Welcome to the ultimate Wisconsin self-drive adventure.
This curated road trip loops through the very best of the Badger State, starting and ending in the vibrant lakeside city of Milwaukee. Your journey blends urban sophistication with breathtaking natural wonders, tracing a scenic path across diverse landscapes. You will experience everything from rolling farmland and dramatic river valleys to pristine shorelines and historic maritime villages. It is a drive designed for those who love discovery, freedom, and the open road.
Leaving Milwaukee, your route heads west into the cultural heart of the state. You will explore Madison, Wisconsin's dynamic capital city nestled between two stunning lakes, before diving into the architectural wonders of Spring Green. From there, the journey meets the mighty Mississippi River in La Crosse. You will then cruise north along the iconic Wisconsin Great River Road, a designated National Scenic Byway offering unparalleled cliffside views, historic towns, and sweeping river vistas that capture the timeless spirit of the American Midwest.
The final leg of your expedition ventures into Wisconsin’s legendary northern and eastern waterscapes. You will discover Bayfield, the peaceful gateway to the Apostle Islands National Lakeshore on Lake Superior, before heading south toward the historic football haven of Green Bay. Finally, you will unwind in Door County, often called the Cape Cod of the Midwest, where orchard-lined roads and lakeside lighthouses guide you back down the Lake Michigan coast to Milwaukee.
This road trip promises an unforgettable mix of local flavor, rich history, and majestic scenery.
Tour starts and ends in Milwaukee, WI
2 nights - Milwaukee, 1 night - Madison, 1 night - Spring Green, 1 night - La Crosse, 1 night - Prescot,
2 nights - Bayfield, 2 nights - Green Bay, 2 nights - Door County, 1 night Milwaukee.
Days 1 & 2 - Milwaukee, WI.
Start your Wisconsin adventure with two amazing days in Milwaukee, recently recognized on National Geographic’s “Best of the World” list. Start by visiting the Harley-Davidson Museum, one of Milwaukee’s standout attractions dedicated to the history, engineering, and culture of the iconic American motorcycle manufacturer. You’ll see hundreds of original motorcycles including the very first Harley-Davidson, celebrity bikes, interactive displays and photo opportunities that allow visitors to sit on the current year collection of motorcycles. The museum campus also includes the MOTOR Bar & Restaurant and scenic riverfront green space along the Menomonee River.
Slow your pace with a stroll along the 3.7-mile Milwaukee Riverwalk, one of the best ways to experience Milwaukee and its historic neighbourhoods. This pedestrian-friendly path offers seamless access to waterside dining, public art, and lively brewpubs.
The Milwaukee Public Market is an iconic, award-winning indoor food hall and artisanal marketplace located in the heart of the Historic Third Ward neighbourhood. Repeatedly voted the #1 Best Public Market in the Country, this vibrant community hub features 18 locally owned independent vendors offering diverse global cuisines, fresh regional specialties, and artisan retail items.
The Milwaukee Art Museum is a breath-taking, lakefront white post-modern masterpiece designed by Santiago Calatrava. In addition to the art collection, the museum features the iconic Burke Brise Soleil, a 90-ton moveable sunscreen with a 217-foot wingspan that resembles giant wings. The wings open with the museum at 10:00 AM, flap at noon, and fold closed at night.
2 Nights: Milwaukee
Hotel: Kimpton Journeyman Hotel, Room Only
Day 3 – Milwaukee, WI – Madison, WI. (80 miles)
Check out of your hotel and head west along I-94 to Madison to visit the Wisconsin State Capitol Building, one of the most impressive buildings in Madison. The building was designed in a grand neoclassical style and is especially striking as its white granite dome is one of the largest domes in the world making it the tallest of any state capitol buildings in the United States.
Stroll down State Street, a famous car-free pedestrian street that spans eight blocks that directly connects the Wisconsin State Capitol with the University of Wisconsin–Madison campus.
State Street ends at The Memorial Union Terrace, Madison’s premier lakeside gathering space located on the University of Wisconsin-Madison campus. Famous for its iconic sunburst chairs, outdoor dining, seasonal concerts, breath-taking sunsets over Lake Mendota, and vibrant community atmosphere.
