Field Trip Chicago is a series of curated analog adventures for those who want to trade screens for skyline, and WiFi for wind. We’re launching with a fleet of unique sailing experiences on Lake Michigan — all designed to help you slow down, tune in, and get outside.

At Field Trip Chicago, sustainability isn’t an add-on—it’s our foundation. We believe in the power of nature to restore, reconnect, and remind us of what really matters. That’s why every experience we create is designed to tread lightly on the earth while deepening our connections—with the planet, with each other, and with ourselves.

Our adventures minimize excess and maximize intention. By focusing on simplicity, quality, and presence, we create space to unplug from the everyday and tune into what’s real—starting with the quiet beauty of Lake Michigan, powered only by the wind.

We’re not just offering escapes. We’re cultivating meaningful moments that last—rooted in community, guided by care, and built to sustain both relationships and the environment. This is our Oath of Sustainability: to protect what we love while helping you reconnect with it.

When we originally curated the adventures, we had four groups in mind:

friends

romantic partners

families

organizational teams

But the truth is, they’re for anyone with a sense of curiosity and a spirit for adventure. You don’t need sailing experience to come aboard. Some longer trips may require light to moderate physical activity like hiking or camping — if so, we’ll make that clear in the trip description.

Well, that’s a tricky question. According to the Coast Guard’s formula, over 80 people could technically “fit” aboard. We haven’t put that math to the test—and don’t plan to—but rest assured, the boat never feels crowded during your adventure.

That said, it’s a bit of a moot point: per USCG Passenger Vessel Rules, we can host up to 6 paying guests at a time. Our crew can be as large as needed to ensure a smooth and enjoyable sail, but your guest list stays intentionally small—preserving the comfort, intimacy, and personalized nature of the experience.

We offer three main categories of experience:

• Harbor Hangs (by the hour): There are times when the harbor offers everything you’re looking for.

• In-Shore Cruises (1.5–3 hours): Think golden hour sails, city skyline views, and sunset vibes.

• Half or Full Day Adventures (4–8 hours): Extended voyages that may include anchoring for a swim, onboard meals, or exploring new shorelines.

• Overnight Field Trips (1–3 days): Off-shore adventures that sail to the hinterlands, hike remote trails, and camp on land or sleep aboard anchored near shore.