Top Milwaukee Private and Luxury

The Milwaukee Downtown ride takes you on a on an exhilarating helicopter journey down the Milwaukee Bay where you can witness Downtown Milwaukee like never before! This ride offers a truly unique perspective, soaring directly over the heart of the city. You’ll be treated to sweeping views of the Milwaukee River, the iconic Hoan Bridge, and the majestic Milwaukee Art Museum. But that’s not all – this ride encompasses the entire cityscape, ensuring you don’t miss a single landmark.

Milwaukee is known for its beer, brats, baseball, and lakefront scenery, but it offers much more than most travelers realize. Learn about the city through the eyes of a resident guide on this Milwaukee sightseeing tour, see famous attractions, trendy neighborhoods, an art-filled alley, and so much more—including a bronze statue of the Fonz of “Happy Days” fame.

As seen on BBC, NBC, and featured on Netflix’s Dark Tourist, this is one of the most talked-about true crime tours in the world. The Cream City Cannibal Tour explores one of Milwaukee’s most infamous criminal cases—walking through the exact neighborhood where multiple events connected to a notorious serial killer took place. This is not a casual history tour. Through guided storytelling, guests are led through the psychological, cultural, and real-world impact of the case, offering insight into how it unfolded and why it continues to be studied today. The tour has even been referenced in academic settings, including university psychology and criminal justice programs. Expect a deeper, more intense experience—focused on understanding, not sensationalizing. Outdoor tour. Rain or shine. Not recommended for those sensitive to true crime content.

Unveil the dark history of Brew City with this ghost tour of the city’s most haunted locations. Meet your guide for a ghoul-fueled stroll through the heart of Milwaukee to take in spirit-infested historic hotels, theaters, and even skyscrapers. Be entertained by bone-chilling ghost stories and tales of paranormal activity as you delve into Milwaukee’s ghoulish past.

The Midwestern city of Milwaukee is known for its beer and cheese and this walking food tour gives you a taste of the best. Join a small group and enjoy a walk through "Brew City" to sample a number of beers and regional snacks. Learn about the 19th-century Germanic population that immigrated to the area and its influence on today's local cuisine.

One of the most haunted bars in the nation, Shaker’s Cigar Bar—a Milwaukee institution formerly owned by the infamous Al Capone—has a history as wild as its ghostly encounters. On this small-group tour, explore behind the scenes, hearing stories about its Prohibition-era connections, the bar's cemetery and brothel past, and accounts of lingering spirits. Part history tour, part paranormal experience, this tour is not for the faint of heart.

Milwaukee is a city shaped by its waterways, its waves of immigrants, and its bold spirit-famous for its German heritage, its brewing traditions, and its knack for reinvention over nearly two centuries. Our journey today starts at Wisconsin Historical Marker three three three, which marks the heart of old Kilbourntown, walk through stories of rivalry, resilience, and remarkable change, all the way to the bustling Milwaukee Public Market in the Historic Third Ward. Go at your own pace. The tour never expires. This is a hand free experience, press play and put your phone in your pocket. The tour is location aware, and plays as you walk. It never expires.

Milwaukee is called many names; Brew City, City of Festivals, and Cream City, but it is most recognized as the place for great beer and cheese in the Upper Midwest. The large 19th century Germanic population continue to influence our local food products and dishes while some of the best restaurants from the historic Third Ward to East Town Downtown. When booking our winter exclusive Skywalk Food Tour you'll get to experience and enjoy all the best we have to offer from a warm second-story perspective. You'll get to experience and enjoy all the best we have when you book our Secret Food Tour: Milwaukee. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Kick off your morning with a guided e-bike tour around Milwaukee. Covering about 15 miles, you’ll ride through historic neighborhoods and scenic parks, with stops including the North Point Lighthouse and Villa Terrace Museum and Gardens. Capped at eight for a personalized experience, this tour is a fun, active way to pack in plenty of sightseeing. Hear facts and insights from your guide along the way.

