an analog experience for the discerning adventurer.
Built with Care. Sailed with Style.
Field Trip offers considered sailing excursions along the Chicago Lakescape.
A woman-led, singular operation for those who value play, cherish connection, and delight in the pleasure of seeing familiar places with new eyes.
2025 Air + Water Show
〰️〰️〰️
August 16 +17
〰️〰️〰️
2025 Air + Water Show 〰️〰️〰️ August 16 +17 〰️〰️〰️
harbor happenings
Sold Out
field trip highlights
-
![]()
Sunrise Cruises
2hrs
Watch the city wake up from the water.
Join us for a peaceful early-morning sail. As the sun rises over Lake Michigan, enjoy calm waters, quiet skies, and a front-row seat to the most serene part of the day. We’ll bring the magic... the coffee.
-
![]()
The Playpen
+1
Your Floating Day Party Starts Here
Hop aboard Night Baseball and dive into one of Chicago’s hottest summer scenes—the Playpen. With good vibes, great music, and endless sunshine, this is your launchpad for wild memories and waterfront fun all day long. -
![]()
Night Lights
1.5hrs
The best view of Chicago, in all of Chicago.
The perfect spot from which to view the navy pier fireworks. Come for the view, stay for the show. What you'll enjoy: sunset behind the skyline, dusk illumination, and fireworks show. -
![]()
Night Sailing
2hrs
Sail out just far enough to watch breathlessly as the sun sets behind the silhouette of the skyline, the shroud of dusk gently slips over the sky, and the lights of the city snap awake in unison. End back in the harbor with a drink, dinner and a dip in the lake as fireworks rain down over Navy Pier.
-
![Chicago skyline with skyscrapers and lakefront view]()
Skyline Sails
2hrs
Want a transformative journey on the water without feeling like you’ve left Chicago? known as “inshore sailing”, this close-to-home cruise is less about the thrill and more about the view. gaze upon the same old city with new eyes, and fall in love all over again.
-
![Three people on a sailboat with the Chicago skyline in the distance during sunset.]()
Sunset Cruises
3hrs
The near-shore voyage of discovery thoughtfully designed for the slightly more adventurous spirit or those looking to learn the ropes. This lake excursion takes you out of the city without ever losing site of the skyline. Feel the thrill of the sail while still staying close to home.
-
![Sailboat with people wearing life jackets on open water under clear blue sky.]()
Learn the Ropes
4+
“Chicago Has a Great Lake” - the timeless statement is just as true today as it was in 1965. this tailored off-shore adventure is our most horizon-immersive day sail on the menu. discover just how great our lake really is, and the power it has to restore you.
-
![Colorful sunset over calm ocean waters with a silhouetted coastline in the distance.]()
The Hinterland
overnight
Sail.Scout.Sleep.Repeat. Our most ambitious offering, this multi-day adventure is sure to feed your fernweh. If you dream of steering into the horizon, sleeping under the stars, and exploring the hinterland, you’re in the right boat. literally and littorally.
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 and the only chartered 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
Trade boardrooms for open water.
Our corporate sails strengthen teamwork, build trust, and spark fresh thinking.
offshore offline on point
how it works
-
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.
-
Customize your timing, route, and duration. Rates vary slightly by day and time. Need help? We’re here.
-
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.
-
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.
-
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.
-
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
Experience the thrill of the skies and the calm of the lake all in one unforgettable day! Join us aboard for our exclusive Air & Water Show Sail, where you’ll enjoy front-row views of one of Chicago’s most iconic summer events – right from the water.