Top Milwaukee Private and Luxury

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.

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.

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.

Swap the big bus tours for a crowd-free experience. Traveling in an open-air, five-seater electric vehicle, you'll thoroughly explore the historic city of Milwaukee, from popular tourist destinations to some hidden gems that most visitors miss. As you travel, your guide will fill you in on Milwaukee's rich and exciting history. This tour has different lengths to suit your schedule.

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.

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.

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.

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.

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.

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.

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.

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.

Explore the culinary delights of Downtown Kenosha on a 3-hour walking food tour. Sample iconic street tacos and the renowned pizza that Kenosha is famous for. Enjoy a unique discussion about Chicagoland's popcorn connection, followed by a refreshing stop at a local brewery. Throughout the journey, delve into the rich food history of Kenosha and the impact of immigration on its vibrant culinary scene. - 3-hour walking tour with 5 delicious food stops - Taste street tacos and Kenosha's famous pizza - Learn about Kenosha's food history and immigration influences - During the tour we will walk by murals and various historic architecture - End the evening with ice cream

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.

Ever wondered what secrets lie beneath the shifting sands of Lake Michigan? Now is your chance to find out. Join us at Simmons Island Beach for an immersive, hands-on metal detecting tour that blends local history with the thrill of the hunt. Whether you’re a curious local or a visiting treasure seeker, this experience offers a unique way to connect with Kenosha’s storied waterfront.

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.

Our tour blends art, street art, architecture and history to provide an informative yet interesting tour. You will be provided excellent views of Lake Michigan and various photography spots for those who love to take pictures. Our goal is to keep prices low while still offering a quality product that is fun for the entire family. The comfort and ease of having everything organized for you takes away the stress when going on holiday. Plus, the extra support and experience of a guide and the chance to travel with and meet like-minded people makes this tour much more attractive. Kenosha is an exciting and vibrant community on the shores of Lake Michigan in Southeastern, Wisconsin. Come enjoy the history and art that make up the Downtown and Harbor Park communities.

Milwaukee, once known as the German Athens, is the most German among major US cities. Walking down Old World Third Street today you are not likely to see many German shops advertising “English Spoken Here” as a special or unique service, but as early as 1848 it would not have been uncommon. Germans represented 1/3 of the entire population in Milwaukee and this section of the city was integral to German immigrant’s daily life. Today, much of the landscape today reflects that influence including a number of stops on the tour such as Turner Hall (1882), the Germania Building (1896) and Old St. Mary’s Church (1846). Woven between the cream city bricks, hear stories about the notable German biermeisters, tanners, merchants and artists who helped to shape Milwaukee.