Half the history talk calories of the Old Milwaukee Tour but with all the full bodied flavor! Ride 15 miles on a pedal assist e-bike through the best of Milwaukee. Enjoy a frozen custard at the beach, a local speciality. See incredible variety! Ride through historic working class neighborhoods and past ornate mansions that were built when Milwaukee was the machine shop of the world. Admire hidden alley street art. Gaze up at massive frescos inside our finest cathedral. Cruise along lakeshore parks and past downtown architectural gems. Wrap it all up with a visit to a beer garden, a city tradition since 1848, and you'll have a real taste of Milwaukee.

Find out about Milwaukee’s dark history and most haunted places with this ghost-themed tour. Opting for a private tour means you’ll hear your guide clearly and can ask all the questions you want along the way. Find out about the city’s devastating fires in 1892 and the ghosts that are still believed to haunt the city. Learn about apparitions in a pub’s basement and bathroom mirrors, and visit the city’s most haunted location.

Guests will learn about Milwaukee’s thriving brewpub scene and visit four separate breweries, tasting up to 16 different beers on this guided brewery tour with a snack. Visit some of Milwaukee's most popular brewpubs, including Lakefront Brewing, Broken Bat Brewing Co, Ope!, Gathering Place, and Wizard Works, to name a few. Round trip transportation by bus in downtown Milwaukee is included. Please try to book your tour at least 72 hours in advance of the tour to confirm availability. Tours book up quickly, and tours booked inside this window may not have room.

Our guided City Skyline Kayak Tours are 1.5–2 hours long and follow the Milwaukee River up towards downtown Milwaukee. We do not make any stops along the way for this tour, but we do provide details about Milwaukee's history and attractions along the river. Our knowledgeable guides will provide you with any kayaking instruction you may need and ensure you feel safe and comfortable on this beginner-level tour.

The Historic Third Ward was the first stop for many of Milwaukee's European immigrants, particularly the Irish and later the Italians. Close to cheap housing and available jobs, these new arrivals created close-knit communities. Like most major industrial cities, the Third Ward had a significant and destructive fire in 1892, which reshaped the landscape to much of what you see today. In the 1970s, this area experienced a resurgence that transformed factories and warehouses into condos and mixed adaptive reuse. On this tour, learn about the neighborhood landscape as well as the Irish and Italian immigrants as well as the impact of the LGBTQ+ community and other residents. Stops include the Milwaukee Public Market (2005), Milwaukee Institute of Art and Design (MIAD) (1974), and Commission Row (1894). This walking tour is 1 mile in length. Travelers are recommended to bring (weather permitting): good walking shoes, water, sunscreen, and/or umbrella.

Step back into Milwaukee’s Prohibition era and uncover a world of speakeasies, madams, gangsters, corruption, and scandal. The Whorin’ 20s Walking Tour explores the city’s notorious vice district during the Roaring Twenties, when bootleggers, brothel owners, politicians, and organized crime figures helped shape Milwaukee’s nightlife and underground economy. Led by expert storytellers, this entertaining and historically grounded walking tour reveals the hidden stories behind the city’s most colorful characters and forgotten locations. Along the way, guests will discover how Prohibition transformed Milwaukee and why the era continues to captivate visitors nearly a century later. Perfect for history enthusiasts, groups, couples, bachelorette parties, and anyone looking for a different side of Milwaukee beyond breweries and ballgames. Bride goes free with qualifying bachelorette party reservations.

If you've already seen most of the sights of Milwaukee, get a different perspective on the city with this haunted history walking tour of Lake Geneva. As you stroll in a small group, your guide will fill you in on all the colorful history and characters, from haunted mansions and vengeful spirits to lake monsters and more.

Explore Sheboygan’s highlights in a fun way, on a Segway, on this small-group excursion. Cruise along the Sheboygan River and Lake Michigan shoreline to see the lighthouse, shipwreck sites, schooner remains, and the John Michael Kohler Arts Center. If you’d like, you can upgrade to a private tour for a more personalized experience.

Set on a bluff, overlooking the northern point of Milwaukee’s harbor, this neighborhood boasts an incredible collection of mansions from the early twentieth century. The tree-lined blocks feature a variety of styles including German Renaissance Revival, English Tudor Revival, Mediterranean Revival and others popular from 1890-1940. The houses were designed by some of the most notable Milwaukee architects including Eschweiler, Clas, Niedecken and even Wisconsin’s own Frank Lloyd Wright. Beyond the architectural details, the neighborhood’s past residents include many prominent Milwaukeeans who made money in wheat, railroads, straw hats, fur coats, ice cream and more. The tour also includes non-residential neighborhood landmarks like a historic hospital complex, water tower and lighthouse, as well as a Frederick Law Olmsted designed park. This walking tour is 1.4 miles in length. We recommend bringing (weather permitting): good walking shoes, water, sunscreen, and/or umbrella.

