Door County is an easy weekend or week trip if you live in Chicago or Wisconsin. If you aren’t located close, you can fly into Chicago or Milwaukee. We just did 48 hours and it was perfect. I’m handing you the exact itinerary so you don’t have to figure it out yourself. Save this one, you’ll want it later.
Arrival day:
We checked into our adorable cottage and were immediately obsessed. Then we rolled into Fish Creek in the late afternoon and headed straight to the cute little market in town to grab groceries for a simple backyard dinner. No reservations, no rush — just settling in, letting the kids run around, and cooking something easy while we watched the sun go down. This is the move we usual do: we don’t plan anything big for arrival night.
Day 1: Bikes, Beaches, and Yummy Pizza
We rented bikes and biked through Peninsula State Park — genuinely one of my favorite things we’ve ever done as a family. Stop at the lighthouse, then land at Nicolet Beach for a swim break. Pro tip: Nicolet Beach has a food truck, a little store, a changing station, bathrooms, and even showers, so you can spend the day there. We were renting our bikes, so we only stayed an hour.
From there, we grabbed a late-afternoon sandwich and ice cream at the Creamery in Sister Bay (this is a MUST in Door County), then headed back to the cottage to relax in the sunroom before dinner — because a 48-hour trip still needs a slow moment built in.
For dinner, we drove to Baileys Harbor for Inland Sourdough Pizza and it was SO good. I’m already thinking about it. We ran out of time to hit Sway Brewery right nearby, and Baileys Harbor also has Chive and the Chive food truck — both on our list for next time.
A few extra notes for your back pocket: if you’ve got kids, there’s no shortage of mini golf — Pirate’s Cove and Evergreen (which has glow-in-the-dark mini golf, a total hit) are both nearby. And Not Licked custard is a certified family favorite — don’t skip it.
Day 2: A Quick Trip to Washington Island
Here’s my honest hot take: there isn’t a ton to actually do on Washington Island, but I’m still glad we went.
We started with breakfast at KK Fiske Restaurant, Granary Saloon & Coop hangout — very local, great food, and shockingly cheap. We were drawn there because my step-brother and step-sister (yes, the Top Chef ones) did a residency at Hotel Washington, and this happened to be their last week before heading to Maine. Coming to see them gave us the perfect excuse to explore the island.
The two must-do’s: Schoolhouse Beach and the lavender farm. We also drove past the clock tower (so random, in the best way) and climbed the mountain tower for the view. Beyond that, there’s a lot of time to kill — it was still fun to cruise around and look at the houses, but I wouldn’t recommend spending a full day here.
My real advice: go for breakfast, the beach, and the lavender farm, then take the ferry back. If you don’t have kids along, the Bitters Bar is worth a look — it’s the oldest bitters bar around with a lot of history, but it’s a dive, so we skipped it with our crew this time. And if you’re there for dinner, I hope the next chef lives up to Jennifer and Justin — honestly, I doubt it.
Then it’s back on the ferry and back to Fish Creek for one more night at the cottage.
One Last Stop on Your Way Out
Before we left Door County, we swung by Cultured for bagels — amazing, don’t skip it — and made a stop at Cave Point. It is genuinely so pretty and an absolute must-visit if you’re heading out of the peninsula. Build in the extra 20 minutes, you won’t regret it.
Where We Stayed: The Cherry Cottages
We stayed at The Cherry Cottages in Fish Creek and it made the whole trip work. Two bedrooms that including bunks for the kids, a great backyard, a huge and brand-new kitchen, and — the actual best part — a sunroom I never wanted to leave. The location puts you right close to everything including the adorable Fish Creek.
If you book direct, use code CHERRY15 to save 15%. I’ll share photos of the space so you can see exactly what I mean. It’s the perfect size for a family of 4 or 5 (the couch turns into a sofa bed!)
Door County in 48 hours is completely doable, and honestly prefect for a family getaway. Save this post, send it to a friend, and go book your trip.
The Traveling Tinsleys 