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Family Boat Charter Chicago

Enjoy a private Lake Michigan cruise with your family and see Chicago from the water.

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Private charters from Montrose Harbor. Restroom onboard. No sailing experience needed.

Young child smiling on a boat wearing a red life vest during warm golden-hour light, with family and snacks nearby

A Relaxed Family Experience on Lake Michigan

A private sailing charter is a simple way to spend time together as a family while enjoying Chicago from the water. The experience is scenic, relaxed, and easy to enjoy without needing any sailing experience.

It is a good fit for visiting relatives, family celebrations, parents with kids, and groups who want a quieter alternative to crowded tour boats.

Why it's a fit

  • Your family’s trip—not a megaphone tour with a hundred other passengers.

  • There’s a restroom on board, which matters with kids or longer outings.

  • Everyone gets the skyline moment, from little ones to grandparents.

  • You don’t need to know how to sail; the captain handles the boat.

  • The day moves at your group’s speed, not a fixed tour timetable.

Recommended Charter Options

What to Expect

  1. Meet at Montrose Harbor

    Arrive at the harbor and meet your captain near the boarding location.

  2. Board the boat with your family

    Help kids and adults get settled with gear stowed safely.

  3. Review a short safety briefing

    Your captain will review basic safety information before leaving the dock.

  4. Cruise Lake Michigan

    Enjoy skyline views, light conversation, photos, and relaxed time on the water.

  5. Enjoy skyline views and relaxed time together

    Give everyone skyline views and relaxed time together on the water.

  6. Return to the same dock

    Your charter ends back at the original boarding location.

Planning Tips

  • Bring layers because the lake can feel cooler than land.

  • Bring simple snacks and drinks.

  • Bring sunscreen, sunglasses, and any kid-specific essentials.

  • Choose a daytime cruise for the easiest family experience.

  • Follow all captain safety instructions while onboard.

What's Included

  • Private use of the sailboat

  • Experienced captain / captain arrangement

  • Safety briefing before departure

  • Required safety gear onboard

  • Restroom onboard

  • Cooler/storage space

  • Boarding instructions before your trip

  • Weather monitoring before departure

Good to Know

This is a private sailboat charter, so guests board from the dock and move around a real boat. Children should be supervised by adults at all times.

FAQ

Is this good for families?
Yes. A private Lake Michigan cruise is a relaxed way for families to enjoy Chicago from the water.
Can kids come onboard?
Yes, kids can come onboard when accompanied by adults. Safety gear and supervision are important.
Is there a bathroom onboard?
Yes. There is a restroom onboard.
Do we need sailing experience?
No. No sailing experience is needed.
What should we bring?
Bring layers, sun protection, simple snacks, and anything your family may need during the charter.

Plan a Family Sail in Chicago

Enjoy a private Lake Michigan cruise with skyline views and time together on the water.

Check Availability