🌿 RelaxedDay trip · from Chicago, IL
Lakeside Dunes & Quiet Shores
Union Pier and New Buffalo are 75 minutes east on I-94 — close enough to feel effortless, different enough to feel like you've actually left. Union Pier's vintage beach cottage character predates the Harbor Country branding; it's the quieter, less-trafficked end of the strip with genuine sand-dune access. Brewster's in New Buffalo is the best Italian in the area, with fresh pasta and a crowd that knows it. Tabor Hill Winery in Buchanan, MI is the serious wine stop — one of the founding wineries of the Lake Michigan Shore AVA, producing since 1970, with a vineyard terrace that makes an afternoon disappear before the easy drive home.
Day 1 — Union Pier
Day 1 — Union Pier
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, and local wine shops. Lower foot traffic than South Haven and St. Joseph makes it the calmer Harbor Country option, with sunset views from the lakeside that face directly west over open water.
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.
2 options · tap to switch
☀️
Afternoon
🚗
Drive
Union Pier → Tabor Hill Winery & Restaurant
21 min12:00 PM → 12:21 PM
Tabor Hill Winery & Restaurant
★ 4.3Taste 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.
3 options · tap to switch
🚗
Drive
PostBoy → Chicago, IL
1 hr 15 min6:27 PM → 7:42 PM
Plan your own escapeExplore more trips →