🌿 RelaxedDay trip · from Chicago, IL

Lakeside Dunes & Quiet Shores

Escape to Union Pier for a serene lakeside retreat where golden dunes meet tranquil shores, perfect for peaceful wandering and soul-refreshing solitude.

Day 1 — Union Pier

🚗 3 hr 20 min driving📍 4 stops

🌅

Morning

🚗

Drive

Chicago, IL → Union Pier

1 hr 17 min8:00 AM → 9:17 AM

Union Pier

A quiet sand-dune beach village on Lake Michigan's eastern shore with vintage cottages, a restored 1920s ice cream parlor, local wine shops, and sunset views perfect for unplugging with minimal crowds and excellent lakeside dining.

9:17 AM📍 See location

🍽️

Lunch

🍽️ Lunch10:17 AM

Brewster's New Buffalo

An Italian-influenced restaurant in New Buffalo, MI, on the southern shore of Lake Michigan — fresh pasta, good wine, and a relaxed vibe that fits the beach town perfectly.

★ 4.6Italian Restaurant📍 Maps →

2 options · tap to switch

☀️

Afternoon

🚗

Drive

Union Pier → Tabor Hill Winery & Restaurant

21 min12:00 PM → 12:21 PM

Tabor Hill Winery & Restaurant

★ 4.3

Taste award-winning wines in a sunlit tasting room overlooking vineyard rows, then linger on the terrace with a charcuterie board while Lake Michigan glimmers in the distance.

12:21 PM📍 See location

🌙

Evening

🚗

Drive

Tabor Hill Winery & Restaurant → PostBoy

27 min5:00 PM → 5:27 PM

🍽️ Dinner5:27 PM

PostBoy

This casual, upscale eatery in nearby Lakewood delivers exceptional comfort food and craft cocktails in an effortlessly sophisticated atmosphere ideal for a stress-free weekend escape.

★ 4.7Restaurant📍 Maps →

3 options · tap to switch

🚗

Drive

PostBoy → Chicago, IL

1 hr 15 min6:27 PM → 7:42 PM

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