Milwaukee, WI Vacation Packages

Milwaukee is the largest city in Wisconsin, making it a regional hub for everything from culture to commerce. Milwaukee is a place where 19th-century historic buildings share the same city blocks as 21st-century urban renewal projects. It is one of the beer capitals of the world, and at one time was home to the world`s four largest breweries. Today Milwaukee is famous for beer as well as its budding culinary scene, popular cultural events, and plentiful boating and water sporting activities due to its location on Lake Michigan. Moreover, Milwaukee is famous for the Milwaukee Bucks, the Brewers, some of the United States' largest breweries, and several historic and stunning landmarks.

Best Milwaukee, WI Vacation Packages:

Milwaukee to Minneapolis (Self Drive)

7 nights from $1,186*

A Road Trip adventure to the Upper Midwestern, visiting Wisconsin and Minnesota. Start in Milwaukee (with its famous breweries and Harley-Davidson's motorcycle manufacturer); then, drive to the north, and enjoy a nice stay in Door County (The "Cape Cod of the Midwest"). Don't miss the opportunity to make a stop, like many people do, at the beautiful Green Bay area, coming from Door County. After that, visit Eau Claire (famous for its Dells Mill, one of the most photographed sites in Wisconsin). Your last destination is the most populous city in Minnesota; Minneapolis (known for high-rise office buildings and a vibrant nightlife).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Customize and Book!

Other Milwaukee, WI Vacation Packages:

Lakes and Bays of Wisconsin (Milwaukee - Lake Winnebago - Green Bay - Lake Michigan - Self Drive)

8 nights from $2,226*

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Milwaukee and Door County (Self Drive)

6 nights from $1,227*

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Milwaukee and the North Lake Michigan Shore (Self Drive)

6 nights from $1,768*

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Lakes and Parks from Milwaukee to Minneapolis (Milwaukee - Madison - Eau Claire - Self Drive)

9 nights from $1,440*

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Wisconsin offer many areas to enjoy crystal water and natural landscapes. With a Rental Car discover its most popular locations; Milwaukee (largest city of Wisconsin, has advertised itself as the "City of Festivals," especially emphasizing an annual summer party along the lakefront called Summerfest); next, Lake Winnebago (Wisconsin's largest inland lake and, arguably, its most important fishery); then, Green Bay (famous for beaver pelts, paper production, and a thriving shipping industry); and finally, Lake Michigan Shore North (with a number of harbors for boat entry: Hammond Marina, East Chicago Marina and a number of others in Michigan City and Portage).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into and out of Milwaukee

Rental Car for 9 days

Hotel for 2 nights in Milwaukee

Hotel for 2 nights in Lake Winnebago

Hotel for 2 nights in Green Bay

Hotel for 2 nights in Lake Michigan Shore North

Driving Time
Milwaukee - Lake Winnebago: 1 hr. 10 mins. approx.
Lake Winnebago - Green Bay: 1 hr. approx.
Green Bay - Lake Michigan Shore North Area: 1 hr. - 1 hr. 20 mins approx.
Lake Michigan Shore North Area- Milwaukee Airport: 30 - 50 mins. approx.

8 nights from $2,226*

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Enjoy The Midwest and Great Lakes region discovering Wisconsin with this Self- Drive Package. With a Rental Car, combine and visit; Milwaukee (best known for its famous breweries and the Major League Brewers, and for the American motorcycle manufacturer, Harley-Davidson, founded there); and then, through the peninsula between Green Bay and Lake Michigan, explore Door County (a picturesque coastal town, with specialty shops and scenic beauty).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into and out of Milwaukee

Rental Car for 7 days

Hotel for 2 nights in Milwaukee

Hotel for 3 nights in Door County

Hotel for 1 night in Milwaukee

Driving Time
Milwaukee - Door County: 2 hrs. 20 mins. approx.
Door County - Milwaukee: 2 hrs. 25 mins. approx.

