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.

Nope. Our captain and crew will handle the technical stuff. You’re welcome to get hands-on if you’re curious — or just sit back and enjoy the ride.

That’s Rémy, our 4 year old Barbet! He loves the boat and often accompanies us on our sails, but if you prefer he stay on land, just let us know that ahead of time and we’ll be happy to arrange that.

For shorter trips, we’ll send a checklist before departure. In general:

• Non-slip shoes or sandals

• A windbreaker or light jacket (even in summer)

• A swim suit

• A change of clothes in case you get splashed (it happens)

• Water bottle, sunhat, sunscreen, and sunglasses

• A sense of wonder

For overnight trips, we’ll provide a full gear list. Tents, sleeping pads, and meals may be provided depending on the adventure.

Pretty much the same essentials as above. We get it—when you're traveling with little ones, it’s tempting to pack for every possible scenario. But trust us: less is more. Keep it simple. Bring the basics, don’t forget a sunhat, and be ready for anything. Most importantly, pack your patience—and hold on tight. You've got this.

Some trips include snacks, drinks, or full meals — this will be listed on the booking page. You’re also welcome to bring your own (just no glass, please).

Yes, our boat is equipped with a composting marine toilet (“head”). On overnight trips, we may also camp at designated sites with access to restrooms.

Absolutely. All Field Trips are led by licensed, USCG-certified captains with years of experience. Safety is always our top priority, and we’ll provide a full briefing before we leave the dock.

We sail rain or shine, but if conditions are unsafe — strong storms, high winds, or heavy fog — we’ll reschedule or offer a full refund. We’ll notify you as far in advance as possible.

Yes, on some day and overnight trips we’ll anchor and give you a chance to jump in. Life jackets are always available, and swimming is optional. Don’t forget your swimsuit.

• Cancellations made 7+ days in advance: Full refund

• 48 hours to 7 days: 50% refund

• Less than 48 hours: Non-refundable

If we cancel due to weather or unforeseen circumstances, you’ll receive a full refund or credit.

Yes, pending availability. Email us at least 48 hours before your scheduled departure.

Yes, the rumors are true.
On a yacht charter, it’s customary to tip the Captain and Crew between 15% and 20% of the charter fee. This gratuity is usually handed to the Captain at the end of your trip, who then shares it with the crew. The amount can vary depending on the length of your charter and the level of service provided.

That said—if we don’t dazzle, don’t tip. But honestly? We’ll be stunned if your experience is anything less than spectacular.

We’ll send you a full pre-trip guide with packing lists, expectations, and pro tips. Don’t worry — we’re here to make sure you’re comfortable, prepared, and inspired.

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