1 Night: Madison
Hotel: The Edgewater Hotel, Room Only
Day 4 – Madison, WI – Spring Green, WI. (45 miles)
A short drive from Madison to Spring Green brings you to Taliesin, the home of America’s most-famous architect Frank Lloyd Wright. The historic 800-acre estate, home, studio, and school served as his primary residence and a lifelong "living laboratory" for his philosophy of organic architecture. The estate’s many buildings and the surrounding grounds showcase how Wright designed structures to blend into the natural Wisconsin terrain. The estate was designated a National Historic Landmark in 1976 and inscribed as a UNESCO World Heritage Site in 2019.
Consider having lunch at the estate’s Riverview Terrace Café, situated inside the Frank Lloyd Wright Visitor Center, featuring dramatic panoramic views overlooking the Wisconsin River.
1 Night: Spring Green
Hotel: The Spring Valley Inn, Room Only
Day 5 – Spring Green, WI – La Crosse, WI. (90 miles)
The drive from Spring Green to La Crosse routes you through the Driftless Area of Wisconsin, a unique, unglaciated region in the southwestern part of the state famous for its rugged topography, towering bluffs, and deeply carved river valleys. As you approach La Crosse, you’ll notice the landscape change as you descend from towering bluffs and enter the Mississippi River valley.
Before heading into town, visit Grandad Bluff County Park for panoramic views over the entire Mississippi River valley. On a clear day you can see across three states: Wisconsin, Minnesota, and Iowa.
Enjoy a sunset cruise on The La Crosse Queen, a paddlewheel riverboat that offers scenic, narrated tours along the Upper Mississippi River. The La Crosse Queen stands out as one of the few vessels in the United States that is still strictly propelled by its sternwheels.
1 Night: La Crosse
Hotel: The Charmant Hotel, Room Only
Day 6 – Drive The Wisconsin Great River Road. (115 miles)
Depart early and head north on Highway 35, the Wisconsin Great River Road. The route is designated an All-American Road and a National Scenic Byway which has been repeatedly voted America's #1 scenic drive, showcasing dramatic bluffs, historic river towns, and an ever-growing wine trail, all with stunning views of the Mississippi River.
A notable stop along the route includes Pepin, home to Laura Ingalls Wilder, author of the Little House on the Prairie book series highlighting the author’s 19th-century childhood on the American frontier. Travel several miles north to Stockholm for a slice of pie at the Stockholm Pie and General Store, recognized as a top pie shop in America by the USA Today Readers' Choice awards.
Follow Highway 35 north to Prescott where your route diverges from the Mississippi River and continue north along the blue waters of the St. Croix River. Enjoy an afternoon excursion on the Wisconsin Great Northern Railroad, a premier historic excursion train located in Trego, Wisconsin. The train operates scenic, dining, and overnight train rides along a 26-mile slow-paced sightseeing trips through forests, lakes and rural Wisconsin countryside.
1 Night: Prescott
Hotel: The Port of Prescott - Boutique Hotel, Room Only
Day 7 & 8 – Prescott, WI – Bayfield, WI. (210 miles)
Continue north to Hayward, home to the Fred Scheer’s Lumberjack Show, a premier seasonal lumberjack show held in the historic Lumberjack Bowl. This family-friendly show features world-class timber athletes competing in 10 different events, including log rolling, axe throwing, speed climbing, and power sawing, all mixed with comedy and Northwoods history.
Check into your Bayfield hotel for 2 nights to enjoy the stunning shoreline of “greatest of the Great Lakes” - Lake Superior. Wander through downtown Bayfield’s small streets where you can enjoy cafés, shops, galleries and a charming waterfront and marina area.
The Apostle Islands Cruises is the official National Park Service concessioner offering sightseeing tours, lighthouse excursions, and island shuttles to the Apostle Islands National Lakeshore, Wisconsin’s only National Park property. Or take the Madeline Island Ferry to Madeline Island to explore quiet laid-back island beaches, forest roads, and open lake scenery that feels more relaxed than the mainland.
2 Nights: Bayfield
Hotel: The Seagull Bay - A Lakeside Motel, Room Only
Days 9 & 10 – Bayfield, WI – Green Bay, WI. (280 miles)
Depart early for a Northwoods journey to Wisconsin’s other Great Lake – Lake Michigan.
Visit Copper Falls State Park, one of Wisconsin’s most ruggedly beautiful parks famous for deep volcanic gorges and roaring cascading waterfalls.
Stop for lunch in the iconic Northwoods community of Eagle River, celebrated as both the "Snowmobile Capital of the World" and home to the world's largest chain of freshwater lakes. Continue south to the Menominee Logging Camp Museum in Keshena. Owned and operated by the Menominee Indian Tribe of Wisconsin, this historical site highlights the state’s early logging industry and the tribe's legendary sustainable forestry traditions.
