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8-Day Family-Friendly Road and Rail Trip: Exploring Doorways Across America

Viewed by 53 travelers

Day 1: Arriving in Chicago

Chicago, USA

8:00AM

Breakfast at Lou Mitchell's

Start your journey with a hearty breakfast at the iconic Lou Mitchell's, famous for its pancakes and coffee.
Located in downtown Chicago, easily accessible prior to sightseeing.
USD15, 1 hour

9:30AM

Explore Millennium Park

Stroll through Millennium Park and take pictures at the stunning Cloud Gate sculpture, also known as 'The Bean'.
Just a short walk from breakfast, approximately 0.5 miles.
Free, 2 hours

12:00PM

Lunch at Giordano's

Enjoy a famous deep-dish pizza at Giordano's, a well-loved Chicago staple that kids will enjoy.
A short drive from Millennium Park, around 1.5 miles.
USD30, 1.5 hours

2:00PM

Tour the Chicago Architecture Center

Discover the 'doors' of Chicago through an architectural boat tour along the river, providing insights into the city's famous buildings.
About a 10-minute drive from lunch.
USD45, 2 hours

5:00PM

Drive to Milwaukee

After a fun day in Chicago, set off on a scenic drive to Milwaukee, known for its beautiful lakeside views.
Approx. 90 miles north, about an hour and a half drive.
USD20 (gas), 1.5 hours

7:00PM

Dinner at SafeHouse

Dine at the spy-themed SafeHouse restaurant, fun and family-friendly with secret doors and interactive dining.
Located in downtown Milwaukee, an easy drive from your hotel.
USD50, 1.5 hours
Find Hotels in Chicago

Day 2: Milwaukee Adventures

Milwaukee, USA

8:00AM

Breakfast at Milwaukee Ale House

Savour morning brews and hearty breakfast plates with a view of the river at Milwaukee Ale House.
A short walk along the riverfront, about 0.3 miles.
USD25, 1 hour

9:30AM

Visit the Milwaukee Art Museum

Admire the architectural marvel of the museum, with iconic outdoor sculptures and its notable folding wings.
Approximately 1 mile from breakfast.
USD15, 2 hours

12:00PM

Lunch at The Commons

Enjoy a family-friendly lunch with various styles and healthy options that appeal to all tastes.
A short drive of about 0.5 miles.
USD40, 1 hour

1:30PM

Explore Harley-Davidson Museum

Immerse yourselves in the history of the iconic motorcycle brand while checking out vintage bikes and memorabilia.
Only 1 mile away, an easy drive or short walk.
USD20, 2 hours

4:00PM

Drive to Madison

Travel to Madison, Wisconsin, the state capital known for its beautiful parks and lakes.
About 80 miles west, around 1.5 hours drive.
USD15 (gas), 1.5 hours

6:30PM

Dinner at The Old Fashioned

A classic Wisconsin supper club experience with iconic local dishes to satisfy every family member.
Located near the state capitol on the isthmus.
USD60, 1.5 hours
Find Hotels in Milwaukee

Day 3: Exploring Madison

Madison, USA

8:00AM

Breakfast at Marigold Kitchen

Start your day with a wholesome breakfast dish crafted from local ingredients in this cozy eatery.
About 1 mile from your accommodation.
USD20, 1 hour

9:30AM

Visit Wisconsin State Capitol

Tour the stunning state capitol building, with magnificent domed architecture and historical exhibits.
A short 0.5-mile drive from breakfast.
Free, 1.5 hours

11:00AM

Explore the Madison Children’s Museum

Engage in hands-on exhibits that allow your kids to learn through play in a fun and friendly environment.
About 1 mile west of the capitol.
USD15, 2 hours

1:00PM

Lunch at The Great Dane Pub & Brewing Co.

Refuel with a delicious pub lunch featuring house-brewed beer for the adults and kid-friendly options.
1 mile from the museum.
USD40, 1 hour

2:30PM

Biking around Lake Monona

Rent bikes and enjoy a scenic ride along the lake, discovering beautiful parks and views.
Nearby rental shops available downtown.
USD40, 2 hours

5:00PM

Drive to Green Bay

Set off for Green Bay, famous for its sports teams and vibrant community.
Approximately 120 miles northeast, about 2 hours drive.
USD20 (gas), 2 hours

7:30PM

Dinner at The Olive Garden

Complete your day with an Italian feast at Olive Garden, beloved by families for its tasty pasta and unlimited breadsticks.
A quick drive within Green Bay.
USD50, 1.5 hours
Find Hotels in Madison

Day 4: Green Bay Highlights

Green Bay, USA

9:00AM

Breakfast at The Pancake Place

Delight in a variety of pancakes and omelettes in a warm family-friendly atmosphere.
About 2 miles from the hotel.
USD20, 1 hour

10:30AM

Visit the Green Bay Packers Hall of Fame

Learn all about the storied history of the Green Bay Packers at this must-see attraction for sports enthusiasts.
1 mile drive from breakfast.
USD25, 1.5 hours

12:30PM

Lunch at Kroll's West

Savour a classic cheeseburger or their famous butter burgers at this beloved diner.
Approximately 1 mile from the Hall of Fame.
USD30, 1 hour

2:00PM

Explore the National Railroad Museum

Discover the historic locomotives and cars that showcase the region's rich railway history.
1 mile from Kroll's West.
USD20, 2 hours

4:30PM

Drive to Door County

Transition to picturesque Door County, known for its charming towns and stunning landscapes.
About 60 miles northeast, approximately 1.5 hours.
USD15 (gas), 1.5 hours

