Adventure Collective
Water Activities & Sail & Swim Playpen Charter on Lake Michigan - Chicago

Water Activities & Sail & Swim Playpen Charter on Lake Michigan

Chicagoeasy

Difficulty

easy

Duration

4 hours

Fitness Level

All levels; moderate physical activity involved in swimming.

Overview

Set sail on Lake Michigan aboard the luxurious S/V Dragonfly for a four-hour adventure filled with scenic views and refreshing swims. Discover why this high-end charter is a top choice for water lovers in Chicago.

Chicago, Illinois

Sail & Swim Playpen Charter

All-Inclusive, 4-Hour Luxury Charter • Up to 7 guests • Perfect for bach parties & birthdays!

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About This Adventure

Embark on a thrilling 4-hour sail and swim adventure aboard the luxurious S/V Dragonfly, a 37' sailing yacht. Enjoy breathtaking views of Lake Michigan, a complimentary champagne toast, and a fully-equipped onboard experience. With a USCG-certified captain at the helm, create unforgettable memories with friends in a stunning setting.


4-hour Sail & Swim Playpen Charter

Unrestricted Access to S/V Dragonfly, Our 37' Luxury Sailing Yacht

USCG-Certified Captain Included

🎡 Departing From the All-New Navy Pier Marina

🥂 Complimentary Champagne Toast

🧊 Pre-Chilled 12-Pack of High Noon Vodka Seltzers


Overview

This Half-Day Charter includes adventurous sailing & summer swimming with friends on Chicago's Lakefront. Entwined with comfortable amenities aboard our 37' luxury sailboat, guests will have the unique chance to 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 champagne toast, 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

Wear Sunscreen

Protect your skin during midday hours while on deck or swimming.

Bring a Camera

Capture stunning skyline views and memorable moments from the boat.

Dress in Layers

Weather can change quickly; pack layers for comfort.

Hydrate Frequently

Swim and sail days can be dehydrating; keep water handy.

Local Insights

Wildlife

  • Gulls
  • Lake Michigan bass

History

Lake Michigan has been vital to Chicago’s development, with shipping and trade dating back over a century.

Conservation

The charter operators follow sustainable practices to minimize environmental impact and protect Lake Michigan’s natural beauty.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Sunscreen

Essential

Protects your skin from sun exposure during the boat trip.

summer specific

Swimsuit

Essential

Necessary for swimming in Lake Michigan.

summer specific

Hat & Sunglasses

Essential

Provide sun protection while on deck.

summer specific

Light Jacket

Warm layers for cooler weather on open water.

spring/fall specific