37 days in Wisconsin & San Diego Itinerary

37 days in Wisconsin & San Diego Itinerary

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Route & dates

37 days in Wisconsin & San Diego Itinerary

Start: Chicago
Drive:  2​h 45​min
1
Madison
— 3 nights
Drive:  1​h 15​min
2
Wisconsin Dells
— 3 nights
Drive:  2​h 15​min
3
Chippewa Falls
— 4 nights
Drive:  3​h
4
Bayfield
— 2 nights
Drive:  2​h 15​min
5
Minocqua
— 3 nights
Drive:  1​h 15​min
6
Wausau
— 3 nights
Drive:  1​h 45​min
7
Green Bay
— 4 nights
Drive:  1​h 15​min
8
Sheboygan
— 3 nights
Drive:  1​h
9
Milwaukee
— 4 nights
Fly:  5​h 45​min
10
San Diego
— 7 nights
Fly:  6​h 15​min
End: Chicago

3
nights
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Change things up with these side-trips from Madison: Lake Mills (Ephraim Pottery & Lewis Station Winery), Dwight Foster Public Library (in Fort Atkinson) and Rotary Botanical Gardens (in Janesville). And it doesn't end there: take in nature's colorful creations at Olbrich Botanical Gardens, see the interesting displays at Matt Kenseth Racing Museum, see the sights as you ascend with a climbing tour, and make a trip to Memorial Union Terrace.

To see photos, maps, more things to do, and other tourist information, you can read our Madison online day trip planner .

Chicago to Madison is an approximately 3-hour car ride. You can also take a bus; or do a combination of train and bus. Expect slightly colder temperatures when traveling from Chicago in December; daily highs in Madison reach 32°F and lows reach 19°F. Finish your sightseeing early on the 13th (Fri) to allow enough time to drive to Wisconsin Dells.

Things to do in Madison

Parks Outdoors Tours

Side Trips

Lake Mills, Matt Kenseth Racing Museum, Pheasant Branch Creek Conservancy, Dwight Foster Public Library, Rotary Botanical Gardens
Highlights from your plan
Rotary Botanical Gardens ©
Rotary Botanical Gardens
Olbrich Botanical Gardens ©
Olbrich Botanical Gardens

3
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.
Step out of Wisconsin Dells to go to Westby and see Snowflake Ski Club, which is approximately 1h 20 min away. Next up on the itinerary: have some family-friendly fun at Elusive Escape Rooms, see the interesting displays at Mr. Marvel's Wondertorium, hit the slopes at Cascade Mountain, and engage your brain at Flyways Waterfowl Experience.

To see maps, more things to do, reviews, and more tourist information, you can read our Wisconsin Dells day trip planner.

You can drive from Madison to Wisconsin Dells in 1.5 hours. Another option is to do a combination of bus and train. In December, plan for daily highs up to 30°F, and evening lows to 18°F. Finish your sightseeing early on the 16th (Mon) so you can travel to Chippewa Falls.

Things to do in Wisconsin Dells

Parks Winter Sports Outdoors

Side Trips

Baraboo, Portage, Snowflake Ski Club
Highlights from your plan
Elusive Escape Rooms ©
Elusive Escape Rooms
Flyways Waterfowl Experience ©
Flyways Waterfowl Experience
Cascade Mountain ©
Cascade Mountain

4
nights
Chippewa Falls

Chippewa Falls ©
Chippewa Falls is a city located on the Chippewa River in Chippewa County in the U.S. Venture out of the city with trips to The Highground Veterans Memorial Park (in Neillsville), La Crosse (Riverside Museum, Room Escape Games, & more) and Alma (Lock and Dam 4 & Buena Vista Park). There's still lots to do: delve into the lush surroundings at Tower Ridge Recreational Area, get engrossed in the history at Chippewa Valley Museum, sample the fine beverages at Perlick Distillery, and stop by Chippewa Candy Shop.

To find other places to visit, maps, and more tourist information, you can read our Chippewa Falls travel route planner .

Traveling by car from Wisconsin Dells to Chippewa Falls takes 2.5 hours. In December, daytime highs in Chippewa Falls are 27°F, while nighttime lows are 14°F. Finish your sightseeing early on the 20th (Fri) so you can travel to Bayfield.

