She Goes: 24 Hours in Southwest Michigan

As we’ve grown older, we’ve learned how critical girlfriends are to our survival. When you hit your late 20s/early30s, it’s inevitable that life sometimes takes over in the form of spouses, babies, home-owning, careers and families, and friend time can often feel like a luxury rather than a necessity, which means it often falls by the wayside. For this reason, we make a point to plan a few specific events throughout the year to stay connected with our girl tribe. Early summer is the time for our annual girl’s getaway. 

This year, our destination was Southwest Michigan. This was an ideal location as it was close, easy to get to, and offered us an escape in a limited timeframe. Free weekends are hard to come by, so we opted for a Saturday-Sunday trip, and we definitely made the most of our day! 

The rundown:  

The details

We left Milwaukee around 7 a.m. on Saturday morning, properly equipped with caffeine, and headed south. Thanks to the early departure, we cruised through Chicago and, with a quick stop for gas, made it to downtown New Buffalo in a little under 3 hours. Our brunch spot. Stray Dog, didn’t open for about 30 minutes, but there was already a line forming outside, so we knew we were in a good spot. 

We took our few minutes of leisure time to stroll along the marina across the street and take in the sights of the impressive condo buildings lining the shores of Lake Michigan. It seemed we timed this trip just right. Most of the seasonal community was open for business, but it wasn’t the heart of the busy season yet. It was nice to see activity, but it didn’t feel crowded or overwhelming in any way. 

Our tummies told us it was time for lunch and, due to our well-timed arrival, we snagged a table on the rooftop deck of the Stray Dog. Within about 15 minutes, it filled up, and we get the feeling it stays that way all day. We kicked off our day with some delicious craft cocktails and homemade jalapeno poppers (WORTH IT) before tucking in to our entrees. We lingered over our food while chatting and taking in the sights of the idyllic surrounding town. Within about an hour, we all decided that another visit was likely in our future. 

After lunch, we wandered up the road. The joy of traveling with these two particular companions is that none of us is particularly bothered with planning an itinerary. We don’t mind picking a destination, departure time, and booking a spot to sleep and leaving the rest up to chance. Within three blocks, we stumbled upon our first tasting room of the day. We entered Warner Tasting Room which felt exactly like entering my grandmother’s house. It’s quaint, cozy and the lovely woman who offered us our tasting could have been anyone’s fun-loving aunt. She was sassy and chatty and we discussed the finer points of New Orleans vampire culture and the best of what’s on Netflix. A tasting that could have been done in about a half hour lasted about an hour and we were the only customers for the majority of it. It was possibly the best way to do a wine tasting at 1 pm on a Saturday when you have no schedule to keep. The price of our tasting for six pours was $7 plus tax. 

After our tasting, we opted to head to our B&B to check in and offload our vehicle. We knew more wine was in our future and didn’t want to worry about driving. This became really the only problematic part of our adventure. Initially, we wanted to check out the actual vineyards, but as it turns out, the vineyards are about 20 miles outside of all the little towns. So, we’d either have to drive and behave or find an alternative. Our first decision was to forgo the vineyards and visit the tasting rooms instead, of which there were two within two miles. The area technically has rideshare apps, but most of the drivers come from the nearest city, which in this case, was Michigan City, Indiana. We managed to snag a Lyft, but had to wait about 20 minutes for it to pick us up. (Note: per our Innkeeper, many places nearby have shuttles or other transportation options during the high season, so this may have only been an issue for this time of year). 

Luckily, the Inn at Union Pier is a B&B straight out of Gilmore Girls with its beautiful, cozy main house (complete with access to the kitchen for iced tea and cookies), a lush garden with seating and the promise of 5 p.m. wine and popcorn in the main room, so waiting for our ride was certainly no hardship.  

Eventually, we made our way to Round Barn Winery Tasting Room, which was closer to what you would expect of a winery tasting room. They obviously took a lot of their inspiration from their name and parent vineyard as wood décor and a large circular wine tasting bar were the focal points. This tasting was $12 for six pours and there were several options on their standard menu plus choices of additional seasonal items. We took our time here as well, gabbing with the wine-tenders and watching the antics of the bachelorette party next to us. It was a comfortably busy day, but everyone seemed to find a place at the bar. 

Much to our delight, the other tasting room, St. Julian’s, was directly across the street, so there were no transportation challenges to overcome with this next stop. This tasting room was less aesthetic than Round Barn, but equally as friendly and welcoming. They also had a little shop attached with snacks for purchase and wine-themed goods for sale. We loaded up on a few bottles of wine and some snacks and made our way back to our B&B. 

When we arrived back at the Inn, it was 5 p.m. and designated wine and popcorn hour. Our initial plan was to relax for a bit and then head out to dinner, but the call of a casual happy hour and a sunset over Lake Michigan were too much to resist. So, we changed into sweats, and joined two other couples in the family room. It was the best kind of vacation meeting. Happy chatter about where everyone is from, what you’re all visiting for and no pressure to linger unnecessarily. Just a happy interaction between people who are enjoying their time over a shared bottle of wine. 

With our dinner plans by the wayside, we needed to find an alternative. We searched for a place that delivers nearby and encountered only a Pizza Hut, so pizza it was. They delivered to our Inn and we made our way (pizza and Inn-provided chairs in hand) through a tree shrouded path down to the beach. The sun was just beginning to dip low in the sky and the few other beach-goers shared our relaxed vibe. There was a group enjoying a bonfire down the way, a family cuddled up on a blanket on the bluff, and the three of us, enjoying pizza and each other’s quiet company while watching the sun go down on the other side of Lake Michigan. 

Our day in Southwest Michigan was nothing short of idyllic. In a world where we often feel overwhelmed with busy-ness, it was a day to simply enjoy taking it easy. We shared great wine, great company, and no rush to do much of anything. And a day that ends with a sunset over the water is pretty much our perfect day, so we left feeling relaxed and happy and reconnected with each other. 

Where have you explored in SW Michigan and what are our must-dos on our next trip?