Like many communities in the industrial Midwest, Milwaukee’s ecological legacy has a significant period of pollution. Thankfully, in the late 1980s & early 1990s, driven by Mayor John Norquist and others, Milwaukee dedicated resources to water clean up and the reinvigoration of the buildings along the Milwaukee River. This reinvestment included the creation of a public-private partnership known as the Riverwalk (1993). Today, the Riverwalk extends 3.1 miles along both sides of the Milwaukee River, from the site of the former North Avenue Dam, through Downtown and the Historic Third Ward to Lake Michigan. The tour will explore the industries and early city growth that impacted the river so greatly and also a number of the historic buildings along the way. You’ll also learn about some of the temporary and permanent public art on display. This walking tour is 1.2 miles in length. We recommend that travelers bring: good walking shoes, water, sunscreen, and/or umbrella.

Downtown Milwaukee's growth began around the intersection of N. Water St. and E. Wisconsin Ave. but expanded quickly as the small settlement became a large city. If you are looking for an introduction to Milwaukee's history, this is the best place to start. The tour will explore this commercial district from the earliest beginnings at the river's edge all the way to the modern office buildings along Lake Michigan's shore. Stops on the tour include a variety of architectural styles including Alexander Eschweiler's Art Deco Gas Light Building (1930), the Richardsonian Romanesque style Federal Building (1892), and Northwestern Mutual's Neoclassical Headquarters (1914). This walking tour is 1 mile in length. We recommend that travelers bring (weather permitting): good walking shoes, water, sunscreen, and/or umbrella.

Get to know one of Milwaukee‘s most haunted neighborhoods, Westown, and discover why Marquette University is considered one of the nation‘s most haunted schools. On this self-guided walking tour, you‘ll visit eleven haunted locations and hear some of Milwaukee‘s most spook-tacular tales! Starting in front of the Milwaukee Public Museum, you‘ll stroll around Marquette Campus and along Wisconsin Ave to Straz Tower, where our tour ends. Along the way, you‘ll meet some of Milwaukee‘s most famous ghosts, including a professor who continues to report to work, and a home-proud beer baron. You‘ll also see the site of one of the city‘s most notorious murders. Lace up your shoes and join me in discovering the haunted side of this historic neighborhood. This family-friendly hour-long walk does contain content that may be disturbing, including details of murders, mentions of suicide and accidental deaths. Please use caution when selecting this tour for very young or sensitive audiences.

Explore Milwaukee’s criminal underworld on the Mobsters and Mafia Tour, a guided walking experience that uncovers the rise and fall of the Milwaukee Mob and the powerful Balistrieri crime family. Visit historic locations while discovering how organized crime, political influence, and underground enterprises shaped the city throughout the 20th century. Hear captivating stories of power, loyalty, corruption, and betrayal as your guide reveals the real people and events behind one of Milwaukee’s most fascinating chapters. While the tour touches on the city’s Prohibition-era roots, its primary focus is the Milwaukee Mob and the figures who dominated the city’s underworld from the 1960s through the 1980s. Perfect for history enthusiasts, true crime fans, and curious travelers seeking a side of Milwaukee few visitors ever discover.

This private walking tour reveals the cultural heritage of Milwaukee. Explore historic streets shaped by American industry and artistic growth. Discover a city whose legacy reflects transformation and modern identity. Begin near the statue of General Douglas MacArthur. Learn how leadership and history shaped this urban landscape. Walk through vibrant districts filled with architectural character. What stories define Milwaukee’s cultural evolution? The Milwaukee County War Memorial Center presents a powerful historical tribute. Nearby, the Milwaukee Art Museum showcases a refined artistic heritage. Its striking design reflects contemporary architectural vision. The journey continues to Lakeshore State Park. This waterfront setting offers calm views and fresh perspectives. Capture memorable moments while exploring one of the city’s scenic spaces. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience