Ready to ditch the city for a bit and trade skyscrapers for shoreline? Let’s talk about one of the most charming escapes from Chicago — Door County, Wisconsin — and why exploring it in a Jeep is the best move you’ll make this season.

This Midwest gem, just about a 4-hour scenic drive from the Windy City, is packed with jaw-dropping lake views, cozy lighthouses, cherry orchards, and roadside pie stands that’ll change your life. And nothing beats cruising through the twists and turns of Door County's peninsulas with the top down and the breeze in your hair. Let's map out your adventure, Jeep-style.

First Stop: Hit the Road with Confidence

Before we even talk about lighthouses and fish boils, let’s talk about wheels. Chicago Adventure Rentals hooks you up with rugged, trail-ready Jeeps that practically beg to be driven off the beaten path. Located conveniently in Lakeview, just off Broadway and Addison, this rental spot is known for its killer customer service, well-maintained rides, and the freedom to explore wherever the road (or dirt trail) takes you.

🌲 Itinerary Day 1: Cruise Into Sturgeon Bay

🕐 Drive time: ~4 hours
🎯 Must-do:

• Stop at Renard’s Cheese near Sturgeon Bay for fresh cheese curds

• Cruise the Bay Shore Drive Scenic Byway for unbeatable lake views

• Dinner at Sonny’s Pizzeria, right by the water

📸 Pro tip: Take your Jeep top down and catch the wind on County Road B—it’s a Midwest vibe you didn’t know you needed.

🏞️ Day 2: Nature Day – Cave Point & Whitefish Dunes

Get ready to get your boots dirty and your soul refreshed. Door County is stacked with natural gems:

🌊 Cave Point County Park

• Dramatic limestone cliffs

• Crystal-clear waters (perfect for pics)

• You can even kayak through sea caves if you're feeling bold

🌲 Whitefish Dunes State Park

• Sandy beaches + forest hikes = best of both worlds

• Less crowded than Peninsula State Park (local secret!)

💡 Highlight: Jeeps are perfect for the gravel roads leading to tucked-away trailheads.

🍒 Day 3: Peninsula Pit Stops & Lighthouse Views

Take the long way up the peninsula with these iconic detours:

• Fish Creek: Shop local boutiques, grab a coffee at Blue Horse Beach Café

• Eagle Bluff Lighthouse: Epic views + cool history = win-win

• Sister Bay: End the day with dinner at Al Johnson’s Swedish Restaurant, where goats hang out on the roof (yes, really 🐐)

🔦 Don’t skip a quick hike at Peninsula State Park—you’ll catch some of the best panoramic lake views in the Midwest.

🎣 Bonus: Fish Boil & Sunset Drive

Wrap your trip with a classic Door County fish boil at Rowleys Bay Resort—it’s smoky, rustic, and oh-so Wisconsin. After dinner, take County Highway Q for a golden-hour Jeep cruise you’ll never forget.

🕶️ Quick Packing List

• Sunglasses

• Hiking boots

• Phone charger (and car mount!)

• Snacks for the drive

• A chill playlist 🎶

🧭 Ready to Roll?

Door County’s got the charm. The Jeep’s got the muscle. And all you need is the right set of keys to unlock it all. Chicago Adventure Rentals has you covered with flexible bookings, unbeatable ride quality, and friendly folks ready to make your trip actually stress-free.

Book your adventure-ready Jeep today by visiting us 👉 here or giving us a call at 📞 +1 872-296-8008. Let's get you road trip ready—Door County’s calling!