6 nights from $1,227*

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Have a relaxed holiday in Wisconsin State travelling between cities with a Rental-Car. Discover The Shore area of Lake Michigan, one of the Great Lakes of North America; and have a pleasant stay in the North Lake Michigan Shore (with its sand dunes, wetlands, bogs, and prairie areas offer diverse and wide camping areas as well as outdoor activities, specially in: Manitowoc, Sheboygan, Grafton and Port Washington) and Milwaukee (the largest city in the state of Wisconsin, known for its famous breweries and for the American motorcycle manufacturer, Harley-Davidson).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into and out of Milwaukee

Rental Car for 7 days

Hotel for 3 nights in Milwaukee

Hotel for 3 nights in Lake Michigan Shore North

Driving Time
Milwaukee - Lake Michigan Shore North Area: 40 mins/ 1 hr. approx.
Lake Michigan Shore South Area - Milwaukee Airport: 1.hr/ 30 mins. approx.

6 nights from $1,768*

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Have a relaxed holiday traveling between Minnesota and Wisconsin State with a Rental-Car. All cities are close to major lakes and waterways; they offer visitors the option to enjoy the outdoors or an easy access to museums and cultural activities. Discover Milwaukee (the largest city in the state of Wisconsin, known for its famous breweries and for the American motorcycle manufacturer, Harley-Davidson), Madison, Eau Claire (is the principal city of the Eau Claire, Wisconsin Metropolitan Statistical Area, famous for its Dells Mill, one of the most photographed sites in Wisconsin) and lastly, Minneapolis (a major city in Minnesota that forms "Twin Cities" with the neighboring state capital of St. Paul. Bisected by the Mississippi River).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into Milwaukee and out of Minneapolis-Saint Paul

Rental Car for 10 days

Hotel for 3 nights in Milwaukee, WI

Hotel for 2 nights in Madison, WI

Hotel for 2 nights in Eau Claire, WI

Hotel for 2 nights in Minneapolis, MN

Driving Time
Milwaukee, WI– Madison, WI: 1hrs 18 min approx.
Madison, WI- Eau Claire, WI: 1 hr 18 min approx.
Eau Claire, WI- Minneapolis, MN: 1 hrs 18 min approx.

9 nights from $1,440*

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Map of Milwaukee

Milwaukee, WI

Map of Point of Interest

Hotels and Activities

SUGGESTED Milwaukee, WI VACATION PACKAGES:

Milwaukee and Green Bay (Self Drive)

7 nights from $1,362*

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Have a relaxed holiday in Wisconsin State travelling between cities with a Rental Car. Discover Milwaukee (the largest city in the state of Wisconsin, known for its famous breweries and for the American motorcycle manufacturer, Harley-Davidson), Green Bay and Door County (a picturesque coastal town, with specialty shops and scenic beauty).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into and out of Milwaukee
Rental Car for 8 days
Hotel for 2 nights in Milwaukee
Hotel for 2 nights in Green Bay
Hotel for 2 nights in Door County
Hotel for 1 night in Milwaukee
Driving Time
Milwaukee - Green Bay : 1 hr. 50 mins. approx.
Green Bay - Door County: 1 hr. 30 mins. approx.
Door County - Milwaukee: 3 hrs. 10 mins. approx.

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Explore North Lake Michigan (Green Bay - Mackinac Straits - Traverse City - Holland -Self Drive)

