Day Trips · Southwest Michigan

The Southwest Michigan Day Trip: Wine Tasting, New Buffalo & St. Joseph

By Evan & Stina · Updated June 2026 · 6 min read

One of Valparaiso's best-kept logistical secrets: you're not just 25 minutes from the Indiana Dunes — you're also the launchpad for Harbor Country and Southwest Michigan wine country. New Buffalo is about 40 minutes up I-94; St. Joseph is about an hour. That means beach towns, lake-bluff downtowns, and a legitimate wine trail are all day-trip range — no Michigan resort-town lodging prices required.

Stop 1: New Buffalo — the Harbor Country gateway

Cross the state line and you're in New Buffalo, the little harbor town that anchors Michigan's "Harbor Country." The public beach at the marina is an easy-in, easy-out stretch of soft sand where the Galien River meets Lake Michigan — arrive in the morning for parking, swim, watch the boats head out, and grab lunch in the walkable few blocks of downtown. It's the low-effort beach morning that feels like a vacation inside a vacation.

Stop 2: wine tasting on the Lake Michigan Shore wine trail

The rolling hills behind the lakeshore are the Lake Michigan Shore AVA — one of the Midwest's most productive wine regions, with tasting rooms strung along the back roads of Berrien County. A sane afternoon is two, maybe three stops:

Prefer grain to grapes? Journeyman Distillery in the old corset factory at Three Oaks is a worthy detour for whiskey flights and a very good kitchen.

Designate a driver or book a tasting tour — the back roads are lovely and the pours are generous.

Optional stop: Warren Dunes

If the crew wants one more beach, Warren Dunes State Park in Sawyer is on the way north — a huge sandy beach below 200-foot dunes you can climb for a Lake Michigan panorama. (Michigan state parks charge an out-of-state vehicle fee; carpool and call it the wine budget.)

Stop 3: St. Joseph — the bluff-top beach town

Finish in St. Joe, the postcard of Southwest Michigan: a downtown perched on a bluff over the lake, stairs down to Silver Beach with its pier and lighthouse views, and the lovingly restored Silver Beach Carousel by the sand — the kids' highlight, guaranteed. Ice cream on the bluff, golden hour over the water, then an easy hour home down I-94.

The day at a glance

Don't forget: Michigan is on Eastern time, an hour ahead of Valparaiso — plan tasting-room closing times accordingly.

Two states, one home base

Dunes one day, Michigan wine country the next, downtown Valpo every night. Our four apartments have free parking, EV charging for the road trips, and full kitchens for the wine you'll inevitably bring home — about 10% less than booking on Airbnb.

Check availability