Twilight Boat Cruise: Your Next Date Night

Important PSA: Only a few weeks of summer remain. Related PSA: Everyone’s favorite architecture boat tour now offers voyages by night. So how about charting one more date night before summer ends? Here’s your three-step plan to doing it right.

Step One: Get Something Nice
Begin the evening with a pop in to the Chicago Athletic Association Hotel’s newest addition, Madison Hall. They’ve got things she’ll love: Laura Lombardi jewelry, Illesteva sunglasses and smart tote bags from Bags in Progress, while you can pick up a comfy new tee by Reigning Champ. This is also the sort of night where their Christine Noelle floral-shop-in-shop will come in handy. Foolproof start.

Step Two: Get on a Boat
The one thing locals loves as much as tourists: The Chicago Architecture Foundation’s river tour. And those skyscraper lovers have done us all a solid by adding nightly twilight cruises. There’s nothing more lovely: the warm city glow with a drink in hand while getting the lowdown on more than 50 buildings along the river. Consider it a refresher for the Chicago Architecture Biennial.

Step Three: Get to the Hamptons (Sorta)
After the cruise, walk those little sea legs over to the Hampton Social — the new River North eatery with seafood bites and coastal beach vibes. Take a look around: the whitewashed walls, the hammocks, the rocking chairs — this place is designed to transport you to the Hamptons. The food follows suit (menu’s here). Don’t sleep on the lobster Montauk Mac.