10 days in Wisconsin, Chicago & Nashville Itinerary

10 days in Wisconsin, Chicago & Nashville Itinerary

Created using Inspirock United States Trip Planner

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Route & dates

Start: Toronto
Fly + Drive:  10 h 15 min
1
Sister Bay
— 2 nights
Drive:  3 h 45 min
2
Wisconsin Dells
— 2 nights
Drive:  1 h 15 min
3
Madison
— 2 nights
Drive:  2 h 45 min
4
Chicago
— 1 night
Fly + Bus:  3 h 45 min
5
Nashville
— 2 nights
Fly:  9 h 30 min
End: Toronto

2
nights
Sister Bay

Sister Bay ©
Sister Bay is a village in Door County, Wisconsin, United States. Start off your visit on the 19th (Sun): stop by Wood Orchard, then walk around Cave Point County Park, and then immerse yourself in nature at Peninsula State Park. Get ready for a full day of sightseeing on the 20th (Mon): enjoy the sea views from Cana Island Lighthouse and then stroll around Waterfront Park.

To find traveler tips, maps, where to stay, and other tourist information, refer to the Sister Bay trip itinerary maker website.

Toronto, Canada to Sister Bay is an approximately 9- hour combination of flight and car. You can also drive. Traveling from Toronto to Sister Bay, you'll gain 1 hour due to the time zone difference. Traveling from Toronto in August, you can expect nighttime temperatures to be a bit cooler in Sister Bay, with lows of 15°C. Finish your sightseeing early on the 21st (Tue) to allow enough time to travel to Wisconsin Dells.

Things to do in Sister Bay

Parks Nature Historic Sites

Side Trips

Cave Point County Park, Wood Orchard, Peninsula State Park, Cana Island Lighthouse
Find places to stay Aug 19 — 21:
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Peninsula State Park ©
Peninsula State Park
Cana Island Lighthouse ©
Cana Island Lighthouse
Wood Orchard ©
Wood Orchard

2
nights
Wisconsin Dells

Wisconsin Dells ©
Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
On the 21st (Tue), identify plant and animal life at International Crane Foundation and then admire the landmark architecture of Taliesin Preservation: Frank Lloyd Wright Visitor Center . On your second day here, stroll around Wisconsin Deer Park, then have some family-friendly fun at Laser Warfare, and then admire the majestic nature at Devil's Lake State Park.

To find where to stay, photos, reviews, and tourist information, use the Wisconsin Dells online driving holiday planner.

Traveling by car from Sister Bay to Wisconsin Dells takes 4 hours. In August, daily temperatures in Wisconsin Dells can reach 30°C, while at night they dip to 17°C. On the 23rd (Thu), wrap the sightseeing up by early afternoon so you can drive to Madison.

Things to do in Wisconsin Dells

Parks Outdoors Zoos & Aquariums

Side Trips

Baraboo, Taliesin Preservation: Frank Lloyd Wright Visitor Center
Find places to stay Aug 21 — 23:
Highlights from your plan
Wisconsin Deer Park ©
Wisconsin Deer Park
International Crane Foundation ©
International Crane Foundation

2
nights
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
On the 24th (Fri), learn about wildlife with up-close encounters at Henry Vilas Zoo, then take in nature's colorful creations at Olbrich Botanical Gardens, and then ponder the world of politics at Wisconsin State Capitol. On the next day, sample the tasty concoctions at New Glarus Brewing Company and then sample the fine beverages at Wollersheim Winery & Distillery.

For photos, maps, reviews, and other tourist information, read Madison trip builder app.

Traveling by car from Wisconsin Dells to Madison takes 1.5 hours. Alternatively, you can do a combination of train and bus. In August, daytime highs in Madison are 31°C, while nighttime lows are 18°C. Finish your sightseeing early on the 25th (Sat) to allow enough time to drive to Chicago.

Things to do in Madison

Parks Breweries & Distilleries Zoos & Aquariums

Side Trips

New Glarus Brewing Company, Wollersheim Winery & Distillery
Find places to stay Aug 23 — 25:
Highlights from your plan
Wollersheim Winery & Distillery ©
Wollersheim Winery & Distillery
New Glarus Brewing Company ©
New Glarus Brewing Company
Olbrich Botanical Gardens ©
Olbrich Botanical Gardens

1
night
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 26th (Sun): don't miss a visit to Buckingham Fountain and then learn the secrets of beer at a beer tour and tasting.

To see other places to visit, ratings, maps, and tourist information, go to the Chicago road trip site.

Drive from Madison to Chicago in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Madison in August, expect a bit warmer with lows of 22°C in Chicago. Wrap up your sightseeing by early afternoon on the 26th (Sun) to allow time for travel to Nashville.

Things to do in Chicago

Tours
Find places to stay Aug 25 — 26:
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Beer Tastings & Tours
Buckingham Fountain ©
Buckingham Fountain

2
nights
Nashville

Nashville ©
Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Start off your visit on the 27th (Mon): witness the site of a historic battle at Carnton, then take in the history at Carter House, and then appreciate the extensive heritage of Downtown Franklin.

To see more things to do, other places to visit, photos, and more tourist information, go to the Nashville road trip planning app.

You can do a combination of flight and bus from Chicago to Nashville in 4 hours. Alternatively, you can do a combination of subway, bus, and flight; or drive. Traveling from Chicago in August, expect nights in Nashville to be about the same, around 24°C, while days are a bit warmer, around 37°C. On the 28th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Nashville

Historic Sites Museums Neighborhoods

Side Trip

Franklin
Find places to stay Aug 26 — 28:
Highlights from your plan
Downtown Franklin ©
Downtown Franklin
Carter House ©
Carter House
Hatch Show Print ©
Hatch Show Print

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