Lake Michigan: Chicago’s greatest public commons.
Always here. Always yours.
You may have forgotten.
We're here to remind you.
Field Trip is a community on Chicago's shared civic landscape, hosting analog adventures on the water, where the city hits different.
You haven't fully experienced Chicago until you've experienced it from the lake.
Take A Field Trip
Curiosity is the only credential.
Participation is the expectation.
Stewardship is the culture.
Belonging is the outcome.
Introducing
DAYBREAK
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a field trip series
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DAYBREAK 〰️〰️〰️〰️ a field trip series 〰️〰️〰️〰️
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![chicago skyline as seen from the boat at golden hour]()
The Urban Scout
2 hours
The city looks different from out here. This close-to-shore sail keeps the skyline in sight while putting water under your feet. Less about the distance. More about the shift in perspective.
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![sailboat at dusk with silhouette of the Chicago skyline in the background]()
The Lakescaper
3 hours
Far enough out to feel the lake breathe. Close enough to watch the city shrink behind you. For the ones who want a little more horizon in their lives.
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![blue and white "chicago has a great lake" poster]()
The John Massey
half day
Named for the Chicago designer who told this city in 1966 that it had a great lake. He was right then. He's right now. This is our most horizon-immersive sail — the one that takes you far enough out to understand what he meant.
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![Colorful sunset over calm ocean waters with a silhouetted coastline in the distance.]()
The Hinterland
overnight
Sail. Scout. Sleep. Repeat. If you've ever wanted to steer into the horizon and not come back until morning — this is your sail. The Great Lakes at night are something you don't forget.
“Logging off and connecting is the new luxury.”
— Harper's Bazaar
a sail for friends
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a sail for families
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a sail for teams
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a sail for first timers
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a sail for the chronically overstimulated
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a sail for Chicago
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a sail for ALL
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a sail for friends 〰️ a sail for families 〰️ a sail for teams 〰️ a sail for first timers 〰️ a sail for the chronically overstimulated 〰️ a sail for Chicago 〰️ a sail for ALL 〰️
the boat
tri.ma.ran
/ˈtrīməˌran/
noun
a yacht with three hulls in parallel.
Like a monohull with training wheels, Night Baseball is Chicago’s most stable sailing charter. One boat. Six guests. Chicago’s only trimaran.
For Friends
Celebrate anything—or nothing at all—on a sail made for unforgettable moments with your favorite people.
For Couples
From golden hour cruises to starlit overnights, our romantic getaways set the scene for connection, reconnection—and maybe even a little Love Boat magic.
For Families
Rediscover summer’s magic. Our family-friendly sails are perfect for wide-eyed kids, skeptical teens, and nostalgic grown-ups chasing memories that never fade.
For Organizations
Say thanks in style. Our appreciation sails turn gratitude into a memorable experience on the water. Show your clients or team how much they matter with an extraordinary sailing adventure.
Whatever the occasion, do it out here…
how it works
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We get it—you don’t need one more thing to plan. That’s why we’ve curated a collection of our favorite, most-loved sails. We’ve handled the details and done the thinking for you, so all you have to do is show up and enjoy a seamless, stress-free adventure.
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Customize your timing, route, and duration. Rates vary slightly by day and time. Need help? We’re here.
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Sailing makes us hungry. After months of culinary trial and error, we’ve figured out the best boat-friendly bites—and teamed up with some of Chicago’s finest to bring them on board.
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Some moments deserve more than a playlist and a phone camera. When your celebration calls for live music, professional photography or other finishing touches, consider bringing our artists on board. We’ve partnered with top local talent to help make your day truly unforgettable.
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Ready to book? Use the calendar to lock in your sail. If your ideal date or time isn’t available, just reach out—we’ll do our best to make it happen.
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If you’re dreaming up something our booking tools can’t capture, look for our Special Request button, share your vision, and our events team will do everything they can to bring it to life. We love a good challenge and don’t believe in “impossible.”
What’s Included:
Every adventure includes a licensed Captain + Crew, curated boat snacks from The Chandlery, and a cooler stocked with ice and both still + sparkling water.
All adventures are private boat charters for up to 6 people.
BYO is always welcome.
Some trips include premium upgrades or add-ons in the base price.
Want to swap something out? Just shoot us a text or email — we’re happy to tailor your sail.
photo log
