Field Trip Chicago is a community-focused sightsailing outfit offering curated nautical adventures aboard our one-of-a-kind 44' trimaran, Night Baseball. We provide transformative, upscale experiences on Lake Michigan, from serene coastal cruises to breathtaking offshore excursions. Tailored for both seasoned sailors and curious landlubbers alike, FieldTrip reconnects city-dwellers with nature, elevating the way Chicagoans experience their lake.

Each charter includes a professional crew—captain and skippers—along with customizable itineraries and access to a curated network of local partners who can add that perfect finishing touch to your bespoke sailing experience.

Let’s set sail!

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