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12-Day Roadtrip from Milwaukee to Charleston Itinerary

Last updated: 2024 Jun 28

Exploring Milwaukee's Iconic Sites

Morning

Start your day with a visit to Milwaukee Art Museum. This architectural marvel houses over 25,000 works of art and offers stunning views of Lake Michigan. After soaking in the art and architecture, head to Colectivo Coffee for a refreshing coffee break.

Afternoon

In the afternoon, join the Milwaukee: Local Food Tour. This tour will take you through some of Milwaukee's best eateries in the Historic Third Ward. You'll get to sample local delicacies and learn about the city's culinary history. Post-tour, stroll around the Historic Third Ward to explore its boutiques and galleries.

Evening

End your day with a visit to Lakefront Brewery. Take their entertaining brewery tour and enjoy some of their finest brews. For dinner, head over to Sanford Restaurant, known for its exquisite fine dining experience.

Bedtime

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Milwaukee Art Museum
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Milwaukee: Local Food Tour
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Historic Charm and Scenic Views

Morning

Begin your second day with a visit to North Point Lighthouse. This historic lighthouse offers panoramic views of Lake Michigan and the surrounding area. Afterward, grab breakfast at Blue's Egg, famous for its creative breakfast dishes.

Afternoon

Spend your afternoon exploring Lake Park, designed by Frederick Law Olmsted. Enjoy a leisurely walk through its beautiful landscapes. Then head over to Café Hollander for lunch on their lovely patio.

Evening

In the evening, join the intriguing Milwaukee: Macabre Milwaukee Walking Tour. Discover Milwaukee's darker history as you walk through its haunted sites. For dinner, dine at Bacchus - A Bartolotta Restaurant, offering an elegant dining experience with stunning views.

Bedtime

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North Point Lighthouse
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Lake Park
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Culture and Entertainment in Milwaukee

Morning

Kick off your third day with a visit to Chudnow Museum of Yesteryear, where you'll step back in time and explore exhibits showcasing life in early 20th-century America. Enjoy breakfast at Honeypie Cafe, known for its hearty morning meals.

Afternoon

In the afternoon, embark on an exciting adventure with the Milwaukee: Private City Scavenger Hunt. This interactive tour will have you solving clues and discovering hidden gems around the city. Afterward, relax at Anodyne Coffee Roasting Co. with a cup of their freshly roasted coffee.

Evening

Conclude your day by visiting the iconic Pabst Theater for an evening show or concert. For dinner before or after the show, try out Ristorante Bartolotta dal 1993, offering authentic Italian cuisine in a cozy setting.

Bedtime

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Chudnow Museum of Yesteryear
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Milwaukee: Private City Scavenger Hunt
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Milwaukee's Hidden Gems

Morning

Start your day with a visit to Marquette University. Explore the beautiful campus and its historic buildings. Afterward, enjoy a delicious breakfast at Café Benelux, known for its Belgian-inspired dishes and rooftop patio.

Afternoon

In the afternoon, head to Bounce Milwaukee for some fun and excitement. This indoor entertainment center offers activities like laser tag, rock climbing, and arcade games. For lunch, stop by Comet Cafe, famous for its comfort food and vegan options.

Evening

End your day with the Milwaukee: Around the Ward in 90 Minutes tour. This guided tour will take you through the Historic Third Ward, showcasing its history and architecture. For dinner, dine at Hinterland Brewery, offering a variety of craft beers and delicious dishes.

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Marquette University
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From Milwaukee to Chicago

Morning

Begin your journey to Charleston with a stop in Chicago. Start your morning with a visit to Millennium Park to see the iconic Cloud Gate sculpture (The Bean). Enjoy breakfast at The Bongo Room, known for its creative brunch dishes.

Afternoon

Milwaukee: Milwaukee Bucks Basketball Game Ticket (if available) or explore Chicago's Magnificent Mile for shopping and sightseeing. Have lunch at Girl & The Goat, one of Chicago's top-rated restaurants.

Evening

Milwaukee: Magic A Private Christmas Lights Tour (if available) or take an evening architecture river cruise to see Chicago's stunning skyline illuminated at night. For dinner, try out Alinea, one of the best fine dining experiences in the city.

Bedtime

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Milwaukee: Milwaukee Bucks Basketball Game Ticket
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Milwaukee: Magic A Private Christmas Lights Tour
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Exploring Indianapolis

Morning

Milwaukee Brewers Baseball Game at American Family Field (if available) or start your day with a visit to the Indianapolis Motor Speedway Museum. Enjoy breakfast at Bluebeard, known for its farm-to-table cuisine.

Afternoon

Milwaukee Scavenger Hunt Adventure (if available) or explore White River State Park, home to several attractions including the Indianapolis Zoo and Indiana State Museum. Have lunch at St. Elmo Steak House, famous for its shrimp cocktail.

Evening

Milwaukee: Private City Scavenger Hunt (if available) or end your day with a visit to Mass Ave Arts District for some shopping and dining. For dinner, try out The Eagle Mass Ave, known for its fried chicken and Southern comfort food.