Plan for a late afternoon arrival in Green Bay, home of the famous NFL team the Green Bay Packers – and the only NFL team that is publicly owned as a community-backed non-profit corporation. The Lambeau Field Stadium Tours offer fans an insider look at the historic home of the team, with routes walking through the Lambeau Field Atrium, premium seating areas, and the iconic player tunnel. The Green Bay Packers Hall of Fame chronicles over a century of franchise history across nine permanent galleries, featuring interactive displays, legendary game artifacts, and the team's championship trophies which helps explain why the Packers are such a unique community-owned and loved football team.
Take a scenic break from the sports theme, with a stroll along the Fox River Trail, great for walking, cycling or relaxing by the water. Explore the Bay Beach Wildlife Sanctuary, where you will be able to see local wildlife and walk through wetlands and wooded trails. The nearby Bay Beach Amusement Park is a historic, city-owned amusement park known for its retro charm and incredible affordability. The park's famous wooden roller coaster, the Zippin’ Pippin, is an exact replica built from the blueprints of Elvis Presley’s favourite coaster from Memphis, Tennessee.
2 Nights: Green Bay
Hotel: Lodge Kohler, Room Only
Day 11 & 12 – Green Bay, WI – Door County, WI. (50 miles)
Travel from the city of Green Bay along the scenic shoreline of Green Bay to the quieter coastal landscape of Door County, which is often called the "Cape Cod of the Midwest”.
The scenic peninsula, with over 300 miles of spectacular Lake Michigan shoreline, is a beloved destination featuring 11 historic lighthouses, 5 pristine state parks, and dozens of charming coastal communities and small harbour towns.
Once you’ve checked in at your accommodation, visit Peninsula State Park – a large costal park with forest trails, rocky shoreline views, and Eagle Tower, a famous 60-foot-tall wooden observation landmark perched atop Eagle Bluff. The 850-foot-long Canopy Walk is an ADA-accessible wooden ramp that gently winds through the forest treetops up to the observation deck offering panoramic views of Green Bay, surrounding islands and the historic village of Ephraim.
Make dinner reservations to experience a classic Door County fish boil. This historic, performance-driven culinary tradition includes fresh Lake Michigan whitefish, red potatoes, and onions - all cooked outdoors in a large kettle over an open wood fire. Finish your flaky fish dinner with a slice of authentic, tart Door County cherry pie for dessert.
Spend the evening enjoying Door County’s legendary live theatre scene, blending professional theatrical companies with Broadway-quality performances in an outdoor setting under a canopy of cedar trees or catch an indoor show at one of the peninsula’s unforgettable venues.
Nature lovers won’t want to miss a night-time trip to Newport State Park, highly celebrated for holding an International Dark Sky Park designation, making it one of the premier locations in the country for stargazing, viewing the Milky Way, and catching the northern lights.
2 Nights: Door County
Hotel: Glidden Lodge Beach Resort - Sturgeon Bay, Room Only
Day 13 & 14 -Door County, WI – Milwaukee, WI. (150 miles)
Depart Door County for your drive south along the Lake Michigan shoreline with several optional stops on your way back to Milwaukee.
Consider a short stop in Manitowoc to visit the Wisconsin Maritime Museum, the largest maritime museum on the Great Lakes, offering an immersive look into Wisconsin's rich shipping, shipbuilding, and shipwreck history. The museum is also home to SS Cobia – a perfectly preserved WW2 submarine.
Schedule a lunch stop or some final Lake Michigan beach-time at Kohler-Andrae State Park located in the coastal city of Sheboygan – nicknamed “The Malibu of the Midwest”.
Return to Milwaukee for your last night of the tour.
1 Night: Milwaukee
Hotel: Kimpton Journeyman Hotel, Room Only
TOUR COST
All 'from' prices quoted below are per adult person, per package in £ GBP
The exact cost of the tour will depend on the date of travel and the availability at the time you book.
Your holiday includes:
Return flights to Milwaukee
13 Nights accommodation as above including all taxes
Breakfast as stated above
Car hire including all taxes, fees, unlimited mileage and breakdown cover.
October - March = From £1,899 per person based on 2 adults sharing
June - September = From £2,399 per person based on 2 adults sharing
Pre, post or extra nights
Pre, post & extra nights within the itinerary are available to be added to this tour, please let us know at time of booking if you would like to extend your stay anywhere and we will be happy to quote the extra nights.
