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By Huuk Team

Road trip from Jacksonville to Milwaukee

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ITINERARY

21h 32m1,146 miles16 stops
1
Rogers Farm
3831 NW 156th Ave, Gainesville, FL 32609-5028
2
Underbelly
113 E Bay St, Jacksonville, FL 32202-3414
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
3
Rockin N Stables
5178 Mount Olive Rd, Tallahassee, FL
We offer trail rides, riding lessons, birthday parties and summer camps. If you love horseback riding, you wont find a better place to enjoy horses and the best summer camps. At Rockin N Stables we strive to give you, your family and your guests the best horse back riding experince. All of our horses are laid back and friendly.
4
Underground Atlanta
50 Upper Alabama St SW, Atlanta, GA 30303-3192
Known as “the city beneath the city,” Underground Atlanta has been the cultural heart of Downtown Atlanta since the 1900s. From basement speakeasies to the annual Peach Drop (where an 800-pound peach is dropped from the top of a building to ring in the new year), this arts, entertainment, and retail district has seen it all. Today, Underground Atlanta offers a multifaceted cultural experience featuring a virtual reality gallery, music clubs, and restaurants. travelers can also enjoy outdoor concerts, festivals, artisan markets, and more. This vibrant hub is conveniently connected to the Five Points train station, and just a short stroll from the scenic Broad Street Boardwalk. – Tripadvisor
5
Ponce City Market
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
6
Johnny's Hideaway
3771 Roswell Rd NE, Atlanta, GA 30342-4414
7
River Gallery
400 E 2nd St, Chattanooga, TN 37403-1105
Craft and art collections.
8
Lane Motor Museum
702 Murfreesboro Pike, Nashville, TN 37210-4522
Lane Motor Museum in Nashville features the largest European collection of cars and motorcycles in the United States. Admission for adults aged 18-64 is $15; Admission for Youths aged 6-17 is $3; Admission for seniors 65+ is $10; Children under 5 are always free. There is plenty of FREE parking.
9
Amber Falls Winery Nashville
349 Opry Mills Dr Suite 751A, Nashville, TN 37214-2437
Amber Falls Winery Nashville is proud and excited to be the first and only winery at Opry Mills Mall! We are a satellite store for Amber Falls Winery & Cellars in Hampshire, TN. Our mission is to bring the same exceptional customer service and award-winning wine to Nashville! We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. Something new that we are excited about is selling our delicious WineTeaZers in growlers! Enjoy it anywhere and then bring your growler back for more! So swing by and taste some of our wine, sit and sip on a glass with friends and then take a few bottles home to enjoy!
10
AxeVentures
2416 Music Valley Dr Suite 151, Nashville, TN 37214-1011
At AxeVentures, we do more than just throw axes for fun. Rooted in ancient warfare and trailblazing, we offer a unique opportunity to tap into your primal and wildly adventurous self. Imagine a game of darts, but more extreme and exciting.
11
Bicentennial Capitol Mall State Park
600 James Robertson Pkwy, Nashville, TN 37243-3081
This 19 acre park in the heart of Nashville serves as a monument to the bicentennial celebration of the State of Tennessee. This park offers plenty of opportunities to learn about the long history of Tennessee while having a great experience in a beautiful green space. More information on this park and many more can be found at the TN State Parks website.
12
Tennessee State Museum
1000 Rosa L Parks Blvd, Nashville, TN 37208-2624
The Tennessee State Museum is located at the corner of Rosa L. Parks Blvd. and Jefferson Street at Bicentennial Capitol Mall State Park. It is designed to bring history to life. It includes a “Tennessee Time Tunnel” chronicling the state’s rich history and leading visitors though the Museum’s permanent collection, a hands-on children’s gallery, six rotating galleries, a state-of-the art digital learning center and a two-story Grand Hall. Exhibitions include significant artifacts related to the state’s history, along with displays of art, furniture, textiles, and photographs produced by Tennesseans. The Museum's Civil War holdings of uniforms, battle flags and weapons are among the finest in the nation.There is no admission charge for visitors. Hours are subject to change. Please check our website at tnmuseum.org for the most up to date information on parking, exhibitions and events.
13
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
14
Boystown
Chicago, IL
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
15
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
16
The Riverside Theater
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
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OVERVIEW

Get ready for an epic adventure as we embark on an incredible journey from the Sunshine State of Florida to the bustling city of Milwaukee in Wisconsin. Along the way, we'll traverse a vast tapestry of landscapes, from sun-kissed beaches to rolling hills and vibrant metropolises. Brace yourself for a thrilling expedition filled with unforgettable experiences and memories that will last a lifetime.

Our adventure will lead us through a diverse array of states, each with its unique charm and character. We'll marvel at the towering skyscrapers of bustling cities, meander through quaint towns steeped in history, and soak up the beauty of serene countryside vistas. Imagine the excitement of exploring new places, discovering hidden gems, and immersing ourselves in different cultures.

As we journey northward, the scenery will transform before our eyes. The warmth of the southern sun will gradually give way to the crisp air of the Midwest, and lush greenery will paint the landscape in vibrant hues. With every mile we travel, we'll create memories that will stay with us long after the journey's end. So buckle up and get ready for an unforgettable road trip that will ignite your imagination and leave you with a newfound appreciation for the wonders of our nation.

