Looking for the perfect Midwest getaway? Door County, Wisconsin, offers a blend of charming towns, scenic shorelines, and a growing food and wine scene that makes it ideal for a long weekend. Whether you're planning a romantic escape, a family adventure, or a solo retreat, this 3-day itinerary will help you experience the best of Door County’s food, fun, and relaxation—all while staying in the comfort of a local vacation rental.
Day 1: Arrival & Flavors of Sturgeon Bay
Start your Door County adventure in Sturgeon Bay, the gateway to the peninsula. After checking into your vacation rental, take a leisurely walk through the historic downtown. Browse local boutiques, art galleries, and waterfront parks before heading to Door Peninsula Winery for your first wine tasting of the trip. For dinner, grab a table at a waterfront restaurant like Sonny’s Italian Kitchen, where you can enjoy lake views and wood-fired pizza. End the evening with a stroll across the Michigan Street Bridge, taking in the sunset over the bay.
Day 2: Scenic Drives & Cherry Country
After a relaxing morning, head north toward Egg Harbor and Fish Creek, two of Door County’s most beloved towns. Along the way, stop at Lautenbach’s Orchard Country for a fresh cherry pie, cider tasting, or U-pick fruit experience (in season). Spend your afternoon exploring Peninsula State Park, where hiking, biking, and breathtaking overlooks offer plenty of ways to enjoy nature. Refuel with a farm-to-table dinner in Fish Creek, then take in a live show at Peninsula Players Theatre—a local gem with performances under the stars.
Day 3: Unwind in Baileys Harbor & Sister Bay
Ease into your final day with a laid-back breakfast at a local café, then make your way to Baileys Harbor. Visit Cana Island Lighthouse for panoramic lake views and photo ops, or book a kayak tour along the shoreline for a more adventurous option. Continue to Sister Bay for an afternoon of boutique shopping, beach lounging, or even a Swedish-style lunch at Al Johnson’s, famous for the goats on its grass roof. Wrap up your trip with a relaxing evening back at your rental, maybe with a glass of wine and a front-row seat to one of Door County’s stunning sunsets.
Stay Like a Local
Choosing a Door County vacation rental instead of a hotel means more space, privacy, and the flexibility to live like a local. From cozy cabins to lakefront homes, your rental becomes the perfect home base for your Door County adventure—close to all the food, fun, and natural beauty the peninsula has to offer.
Book your Door County vacation rental today and make the most of your next long weekend escape.
