40 days in Door County Itinerary
Created using Inspirock Door County trip itinerary planner
Start: Chicago
Fly
1
Sturgeon Bay
— 19 nights
Drive
2
Washington Island
— 20 nights
Drive
End: Chicago
Tue, Dec 15 - Sat, Jan 23
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Sturgeon Bay — 19 nights
Sturgeon Bay is a city in and the county seat of Door County, Wisconsin, United States. Explore the numerous day-trip ideas around Sturgeon Bay: Ephraim (Ephraim Historical Foundation, The Spa at Sacred Grounds, &more), Baileys Harbor (The Ridges Sanctuary, Door County Brewing Co., &more) and Fish Creek (Eagle Trail, Eagle Tower, &more). There's much more to do: stroll around Cave Point County Park, see the interesting displays at Door County Maritime Museum, immerse yourself in nature at George K. Pinney County Park, and take in nature's colorful creations at Briggsville Gardens.
To find more things to do, traveler tips, and tourist information, read Sturgeon Bay online vacation planner.
Chicago to Sturgeon Bay is an approximately 2.5-hour flight. You can also drive; or do a combination of train, bus, and car. Expect slightly colder temperatures when traveling from Chicago in December; daily highs in Sturgeon Bay reach 30°F and lows reach 19°F. Wrap up your sightseeing on the 3rd (Sun) to allow time to drive to Washington Island.
more
To find more things to do, traveler tips, and tourist information, read Sturgeon Bay online vacation planner.
Chicago to Sturgeon Bay is an approximately 2.5-hour flight. You can also drive; or do a combination of train, bus, and car. Expect slightly colder temperatures when traveling from Chicago in December; daily highs in Sturgeon Bay reach 30°F and lows reach 19°F. Wrap up your sightseeing on the 3rd (Sun) to allow time to drive to Washington Island.
Side Trips
Highlights from your trip
Washington Island — 20 nights

Washington Island is located about northeast of the tip of Door Peninsula in Door County, Wisconsin. Take a break from Washington Island with a short trip to Cast N Catch Charters in Sturgeon Bay, about 1h 50 min away. There's much more to do: don't miss a visit to Fair Isle Books & Gifts, get engrossed in the history at Jackson Harbor Maritime Museum, get great views at Mountain Park Lookout Tower, and enjoy the sand and surf at Schoolhouse Beach.
To find photos, maps, traveler tips, and more tourist information, read Washington Island road trip site.
You can drive from Sturgeon Bay to Washington Island in 2 hours. The time zone difference when traveling from Sturgeon Bay to Washington Island is 1 hour. In January, plan for daily highs up to 24°F, and evening lows to 9°F. On the 23rd (Sat), you'll travel back home.
more
To find photos, maps, traveler tips, and more tourist information, read Washington Island road trip site.
You can drive from Sturgeon Bay to Washington Island in 2 hours. The time zone difference when traveling from Sturgeon Bay to Washington Island is 1 hour. In January, plan for daily highs up to 24°F, and evening lows to 9°F. On the 23rd (Sat), you'll travel back home.
Side Trip
Highlights from your trip
Door County travel guide
Door County owes its status as a top Midwest vacation destination to its 480 km (300 mi) of shoreline along Lake Michigan. Coupled with five scenic state parks, 11 lighthouses, and 80 cultural venues, the natural scenery dominates here. The region hosts several museums, theaters, and art galleries. Art classes and workshops serve as big draws throughout the year, while live music and plays fill the entertainment schedule.