Bedtime

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Milwaukee Brewers Baseball Game at American Family Field
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Milwaukee Scavenger Hunt Adventure
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Discovering Louisville's Charm

Morning

Start your day with a visit to the Louisville Slugger Museum & Factory. Here, you can learn about the history of baseball bats and even see how they are made. Afterward, enjoy breakfast at Wild Eggs, known for its creative and hearty breakfast dishes.

Afternoon

In the afternoon, take a stroll through the historic Old Louisville neighborhood, famous for its Victorian architecture. Stop by Hillbilly Tea for a refreshing tea break and some light snacks.

Evening

End your day with a visit to the Muhammad Ali Center, dedicated to the life and legacy of the boxing legend. For dinner, head over to 610 Magnolia, offering a fine dining experience with a focus on seasonal ingredients.

Bedtime

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Exploring Nashville's Music Scene

Morning

Charleston: Historic City Tour & Magnolia Plantation Combo (if available) or start your day with a visit to the Country Music Hall of Fame and Museum. Enjoy breakfast at Pancake Pantry, famous for its delicious pancakes.

Afternoon

Charleston: Folly Island Guided Dolphin Boat Tour in Folly Beach (if available) or explore Broadway Street, known for its vibrant music scene and honky-tonk bars. Have lunch at Hattie B's Hot Chicken, known for its spicy fried chicken.

Evening

Charleston: Downtown Evening Haunted History Carriage Tour (if available) or end your day with a visit to The Grand Ole Opry for an unforgettable live music experience. For dinner, try out The Catbird Seat, offering an innovative tasting menu.

Bedtime

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Charleston: Historic City Tour & Magnolia Plantation Combo
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Charleston: Folly Island Guided Dolphin Boat Tour in Folly Beach
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Charming Chattanooga Adventures

Morning

Charleston: Historic City Highlights Guided Bus Tour (if available) or start your day with a visit to Lookout Mountain to see Rock City Gardens and Ruby Falls. Enjoy breakfast at Bluegrass Grill, known for its hearty morning meals.

Afternoon

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch (if available) or explore the Tennessee Aquarium, one of the largest freshwater aquariums in the world. Have lunch at The Terminal Brewhouse, offering great food and craft beers.

Evening

Charleston: Luxury Harbor Dinner Cruise (if available) or end your day with a scenic riverboat cruise on the Tennessee River. For dinner, try out Stir, known for its oysters and craft cocktails.

Bedtime

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Charleston: Historic City Highlights Guided Bus Tour
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Charleston: Schooner Sailing Harbor Tour & Dolphin Watch
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Discovering Atlanta's Rich History

Morning

Start your day with a visit to the Martin Luther King Jr. National Historical Park. Explore the birthplace and church of the civil rights leader and learn about his legacy. Enjoy breakfast at Highland Bakery, known for its delicious pastries and breakfast dishes.

Afternoon

In the afternoon, head to the Georgia Aquarium, one of the largest aquariums in the world. Marvel at the diverse marine life and enjoy interactive exhibits. For lunch, stop by The Varsity, an iconic Atlanta eatery famous for its hot dogs and burgers.

Evening

End your day with a visit to the Atlanta Botanical Garden, where you can stroll through beautiful themed gardens and enjoy seasonal events. For dinner, dine at Bacchanalia, offering a farm-to-table fine dining experience.

Bedtime

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Exploring Savannah's Southern Charm

Morning

Begin your day with a visit to Forsyth Park, a 30-acre park known for its picturesque fountain and walking paths. Enjoy breakfast at Clary's Cafe, a local favorite known for its hearty Southern breakfasts.

Afternoon

In the afternoon, take a guided tour of Savannah's historic district with Charleston: Historic City Tour & Magnolia Plantation Combo. Learn about the city's rich history and see its well-preserved architecture. For lunch, stop by The Collins Quarter, offering Australian-inspired cuisine in a charming setting.

Evening

End your day with a ghost tour through Savannah's haunted sites with Charleston: Downtown Evening Haunted History Carriage Tour. Discover spooky tales and eerie locations as you explore one of America's most haunted cities. For dinner, try out The Grey, located in a restored Greyhound bus terminal offering innovative Southern cuisine.

Bedtime

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Charleston: Historic City Tour & Magnolia Plantation Combo
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Charleston: Downtown Evening Haunted History Carriage Tour
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Charleston's Historic Treasures

Morning

Start your final day with a visit to Fort Sumter National Monument, where you can learn about the start of the Civil War. Enjoy breakfast at Callie's Hot Little Biscuit, known for its delicious biscuits.

Afternoon

In the afternoon, take part in Charleston: Historic City Tour & Magnolia Plantation Combo to explore Charleston's historic sites and beautiful plantation gardens. Have lunch at Husk Restaurant, offering modern Southern cuisine in a historic setting.

Evening

End your trip with an evening harbor cruise on Charleston Harbor with Charleston: Luxury Harbor Dinner Cruise. Enjoy stunning views of the city skyline as you dine on delicious cuisine. For dinner before or after your cruise, try out FIG, known for its farm-to-table dishes.

Bedtime

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