10 nights from $1,616*

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A Road Trip along the shores of Lake Michigan discovering beautiful cities in Michigan and Wisconsin. Spend amazing stays in; The Lake Michigan Shore North Area (with its sand dunes, wetlands, bogs, prairie areas and wide camping areas), and Green Bay. After that, drive to Michigan and along The Mackinac Straits (witch divides two of the Great Lakes: Lake Huron and Lake Michigan). Don't miss out on the opportunity to enjoy the many recreational opportunities in the area!. Continue to Traverse City (the “Cherry Capital of the World", and home to giant sand dunes, world-class culture and arts festivals); and finish your trip in the charming town of Holland (with its Dutch heritage, white sandy beaches and downtown cobblestone sidewalks).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into Milwaukee and out of Grand Rapids
Rental Car for 11 days
Pick Up: Milwaukee Airport/Drop Off: Grand Rapids Airport
Hotel for 2 nights in Lake Michigan Shore North
Hotel for 2 nights in Green Bay
Hotel for 2 nights in Mackinac Straits
Hotel for 2 nights in Traverse City
Hotel for 2 nights in Holland
Driving Time
Milwaukee Airport - Lake Michigan Shore North Area: 30 - 50 mins. approx.
Lake Michigan Shore North Area - Green Bay: 40 mins - 1 hr. 25 mins. approx.
Green Bay - Mackinac Straits: 4 hrs. 20 mins. approx.
Mackinac Straits - Traverse City: 2 hrs. 10 mins. approx.
Traverse City - Holland: 2 hrs. 45 mins. approx.
Holland - Grand Rapids Airport: 45 mins. approx.

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Southern Wisconsin Lakeshores (Self Drive)

7 nights from $828*

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Popular southern Wisconsin offers fishing, walking and jogging paths, and hiking trails that wind throughout the parks and outdoor areas on Lake Michigan. Explore the surrounding areas with a Rental Car and visit; Lake Geneva (known as the -Newport of the West-, a popular year-round resort for wealthy Chicago residents who built summer homes and estates on the lake and in the wooded hills),Lake Michigan Shore South (with a visit to village towns like: Kenosha, Racine, or Mt. Pleasant); and Milwaukee (best known for its famous breweries and for being home to American motorcycle manufacturer Harley-Davidson). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Flight into and out of Milwaukee
Rental Car for 8 days
Pick Up/Drop Off: Milwaukee Airport
Hotel for 2 nights in Lake Geneva
Hotel for 2 nights in Lake Michigan Shore South
Hotel for 3 nights in Milwaukee
Driving Time
Milwaukee Airport - Lake Geneva: 55 mins. approx.
Lake Geneva - Lake Michigan Shore South: 55 mins. approx.
Lake Michigan Shore South - Milwaukee: 50 mins. approx.

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Milwaukee and the South Lake Michigan Shore (Self Drive)

6 nights from $1,736*

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Have a relaxed holiday in Wisconsin State travelling between cities with a Rental-Car. Discover the Shore area of Lake Michigan, one of the Great Lakes of North America; and have a pleasant stay in Milwaukee (the largest city in the state of Wisconsin, known for its famous breweries and for the American motorcycle manufacturer, Harley-Davidson) and South Lake Michigan Shore (sprawling waterfront of activity and beauty, Traveling the towns throughout the Shore you will find shopping destinations, to world-class golf courses, to family-friendly attractions and casinos).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into and out of Milwaukee
Rental Car for 7 days
Hotel for 3 nights in Milwaukee, WI
Hotel for 3 nights in Lake Michigan Shore South, WI
Driving Time
Milwaukee, WI- Lake Michigan Shore South, WI: 3 hrs. 32 mins. approx.

Customize It

Minneapolis to Milwaukee (Self Drive)

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Discover Wisconsin and Minnesota with this unique Self-Drive Package. Start in Minneapolis (the most populous city in Minnesota is known for high-rise office buildings and a vibrant nightlife). After that, drive to Eau Claire and Green Bay (a popular day trip is Door County, close to Green Bay). Then Lake Winnebago (Wisconsin's largest inland lake and, arguably, its most important fishery); and lastly Milwaukee (best known for its famous breweries and the Major League Brewers, and for the American motorcycle manufacturer, Harley-Davidson, founded there).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into Minneapolis and out of Milwaukee
Rental Car for 10 days
Hotel for 2 nights in Minneapolis
Hotel for 1 nights in Eau Claire
Hotel for 2 nights in Green Bay
Hotel for 2 nights in Lake Winnebago
Hotel for 2 nights in Milwaukee
Driving Time
Minneapolis- Eau Claire: 1 hrs. 33 mins. approx.
Eau Claire- Green Bay: 2 hrs. 59 mins. approx.
Green Bay- Lake Winnebago: 36 mins. approx.
Lake Winnebago - Milwaukee: 1 hrs. 8mins. approx.

