Adventure Collective
Lakefront Water-Activities: Wedding Party Cruise Experience - Chicago

Lakefront Water-Activities: Wedding Party Cruise Experience

Chicagoeasy

Difficulty

easy

Duration

4 hours

Fitness Level

Accessible for most guests, minimal physical activity required

Overview

Celebrate your special day on a private sailboat cruising Lake Michigan, with stunning skyline views and a customizable itinerary. Perfect for weddings and special gatherings!

Chicago, Illinois

Wedding Party Cruise

4 Hour Sail & Swim • Perfect For Bachelor & Bachelorette Parties

Select participants and date

About This Adventure

Embark on a memorable 4-hour private charter aboard a luxurious 37' sailboat, guided by a USCG-certified captain. Enjoy stunning views of the Lakefront, swim at the Playpen, and indulge in your favorite BYOB snacks. Experience the comfort of a fully-equipped yacht while creating unforgettable memories with your guests.


4-hour Private Charter

37' Luxury Sailboat

USCG-Certified Captain Included

🎡 Departing from the all new Navy Pier Marina

🥂 BYOB & Snacks


What you'll do

Our private Wedding Party Cruise will take you & your guests on a favorable sail along the gorgeous Lakefront, giving a unique perspective to the city and a chance to swim at the Playpen. Entwined with comfortable amenities aboard our 37' luxury sailboat, guests will experience Lake Michigan from a privately owned, meticulously-maintained sailing yacht.

What's Included

✅ USCG-Certified Captain trained in First Aid and CPR.

✅ Private use of our fully-permitted, fully-insured sailing yacht.

✅ Complimentary beverages and snacks on board.

✅ Fully stocked kitchenware, fridge and bathroom.

✅ Stereo surround sound speakers with Bluetooth connection.

✅ Swim platform with ladder, life-jackets, noodles, floaties & towels.

❌ NO Separate captain fee

❌ NO Fuel and docking fee

❌ NO Damage/cleaning deposit

FAQ

🎒 What should I wear or pack?

We do our best to have on board everything you might need, some personal items to keep in mind include:

  • Rain jacket or layers for cooler days
  • Boat shoes, sandals, or non-black soled tennis shoes
  • Bathing suit for swimming

🍾 What food and drink can I bring on the boat?

You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering for an added fee.

⚡ What if there is bad weather?

If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.

❓ Where is your full list of FAQs?

You can see all of our FAQs here on our website


logo On A Boat Sailing, LLC info@onaboatsailing.com 312.619.7858

Adventure Tips

Arrive Early

Make sure to arrive at least 30 minutes before your scheduled departure time for a smooth check-in.

Bring Sun Protection

Sunscreen, hats, and sunglasses are essential for comfort during daytime cruises.

Pack a Personal Cooler

Bring your own beverages and snacks in a small cooler for convenience and variety.

Check the Weather

Monitor weather conditions prior to the trip to ensure a safe and enjoyable experience.

Local Insights

Wildlife

  • Seagulls
  • Herons

History

Lake Michigan has been vital to Chicago’s development as a port city and has hosted numerous historic events and vessel explorations.

Conservation

The company promotes environmentally responsible boating practices, including waste management and minimal disturbance to local wildlife.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Sun protection

Essential

Sunscreen and hats will keep you comfortable during sunny hours.

summer specific

Swimsuit

Essential

Ideal for swimming at the Playpen stop.

summer specific

Light Clothing Layers

Layered clothing for changing weather or cooler evenings.

Camera or Smartphone

Capture memorable moments of the cruise.