Skyline views, smooth sailing, and a 52-foot yacht full of memories!

If you’re planning a celebration, a summer get-together, or just an unforgettable day on the water in Chicago, look no further than Live A Little Yacht Charter. I recently sailed with 10 of my best friends aboard a luxurious 52-foot yacht, and it was hands-down the highlight of our summer. As someone who has lived in Chicago almost all of her life, I can confidently say this was the most amazing thing we have done in our city!

Between the skyline views, the music, and the amazing company (shoutout to the crew!), it was the perfect way to experience Chicago in a whole new way. Whether you’re a local or just visiting, this is one of those “you have to do this at least once” moments. Save 10% with my code: thehonestpassport10 when booking at www.lalyachting.com

See reel of our experience here: Video

See photos aboard the yacht here: Photos

Why Live A Little Yacht Charter Is a Must

Live A Little Yacht Charter specializes in Chicago yacht rentals, with a focus on fun, flexibility, and unforgettable experiences. They offer:

Playpen parties
Bachelorette & birthday yacht rentals
Sunset sails
Downtown skyline cruises
And more!

Our 52-footer was spacious, sleek, and completely private. With room to lounge, dance, and snap 100 photos, it was the ideal setup for our crew. One of the best parts? This experience is BYOB. We brought all our own food, snacks, and liquor—everything from charcuterie and chips to seltzers, champagne, and cocktails. Best of all, they provided the ice, so our drinks stayed perfectly chilled all day.

There’s plenty of cooler space on board, plastic cups and utensils and the layout made it super easy to serve ourselves, hang out, and enjoy. Our yacht had a kitchen downstairs and a nautical themed bedroom to boot! Upstairs is where all the fun began! We enjoyed hanging out at the front of the yacht or snacking away in the back and enjoying comfortable lounging.

The Sailing Route: Skyline Magic & Downtown Awe

We started from Diversey Harbor, where we were welcomed by the friendly crew and got a quick tour of the yacht. Then we set sail—literally—into one of the most scenic city views in the country.

We cruised past:

The iconic Chicago skyline
Navy Pier
The Chicago River locks, which let us sail right into Downtown Chicago
And finally sailed down the Chicago River in style!

From floating alongside sparkling high-rises to dancing on deck with the lake breeze in our hair, every minute felt surreal.

An Unforgettable Day with Friends

Huge thanks to the Live A Little Yacht Charter crew—they were professional, upbeat, and totally on top of things while also letting us do our thing. They handled docking, steering, and safety with confidence, and were always nearby if we needed anything. It truly felt like we were on our own private floating oasis—with the added bonus of a supportive, fun-loving team making it all seamless.

🛥️ How to Book Your Own Yacht Charter in Chicago

Live A Little Yacht Charter – Chicago

📩 Email: justin@lalyachting.com
📱 Phone: 773-531-7093
📍 Departure Location: Diversey Harbor, Chicago
🌐 Website: www.lalyachting.com
📸 Instagram: @LALYACHTING

Whether you're planning a:

Celebration with friends 🎉
Birthday bash 🎂
Lakefront hangout 🐬
or just need an excuse to sail...

Live A Little has packages for every occasion! They are great for booking a fireworks cruise in the city as well!

Pro Tips for Your Yacht Day

Book early, especially for weekends and holidays
BYOB + bring your favorite snacks or catering setup
Sunscreen, sunglasses, and water shoes come in handy
Make a playlist—there’s Bluetooth on board!
Charge your phone—you’ll want lots of photos

Final Thoughts

Sailing with Live A Little Yacht Charter was one of the most exciting, unique, and effortlessly fun ways to celebrate with friends. Between the skyline views, dancing with friends, creating unforgettable memories, and relaxing with drinks on deck, it was a dream day we’ll all be talking about for years.

Whether you’re local to Chicago or visiting for the weekend, don’t miss your chance to live a little—literally.

See more of our yachting adventures here: The Honest Passport.

Sailing in Style: Live A Little Yacht Charter in Chicago