swim deck, when conditions allow.

What you will see

Cruising the Chicago lakefront gives you a view of the skyline that you simply cannot get from land. Guests enjoy the city towers, Navy Pier, the beaches and, on an evening charter, a Lake Michigan sunset that is hard to beat.

Weather and safety

Safety always comes first. If conditions on the lake are unsafe, your charter may be rescheduled or adjusted. Children are welcome aboard, and life jackets are provided.

Ready to set sail for the first time? Visit windycitysailing.com or tap Book Now to reserve your date. We have been welcoming first-time sailors and returning guests aboard for two decades.