things to do in Wilmette, IL

Cruise a 47-foot Carver with space to relax, dine, and play your music

Hire a US Coast Guard licensed captain for your Chicago boat day

Tour and tasting for two with a tasting room reservation and wine

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Speed across Lake Michigan with your own music and skyline views

Taste Dublin’s doughnuts while uncovering city stories on foot

Bring your group together for an autumn outing on the farm

See Chicago's northwest suburbs and the Fox River from the air

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Private 40' Sea Ray yacht rental in Chicago for up to 13

Explore Chicago Chinatown on a 2026 USA Today 10Best History Tour winner

Taste Chicago classics and discover the stories behind the city’s signature dishes

Make your Chicago celebration a private day or night on the water

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks

Discover the journey from fresh grapes to wine during Chicago's harvest season

Eat your way through Chicago’s Chinatown with 5 seated tastings

See Chicago landmarks from the water on a private sightseeing outing

Walk Edinburgh’s Old Town and sample doughnuts and pastries in 2 hours

Explore several farm attractions with one weekend admission

Take in Chicago's parks, waterfront, and landmark sights in one ride

Build foundational kayaking skills on calm Chicago River waters

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

Discover Logan Square’s past through handcrafted greystones, historic churches, and ornate storefronts

Walk Chicago Chinatown and taste dishes from five Chinese regions