the adventures

2hrs

A transformative journey on the water—without ever leaving Chicago. Known as “in-shore sailing”, this coastal cruise is less about the thrill and more about the view. Gaze upon the same old city with fresh eyes, and fall in love all over again.

Perfect for families with little ones. A nice balance of sailing, snacking and swimming.

3hrs

A near-shore voyage of discovery, designed for the curious and adventurous. Learn the ropes, feel the power of the wind, and sail just far enough to leave the city behind—while keeping the skyline in view.

Great for families with teens, friend groups, and teams looking to strengthen connection and collaboration.

4+

“Chicago Has a Great Lake” - the timeless statement is just as true today as it was in 1965. Our most horizon-immersive sail, this offshore adventure invites you to rediscover just how Great our Lake really is—and the quiet power it holds to restore.

Ideal for those seeking presence, perspective, and a true reset.

Not recommended for anyone uneasy with stillness, silence, or too much sky.

overnight

Sail. Scout. Sleep. Repeat. Our most ambitious offering yet—an all-inclusive, multi-day sailing adventure designed to satisfy even the deepest wanderlust. If you dream of chasing the horizon, sleeping beneath the stars, and exploring the hinterland, you're in the right boat—literally and littorally.