Friday 16 April 2021
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Chicago Insider: Bruce Randall on why sailing on Lake Michigan is an unrivaled city experience

Bruce Randall
Captail of the Tall Ship Windy on Navy Pier (

How long you’ve lived here: I moved to the Chicago area in 1993.

What you like best about Chicago: The people are what make this city great. One winter here will convince most that it is not the weather, but the summers on Lake Michigan are great.

Best meal you’ve had recently: I had a great Indian meal at the India House on Grand Ave.

Favorite big-name restaurant: Riva’s, the best seafood in Chicago!

Favorite “hidden gem” restaurant: Miceli’s Deli & Food Mart is my favorite lunch place. Been going there for 10-plus years. Let Lou know that Bruce sent you! It’s in Little Tuscany, one block east of Western Ave.

Best sports bar to catch the game: Maybe because it is close, I like the Billy Goat Tavern on Navy Pier.

A great night out with friends usually includes… a ride on a tall ship, and then a couple of rum drinks.

Favorite store or best shopping area: I’m not much of a shopper myself, but my wife loves Oak Brook Mall. And she wanted me to add this: “Locals know that the best shopping is away from downtown in the trendy, cool neighborhoods all over Chicago like Old Town, Bucktown and Lincoln Park, where the shopping and people-watching are great, and the eateries and bars are something special.”

The best way to spend a summer Saturday in Chicago: Sailing. I prefer to be on one of the two great tall ships here in Chicago, especially when they are firing their cannons! My wife included riding the motorcycle on Lake Shore Drive and watching the sunset at the end of Planetarium Drive.

One thing every visitor must do here: After a lake tour, catch the Ferris Wheel on Navy Pier. It has very cool views.

While in Chicago, don’t bother… to get one of the deep-dish pizzas. I grew up in Boston, so I must admit to being partial to thin-crust pizza.

Secret Chicago spot: Can’t tell you. If I did, it would spoil it. Sorry.

Underrated activity in the city: “Whale watching” Friday happy hour sails on the Tall Ship Windy. Once you have done it, you will want to do it again.