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Lakes and Parks from Minneapolis to Milwaukee (Self Drive)

9 nights from $1,330*

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Enjoy this Self-Drive package going through Minnesota and Wisconsin, passing by its lush forests, natural landscapes and waterways with pristine waters. Visit Minneapolis (the most populous city in Minnesota, known for high-rise buildings and a vibrant nightlife). The road to your next stop is through The Badger State - Wisconsin spending pleasant stays in Eau Claire (famous for its Dells Mill, one of the most photographed sites in Wisconsin) and "America's Dairyland" Wisconsin Dells (with large urban areas, manufacturing, IT, and food products); finally, end in Milwaukee (best known for its famous breweries and for the American motorcycle manufacturer Harley-Davidson, founded there).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Included:

Flight into Minneapolis-Saint Paul and out of Milwaukee
Rental Car for 10 days
Hotel for 3 nights in Minneapolis
Hotel for 2 nights in Eau Claire
Hotel for 2 nights in Wisconsin Dells
Hotel for 2 nights in Milwaukee
Driving Time
Minneapolis - Eau Claire: 1 hr. 35 mins. approx.
Eau Claire - Wisconsin Dells: 2 hrs. approx.
Wisconsin Dells - Milwaukee: 1 hr. 50 mins. approx.

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New York City, NY
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New York City, NY

New York City, the Big Apple, is the USA's largest city. Founded as New Amsterdam, the capital of New Netherland, it became the most important city in the English colonies, and the USA`s first capital. New York City is the world capital of finance, media, and culture, and is perhaps the world`s most diverse city, where over 800 languages are spoken. There are so many layers to the city that never sleeps...you'll have to come back again and again to experience all of them. Visit and vibe with the Central Park, Statue of Liberty, Empire State Building, Times Square, Museum of Modern Art (MoMA), Metropolitan Museum of Art, Brooklyn Bridge, Rockefeller Center, The High Line, Grand Central Station, One World Trade Center, Fifth Avenue, Broadway, and so much more!
Los Angeles, CA
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Los Angeles, CA

Los Angeles is a sprawling Southern California city and the center of the nations film and television industry. Near its iconic Hollywood sign, studios such as Paramount Pictures, Universal and Warner Brothers offer behind-the-scenes tours. On Hollywood Boulevard, TCL Chinese Theatre displays celebrities' hand- and footprints, the Walk of Fame honors thousands of luminaries and vendors sell maps to stars homes. Explore the Peterson Automotive, Natural History Museum, OUE Skyspace Building, Point Dume Hiking Trail, Hollywood Walk of Fame, Disneyland, The Getty Museum, Rodeo Drive, Santa Monica Pier, Venice Boardwalk, Sunset Strip, and so much more!
Miami, FL
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Miami, FL

Miami is the largest city in South Florida and one of the largest cultural, financial, and entertainment epicenters in the United States. Known for its eclectic energy, great nightlife, art galleries and museums, delicious cuisine, and a lively Latin and Caribbean community with particularly noteworthy Cuban and Haitian enclaves, Miami is a multitude of experiences rolled into one big magic city. Explore the Vizcaya Museum and Gardens, Bayside Marketplace, Miami Seaquarium, Jungle Island, Art Deco Historic District, PortMiami, Lincoln Road, Bayfront Park, Perez Art Museum, AmericanAirlines Arena, Venetian Pool, Lummus Park, Wynwood Art District, Freedom Tower, Calle Ocho Historic District, Key Biscayne, and so much more!
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Milwaukee, WI Vacation Packages

Best Milwaukee, WI Vacation Packages:

Milwaukee to Minneapolis (Self Drive)

7 nights from $1,186*

Other Milwaukee, WI Vacation Packages:

Map of Milwaukee

Hotels and Activities

SUGGESTED Milwaukee, WI VACATION PACKAGES:

Cities in the United States