Things to do in Chippewa Falls

Parks Museums Trails

Side Trips

La Crosse, Alma, Eau Claire, Pioneer Village Museum, Wisconsin Canoe Heritage Museum
Highlights from your plan
Buena Vista Park ©
Buena Vista Park
Tower Ridge Recreational Area ©
Tower Ridge Recreational Area
Lock and Dam 4 ©
Lock and Dam 4

2
nights
Bayfield

Bayfield ©
Bayfield is a city in Bayfield County, Wisconsin, United States. On the 21st (Sat), get engrossed in the history at Bayfield Maritime Museum, glide through natural beauty at Pike's Creek Mt Ashwabay Ski Trails, then stop by Madeline Island Candles, and finally explore the fascinating underground world of Apostle Islands National Lakeshore Ice Caves. Keep things going the next day: shop like a local with Stone's Throw Art Gallery, indulge in some personalized pampering at some of the best spas, then admire the majestic nature at Copper Falls State Park, and finally steep yourself in history at Soo Line 950.

To find maps, ratings, and other tourist information, you can read our Bayfield sightseeing planning tool .

You can drive from Chippewa Falls to Bayfield in 3 hours. Expect a daytime high around 25°F in December, and nighttime lows around 13°F. Cap off your sightseeing on the 22nd (Sun) early enough to travel to Minocqua.

Things to do in Bayfield

Parks Nature Shopping

Side Trips

Madeline Island Candles, Soo Line 950, Copper Falls State Park
Highlights from your plan
Copper Falls State Park ©
Copper Falls State Park
Madeline Island Candles ©
Madeline Island Candles

3
nights
Minocqua

Minocqua ©
Minocqua is a town in northwestern Oneida County, Wisconsin, United States. You'll find plenty of places to visit near Minocqua: Eagle River (Eagle River Historical Museum & Northwoods Children's Museum), WinMan Trails (in Winchester) and Kovac Planetarium (in Rhinelander). The adventure continues: glide through natural beauty at Minocqua Winter Park, sample the tasty concoctions at Rocky Reef Brewing Company, get engrossed in the history at Vilas County Historical Museum, and brush up on your knowledge of spirits at Northern Waters Distillery.

For maps, traveler tips, ratings, and more tourist information, use the Minocqua trip itinerary builder site .

You can drive from Bayfield to Minocqua in 2.5 hours. Expect a daytime high around 25°F in December, and nighttime lows around 13°F. Wrap up your sightseeing on the 25th (Wed) early enough to drive to Wausau.

Things to do in Minocqua

Museums Winter Sports Parks

Side Trips

Eagle River, Ojibwe Museum & Cultural Center, WinMan Trails, Kovac Planetarium, Vilas County Historical Museum
Highlights from your plan
Vilas County Historical Museum ©
Vilas County Historical Museum
WinMan Trails ©
WinMan Trails
Minocqua Winter Park ©
Minocqua Winter Park

3
nights
Wausau

Wausau ©
Wausau is a city in and the county seat of Marathon County, Wisconsin, United States. Explore Wausau's surroundings by going to Stevens Point (Central Wisconsin Children's Museum & Green Circle Trail), 45 x 90 Geographical Marker (in Athens) and Nueske's (in Wittenberg). There's still lots to do: explore the world behind art at Leigh Yawkey Woodson Art Museum, sample the tasty concoctions at Bull Falls Brewery, see the interesting displays at Woodson History Center, and stop by Mullins Cheese.

To see other places to visit, maps, photos, and tourist information, you can read our Wausau trip itinerary builder app .

You can drive from Minocqua to Wausau in 1.5 hours. December in Wausau sees daily highs of 26°F and lows of 14°F at night. Wrap up your sightseeing on the 28th (Sat) early enough to travel to Green Bay.

Things to do in Wausau

Museums Parks Breweries & Distilleries

Side Trips

Stevens Point, 45 x 90 Geographical Marker, Mullins Cheese, Nueske's, Sawmill Brewing Company
Highlights from your plan
Leigh Yawkey Woodson Art Museum ©
Leigh Yawkey Woodson Art Museum
Woodson History Center ©
Woodson History Center
Lil' Ole Winemaker Shoppe ©
Lil' Ole Winemaker Shoppe

4
nights
Green Bay

Green Bay ©
Home of the Green Bay Packers, the city of Green Bay centers around sports and is home to hundreds of notable football icons, including Brett Favre and Curly Lambeau.
You'll find plenty of places to visit near Green Bay: R. Harder Gallery of Gems and Minerals (in Neenah), Sturgeon Bay (The Farm, Cave Point County Park, & more) and Fish Creek (Edgewood Orchard Galleries & Peninsula State Park). There's much more to do: examine the collection at Green Bay Packer Hall of Fame, admire the natural beauty at Green Bay Botanical Garden, admire the masterpieces at Paine Art Center and Gardens, and make a trip to George Burr Gallery.

