the adventures

4 - 12hrs

Your gateway to fun, your Floating Day Party Starts Here
Hop aboard Night Baseball and dive into one of Chicago’s hottest summer scenes—the Playpen. With good vibes, great music, and endless sunshine, this is your launchpad for wild memories and waterfront fun all day long.

2hrs

The perfect end to the day, sail with us out onto the lake just far enough to take in the entire panoramic view of the city. Watch breathlessly as the sun sets behind the silhouette of the skyline, the shroud of dusk gently slips over the sky, and the lights of the city snap awake in unison. Finish off the adventure in the harbor with a drink, dinner and a dip in the lake as we watch the fireworks rain down over Navy Pier.

Best for families with kids age 7+

2hrs

Step aboard for a transformative journey on the water without venturing too far from shore. Known as “in-shore sailing”, this 2 hour close-to-home experience is less about the thrill and more about the view. After a short, easy breezy sail along the shoreline, you’ll spend a low-key afternoon hanging in the harbor with a packed cooler and our signature FieldTrip playlist. Cool off in the lake under the best view of the city - Swim, SUP or kayak until you feel refreshed. Look upon the same old city with new eyes, and fall in love all over again.

What you’ll get:

2 hrs of in-shore sailing

the best views of the skyline

harbor hang w/ swimming, SUP, and kayaking

a packed cooler of ice cold cans

boat snacks

boat jams

2 hours not long enough? Add extra hours in our add-ons section.

3hrs

The near-shore voyage of discovery thoughtfully designed for the slightly more adventurous spirit or those looking to learn the ropes. This lake excursion takes you out of the city without ever losing site of the skyline. Feel the thrill of the sail while still staying close to home.

What you’ll get:

3 hrs of in-shore sailing

hands-on experience sailing a 44’ trimaran

anchoring in the lake for swimming, snorkeling, kayaking, and SUP

a stocked cooler full of ice cold cans

boat snacks

boat jams

3 hours not long enough? Add extra hours in our add-ons section.

4+

“Chicago Has a Great Lake” - the timeless statement is just as true today as it was in 1965. This tailored off-shore adventure is our most horizon-immersive day sail on the menu. Discover just how Great our Lake really is, and the power it has to restore you. If you are in pursuit of a truly transformative experience with a significant nervous system overhaul, hop aboard.

Not suitable for anyone uncomfortable with awkward silence.

overnight

Sail. Scout. Sleep. Repeat. Hop aboard to catch a sweet ride out of the city without ever traveling a single road. Unlike anything else in Chicago, this full service multi-day adventure is our most ambitious offering. If you’ve ever dreamt of sailing into the open horizon, sleeping under the stars, and experiencing the national treasure just across our lake like never before, you’re in the right boat. literally and littorally.

What you’ll get:

Transportation across the lake to the Indiana Dunes National Lakeshore

Hands-on experience sailing a 44’ trimaran

360 degree horizon bath and nervous system reboot

Sunset, Stars and Sunrise (guaranteed at least 2/3)

2 Breakfasts, 2 lunches and 2 dinners, plus unlimited snacks, s’mores and drinks under the stars.

Guided hikes through the Dunes

Swimming, kayaking and SUP

Choice of sleeping aboard or sleeping rough on dry land

All gear, tools and equipment transported and set up prior to your arrival

Revelation and transformation

Memories that will last a lifetime