6:30PM

Dinner at The White Gull Inn

Enjoy a cosy dinner of local fish and comfort food, complete with views of the lush surroundings.
Located in Fish Creek, a charming town in Door County.
USD65, 1.5 hours
Find Hotels in Green Bay

Day 5: Exploring Door County

Door County, USA

8:00AM

Breakfast at Al Johnson's Swedish Restaurant

Experience a fun Swedish breakfast while also watching goats grazing on the green roof!
Located in Sister Bay, about a 20-minute drive.
USD30, 1.5 hours

10:00AM

Visit Peninsula State Park

Explore the park’s scenic trails and lookout points, offering beautiful views of the water and lighthouse.
A short 15-minute drive from breakfast.
USD10 (parking), 3 hours

1:00PM

Lunch at Wilson's Restaurant

Make your way to historic Wilson's for ice cream and a retro-style lunch right by the marina.
Just a 10-minute drive away.
USD40, 1.5 hours

3:00PM

Explore Egg Harbor

Discover the charming shops and accessible waterfront in idyllic Egg Harbor.
A short 15-minute drive south.
Free, 2 hours

5:30PM

Drive to Washington Island

Catch a ferry across to Washington Island, known for its serene beauty and outdoor adventures.
About 30 minutes drive to the ferry terminal, then a short ferry ride.
USD50 (ferry), 1.5 hours

7:00PM

Dinner at The Tavern

Enjoy a hearty seafood feast at this locals-favourite restaurant with a family-friendly vibe.
Located walking distance from the ferry landing.
USD60, 1.5 hours
Find Hotels in Door County

Day 6: Exploring Washington Island

Washington Island, USA

8:00AM

Breakfast at Nelsen's Hall

Start your day with a delightful breakfast in this charming hall that offers local specialties.
A short walk from your accommodation.
USD20, 1 hour

9:30AM

Visit the Washington Island Farm

Enjoy petting goats and learning about farming life while the kids enjoy the open spaces.
Just 10 minutes drive from breakfast.
Free, 1.5 hours

11:00AM

Explore the island’s beautiful beaches

Windy, sandy shores perfect for a family beach day while collecting seashells and enjoying the scenery.
A short drive or bike ride around the island.
Free, 2.5 hours

1:30PM

Pack a picnic lunch

Grab some local produce from the farm market and have an informal lunch at the beach.
Plan on visiting local markets to stock up.
USD25, 1 hour

2:30PM

Visit the Island Lighthouse

Tour the historic lighthouse providing stunning views and a glimpse into maritime history.
Easily accessible by driving around the island.
USD10, 1.5 hours

4:30PM

Ferry back to Door County

Head back across the water, filled with memories of the vibrant island.
Catch the ferry from the same terminal as before.
USD50 (ferry), 1 hour

6:00PM

Dinner at Wild Tomato

Savour gourmet pizzas in a relaxed setting, perfect after a day of exploring.
Located in Fish Creek just off the main highway.
USD45, 1.5 hours
Find Hotels in Washington Island

Day 7: Bayfield Bound

Bayfield, USA

8:00AM

Breakfast at The Cookery

Enjoy a homey breakfast of smoked fish and farm-fresh ingredients in this charming eatery.
About a 20-minute drive from Fish Creek.
USD25, 1 hour

10:00AM

Drive to Bayfield

Head to the quaint town of Bayfield, known for its apple orchards and lakeside fun.
Approximately 75 miles northwest, a road trip of 1.5 hours.
USD20 (gas), 1.5 hours

12:00PM

Lunch at Bayfield Apple Company

Taste local apple brats and seasonal treats while peering into the orchard views.
Located in town, easy access.
USD30, 1 hour

1:30PM

Explore Apostle Islands National Lakeshore

Take in breathtaking views, hiking trails and perhaps spot a lighthouse on the shores of Lake Superior.
About 15 minutes drive from lunch.
USD10 (parking), 2.5 hours

4:30PM

Return to Bayfield for some shopping

Explore local shops featuring handmade crafts and treats before dinner.
Short drive back into town.
Free, 1.5 hours

6:30PM

Dinner at The Bayfield Inn

Enjoy vibrant dishes with magnificent views of the sunset over the lake.
Walking distance from your shopping spree in town.
USD60, 1.5 hours
Find Hotels in Bayfield

Day 8: Final Stop – Duluth

Duluth, USA

8:00AM

Breakfast at The Duluth Grill

Indulge in a locally sourced breakfast to kickstart your final day of adventure.
Short drive, around 1 mile from your accommodation.
USD25, 1 hour

9:30AM

Visit the Richard I. Bong Veterans Historical Center

Learn about historical events and the stories that shaped the nation in this engaging museum.
A short drive of about 2 miles.
USD10, 2 hours

12:00PM

Lunch at Grandma’s Saloon & Grill

Treat yourself to a hearty lunch in a relaxed setting with classic American fare.
Located in Canal Park, about a mile from the museum.
USD45, 1.5 hours

2:00PM

Explore Canal Park

Enjoy waterfront views, shops, and the iconic Aerial Lift Bridge, perfect for a family photo.
A short walk down the street.
Free, 2 hours

4:30PM

Visit Glensheen Historic Estate

Explore the stunning mansion by the lake with beautiful grounds and fascinating history.
Easily accessible via the lakeside drive.
USD20, 2 hours

7:00PM

Dinner at Lake Avenue Restaurant

Enjoy the final meal of your trip with fresh local cuisine while overlooking the waterfront.
Located nearby for a perfect end to your journey.
USD70, 1.5 hours
Find Hotels in Duluth
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