To find where to stay, maps, traveler tips, and tourist information, you can read our Green Bay journey planning site .

Traveling by car from Wausau to Green Bay takes 2 hours. December in Green Bay sees daily highs of 31°F and lows of 18°F at night. Finish your sightseeing early on the 1st (Wed) so you can drive to Sheboygan.

Things to do in Green Bay

Museums Parks Shopping

Side Trips

Sturgeon Bay, Fish Creek, Oshkosh, R. Harder Gallery of Gems and Minerals, Shrine of Our Lady of Good Help
Highlights from your plan
Green Bay Packer Hall of Fame ©
Green Bay Packer Hall of Fame
Green Bay Botanical Garden ©
Green Bay Botanical Garden
EAA Aviation Museum ©
EAA Aviation Museum

3
nights
Sheboygan

Sheboygan ©
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. You'll find plenty of places to visit near Sheboygan: Shalom Wildlife Zoo (in West Bend), Horicon Marsh (in Mayville) and Belgium (Luxembourg American Cultural Society & Cedar Valley Cheese). Next up on the itinerary: take in nature's colorful creations at Bookworm Gardens, indulge your thirst for a good beer at 3 Sheeps Brewing Company, make a trip to Walldogs, and play a few rounds at Whistling Straits Golf Course - Straits and Irish.

For maps, photos, ratings, and tourist information, go to the Sheboygan trip tool .

Getting from Green Bay to Sheboygan by car takes about 1.5 hours. In January in Sheboygan, expect temperatures between 26°F during the day and 12°F at night. Finish your sightseeing early on the 4th (Sat) so you can drive to Milwaukee.

Things to do in Sheboygan

Parks Museums Zoos & Aquariums

Side Trips

Belgium, Road America, Whistling Straits Golf Course - Straits and Irish, Shalom Wildlife Zoo, Horicon Marsh
Highlights from your plan
Bookworm Gardens ©
Bookworm Gardens
Shalom Wildlife Zoo ©
Shalom Wildlife Zoo
Horicon Marsh ©
Horicon Marsh

4
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Explore Milwaukee's surroundings by going to SC Johnson Headquarters (in Racine), Horicon Marsh Explorium (in Horicon) and Veterans Memorial Park (in Oconomowoc). Next up on the itinerary: take in the spiritual surroundings of Basilica of St. Josaphat, see the interesting displays at Harley-Davidson Museum, sample the tasty concoctions at Lakefront Brewery, and admire the masterpieces at Milwaukee Art Museum.

To see photos, ratings, other places to visit, and more tourist information, you can read our Milwaukee planner .

You can drive from Sheboygan to Milwaukee in an hour. In January in Milwaukee, expect temperatures between 30°F during the day and 16°F at night. Finish your sightseeing early on the 8th (Wed) to allow enough time to travel to San Diego.

Things to do in Milwaukee

Museums Historic Sites Parks

Side Trips

Lake Geneva, Cedarburg, SC Johnson Headquarters, Veterans Memorial Park, Vines to Cellars Winery
Highlights from your plan
Chudnow Museum of Yesteryear ©
Chudnow Museum of Yesteryear
Basilica of St. Josaphat ©
Basilica of St. Josaphat
SC Johnson Headquarters ©
SC Johnson Headquarters

7
nights
San Diego

San Diego ©
Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Explore the numerous day-trip ideas around San Diego: Self Realization Fellowship Hermitage & Meditation Gardens (in Encinitas), Disney California Adventure Park (in Anaheim) and Lions, Tigers & Bears (in Alpine). And it doesn't end there: get to know the resident critters at San Diego Zoo, see the interesting displays at Maritime Museum of San Diego, enjoy the sand and surf at La Jolla Cove, and pause for some photo ops at Cabrillo National Monument.

For other places to visit, ratings, maps, and other tourist information, you can read our San Diego holiday planner.

Traveling by flight from Milwaukee to San Diego takes 6 hours. Alternatively, you can do a combination of bus and flight; or drive. You'll gain 2 hours traveling from Milwaukee to San Diego due to the time zone difference. Traveling from Milwaukee in January, things will get much warmer in San Diego: highs are around 67°F and lows about 51°F. Wrap up your sightseeing by early afternoon on the 15th (Wed) to allow enough time to travel back home.

Things to do in San Diego

Parks Theme Parks Zoos & Aquariums

Side Trips

Self Realization Fellowship Hermitage & Meditation Gardens, Disney California Adventure Park, Lions, Tigers & Bears
Highlights from your plan
San Diego Zoo ©
San Diego Zoo
USS Midway Museum ©
USS Midway Museum
Balboa Park ©
Balboa Park

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