1
Start:Rogers Farm
Gainesville, Florida·
3.5
(6) review
3831 NW 156th Ave, Gainesville, FL 32609-5028
2
Underbelly
Jacksonville, Florida·
3.5
(9) review
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
113 E Bay St, Jacksonville, FL 32202-3414
3
Rockin N Stables
Tallahassee, Florida·
4.5
(5) review
We offer trail rides, riding lessons, birthday parties and summer camps. If you love horseback riding, you wont find a better place to enjoy horses and the best summer camps. At Rockin N Stables we strive to give you, your family and your guests the best horse back riding experince. All of our horses are laid back and friendly.
5178 Mount Olive Rd, Tallahassee, FL
4
Underground Atlanta
Atlanta, Georgia·
2.0
(976) review
Known as “the city beneath the city,” Underground Atlanta has been the cultural heart of Downtown Atlanta since the 1900s. From basement speakeasies to the annual Peach Drop (where an 800-pound peach is dropped from the top of a building to ring in the new year), this arts, entertainment, and retail district has seen it all. Today, Underground Atlanta offers a multifaceted cultural experience featuring a virtual reality gallery, music clubs, and restaurants. travelers can also enjoy outdoor concerts, festivals, artisan markets, and more. This vibrant hub is conveniently connected to the Five Points train station, and just a short stroll from the scenic Broad Street Boardwalk. – Tripadvisor
50 Upper Alabama St SW, Atlanta, GA 30303-3192
5
Ponce City Market
Atlanta, Georgia·
4.5
(992) review
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
6
Johnny's Hideaway
Atlanta, Georgia·
3.5
(95) review
3771 Roswell Rd NE, Atlanta, GA 30342-4414
7
River Gallery
Chattanooga, Tennessee·
4.5
(98) review
Craft and art collections.
400 E 2nd St, Chattanooga, TN 37403-1105
8
Lane Motor Museum
Nashville, Davidson County, Tennessee·
4.5
(971) review
Lane Motor Museum in Nashville features the largest European collection of cars and motorcycles in the United States. Admission for adults aged 18-64 is $15; Admission for Youths aged 6-17 is $3; Admission for seniors 65+ is $10; Children under 5 are always free. There is plenty of FREE parking.
702 Murfreesboro Pike, Nashville, TN 37210-4522
9
Amber Falls Winery Nashville
Nashville, Davidson County, Tennessee·
4.5
(9) review
Amber Falls Winery Nashville is proud and excited to be the first and only winery at Opry Mills Mall! We are a satellite store for Amber Falls Winery & Cellars in Hampshire, TN. Our mission is to bring the same exceptional customer service and award-winning wine to Nashville! We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. Something new that we are excited about is selling our delicious WineTeaZers in growlers! Enjoy it anywhere and then bring your growler back for more! So swing by and taste some of our wine, sit and sip on a glass with friends and then take a few bottles home to enjoy!
349 Opry Mills Dr Suite 751A, Nashville, TN 37214-2437
10
AxeVentures
Nashville, Davidson County, Tennessee·
5.0
(89) review
At AxeVentures, we do more than just throw axes for fun. Rooted in ancient warfare and trailblazing, we offer a unique opportunity to tap into your primal and wildly adventurous self. Imagine a game of darts, but more extreme and exciting.
2416 Music Valley Dr Suite 151, Nashville, TN 37214-1011
11
Bicentennial Capitol Mall State Park
Nashville, Davidson County, Tennessee·
4.5
(969) review
This 19 acre park in the heart of Nashville serves as a monument to the bicentennial celebration of the State of Tennessee. This park offers plenty of opportunities to learn about the long history of Tennessee while having a great experience in a beautiful green space. More information on this park and many more can be found at the TN State Parks website.
600 James Robertson Pkwy, Nashville, TN 37243-3081
12
Tennessee State Museum
Nashville, Davidson County, Tennessee·
4.5
(997) review
The Tennessee State Museum is located at the corner of Rosa L. Parks Blvd. and Jefferson Street at Bicentennial Capitol Mall State Park. It is designed to bring history to life. It includes a “Tennessee Time Tunnel” chronicling the state’s rich history and leading visitors though the Museum’s permanent collection, a hands-on children’s gallery, six rotating galleries, a state-of-the art digital learning center and a two-story Grand Hall. Exhibitions include significant artifacts related to the state’s history, along with displays of art, furniture, textiles, and photographs produced by Tennesseans. The Museum's Civil War holdings of uniforms, battle flags and weapons are among the finest in the nation.There is no admission charge for visitors. Hours are subject to change. Please check our website at tnmuseum.org for the most up to date information on parking, exhibitions and events.
1000 Rosa L Parks Blvd, Nashville, TN 37208-2624
13
Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
333 Michigan Ave, Chicago, IL 60601-3901
14
Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
Chicago, IL
15
Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
1060 W. Addison St., Chicago, IL 60613-4566
16
The Riverside Theater
Milwaukee, Wisconsin·
4.0
(95) review
116 W Wisconsin Ave, Milwaukee, WI 53203-2503

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FAQ
Frequently Asked Questions
What's the driving distance between Jacksonville and Milwaukee?
The distance is 1,146 miles
What's the travel time between Jacksonville and Milwaukee?
The driving time can vary depending on traffic conditions, but it is typically 21h 32m mins in normal traffic
What are some of the best cities to visit between Jacksonville and Milwaukee?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Milwaukee?
There are plenty! Here are some stops you shouldn’t miss on your way to Milwaukee
What’s the weather like in Milwaukee?
The weather in Milwaukee is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Milwaukee in January
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Interested in a detailed plan for your time in Milwaukee?
Plan your dream Milwaukee trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Milwaukee
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Where else can I travel to if I'm starting my trip in Jacksonville?
We have a lot of great trip options for Jacksonville! See the links below for all the itineraries we created for you
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