Our Team's Ultimate 2025 Summer Bucket List in Southwest Michigan
Looking for the best things to do in Southwest Michigan this summer? Our team at Third Coast Vacations has curated the ultimate 2025 summer bucket list, packed with local favorites and must-do experiences across Harbor Country and beyond.
Whether you're planning a beach vacation, winery weekend, or outdoor adventure, this guide features the top activities, hidden gems, and unforgettable moments we’re chasing before summer slips away. From sailing in New Buffalo to sipping craft beer in Sawyer, use this locally crafted list to plan your perfect Lake Michigan getaway.
Cruise into Summer with New Buffalo Sailing Excursions
There’s no better way to appreciate Lake Michigan than from the water. A sunset cruise with New Buffalo Sailing Excursions is top of our list—cool breezes, stunning views, and pure relaxation. Captain Steve is the best and his 6 person cruises fill up so book your quickly, we’re off to book ours now!
Soak Up Live Music at Shady Creek
Spend a day (or maybe an evening) at Shady Creek Winery in Michigan City. Great wine, beautiful views, and a rotating lineup of live music make it one of our favorite chill spots all summer long.
Eat, Drink & Lounge at River St. Joe
Farm-to-table food, organic beer brewed on-site, and wide open spaces to relax—River St. Joe in Buchanan is one of our top summer hangouts. Nestled next to Flatwater Farms, this sustainable brewery and restaurant offers more than just great eats. Kids can run and play in the open fields, live music is often on the schedule, and there’s a rotating lineup of seasonal specials, community events, and even yoga on the lawn.
Grab Pizza with a View at Silver Beach Pizza
Located inside the historic Amtrak depot just steps from Silver Beach in downtown St. Joseph, Silver Beach Pizza is a must-visit for anyone craving great food and lake views. It's always packed in the summer—and for good reason. The upstairs dining room offers front-row seats to Lake Michigan sunsets and passing trains, making it one of the most iconic spots in Southwest Michigan. We’re calling it now: The Harvest Pizza is hands-down the best thing on the menu. Get there early or be ready to wait—it’s worth it.
PADDLE THE GALIEN RIVER
If peace and quiet is what you're after, kayaking the Galien River is a dreamy way to spend a morning. Gentle currents, lush greenery, and the occasional turtle sighting? Yes, please.
Photo Credit Side yard
Catch a Show at The Dunes Summer Theatre
There's something magical about a summer night under the stars, especially when it includes a live performance at The Dunes. Check the schedule and grab tickets—this hidden gem never disappoints.
Backyard Vibes at Casey’s in New Buffalo
Nothing says summer like live music and a cold drink in hand. Head to Casey’s on a Thursday evening, grab a spot in the backyard, and soak up the energy of this beloved local hangout.
Sip a Cold One at Sideyard
This trendy new favorite in Sawyer brings beer garden vibes with a Southwest Michigan twist. With lawn games, great craft beer, and local eats nearby, Sideyard is the perfect afternoon stop.
Hike Grand Mere State Park
Towering dunes, forested trails, and lake views that make the climb worth it—Grand Mere is one of our favorite wild escapes when we need a break from the beach crowds.
Bridges + Beer = Summer Satisfaction
Lunch at Bridges in Michigan City is always a win. It’s casual, fun, and hits the spot after a long morning at the beach. Don’t skip the beer list—there’s something for everyone.
Explore (At Least) 2 New Wineries
With so many new tasting rooms popping up across Southwest Michigan, we’re making it a mission to branch out and sip somewhere new. This summer, Dablon Vineyards (known for its elegant estate reds) and Gravity Winery (hello, wine flights with a view!) are at the top of our list. Who knows—your future favorite bottle might be just around the corner, waiting to be discovered.
Take the Chikaming 10 Trail Challenge
This trail challenge is a great way to explore the natural beauty of Harbor Country while checking off some outdoor goals. Created by Chikaming Open Lands, the region’s local land conservancy, the challenge encourages you to hike 10 unique trails across Southwest Michigan—many of which are tucked-away gems even locals haven’t discovered. It’s the perfect blend of adventure, conservation, and getting outside to enjoy the landscapes we love.
Try a Goat Hike at Verdant Hollow Farms
You heard us right—goat hiking. It’s quirky, it’s fun, and it’s our top pick for a totally unique Southwest Michigan experience. Nature + goats = summer magic.
Ready to make your own summer bucket list? From sunset sails to vineyard hops, we’ve got the perfect home base for every kind of adventure. At Third Coast Vacations, we pair local expertise with exceptional vacation homes—so you can explore Southwest Michigan like a true insider.