an analog experience for the discerning adventurer.
Not your grandma’s booze cruise.
Join Field Trip Chicago on a thoughtfully designed nautical adventure aboard our majestic 44' trimaran, Night Baseball. We’re a woman-led, one-of-a-kind sightsailing outfit for people who love laughter, value connection, and want to experience Chicago from a whole new perspective.
Not too bougie.
Not too basic.
Welcome aboard.
the boat
tri.ma.ran
/ˈtrīməˌran/
noun
a yacht with three hulls in parallel.
At Field Trip, we craft moments of wonder—rooted in nature, rich in connection, and gentle on the planet.
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
Drift back to when summer meant wind in your hair and stories by sunset.
Our family-friendly sails are perfect for wide-eyed kids, eye-rolling teens, and nostalgic grown-ups chasing real memories—no Wi-Fi required.
For Organizations
Swap boardrooms for broad horizons. Our corporate retreats blend relaxation and purpose, helping teams reconnect, recharge, and rethink what’s possible. With the Great Lakes as your meeting space, inspiration comes standard.
off-shore.
off-line.
on-point.
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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Go for it! Start with an hourly sail and customize the when, where, and how long. Rates may vary slightly based on the day and time, and we’re always here to help if you need a hand.
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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 and professional photography, this is the place to look. We’ve partnered with top local talent to help make your day truly unforgettable.
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Ready to book? Head to the calendar to lock in your sail. If your ideal date or time isn’t available, don’t worry—just call, email, or fill out a special request form. We’ll do our best to make it happen. We’ve got you.
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If your ideal date isn’t available—or you’re dreaming up something our booking tools can’t capture—this is the place to be. Fill out our special occasion request form, 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.”
Every adventure includes Captain + Crew, boat snacks from The Chandlery, and a cooler full of spirit-free ice cold refreshments.
BYO always allowed.
Some adventures have upgrades and add-ons built into the price.
If you’re interested in substituting one upgrade for another, just shoot us a text or email. We’re happy to work with you.
photo log
