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Chicago City Breaks

Great Lakes Explorer

From €2250pp tour-only
Depart From
Chicago, Illinois
Departure Date
02 Feb 2019 - 09 Feb 2019
7 Nights
Chicago, Traverse City, Mackinac Island, Milwaukee
From €2250pp tour-only
Enquire Now

Explore Chicago, Traverse City, Mackinac Island and Milwaukee on this tour around Lakes Michigan and Huron.

Your Great Lakes Explorer tour starts in Chicago, famed for its architecture, blues clubs and deep dish pizza. See the best of the city from a photography river cruise, then take a walking tour and learn about Al Capone and the city's mob history.

Pay a visit to Kingston Mines- the largest and oldest continuously operating blues club in Chicago. See the Dutch heritage in the town of Holland, on the shore of Lake Michigan.

Visit some of the Leelaau Peninsula's noted wineries, then spend the evening in the retro and charming Traverse City. 

Take the ferry to the charming Mackinac Island, where bicycles and horse-drawn carriages are the only means of transportation. Cycle around the island's coastline route and take in the dramatic forestry and rocky shores of Lakes Michigan and Huron.

Boosted  by glacier-rich soil, Michigan is a brewer's paradise, with countless microbreweries and brewpubs. Taste some of the local craft beers before taking a ferry to cross into Wisconsin state.

Milwaukee's Public Market is a bustling downtown food destination, bursting with high quality artisan and ethnic foods. This cosmopolitan city boasts lots to see and do, including the beautiful Riverwalk, art museum, North Point Lighthouse, Miller Park and City Hall.

Visit the Harley Davidson museum and learn the story of the history and culture of this iconic brand. On your final night, you'll enjoy dinner at a Bavarian Bierhaus offering both German and local brews. 

Finally, pay a visit to the home of famous architect Frank Lloyd Wright then see the birthplace of Ernest Hemingway.

Make your way to Chicago airport for your homeward flight, or begin the second leg of your holiday. Should you wish to extend your stay, please ask us about booking accommodation in Chicago or elsewhere in the United States.

Sightseeing includes:

  • Chicago Loop
  • Holland, Traverse City
  • Mackinac Island
  • Milwaukee
  • Oak Park
  • Leelanau Peninsula
  • Milwaukee Public Market
  • Harley Davidson Museum
  • Frank Lloyd Wright Home & Studio

Experiences include:

  • Chicago Architecture Photography River Cruise
  • Chicago Sin & Suds walking tour or City Segway tour
  • Night at Kingston Mines Blues Club
  • Winery tour & tasting
  • Half-day Bicycle for self-guided tour OR Horse & Carriage tour
  • Craft Brewery tasting, Bavarian Beer Garden

DAY 1 Chicago

This evening, mingle with other group members at a meet and greet reception hosted by our Tour Manager, a destination specialist.

DAY 2 Chicago

Chicago, situated on Lake Michigan, is among the largest cities in the U.S and is famed around the world for many things, including its bold architecture, blues musicians and clubs, deepdish pizza - and Al Capone.

There’s no better way to tour Chi-town, as it’s called, than on the Chicago Architecture Foundation’s architectural River Cruise. But we won’t take the ordinary river tour. We’ll board an exclusive CAF photography river cruise, designed for the photographer, or photographer at heart. You’ll have access to all angles while the local, highly-trained docent points out architectural highlights along the way.

This afternoon, choose between excursions. If you like sin with your suds, then join our walking tour and learn the basics of Chicago’s sinful history, all the way from the city’s first vice district, to Capone, Prohibition and the mob.

Explore the basics of different beer styles and beer’s influence on criminal enterprises, especially during Prohibition. You’ll taste several Midwestern craft beers from lagers to porters

Or,  choose to glide along the Lakefront on your very own Segway, through the fragrant floral paths and rose gardens of Grant Park to the Museum Campus If you can stand you can learn to use a Segway. Knowledgeable guides explain the culture and history of the area and massive museums.

Tonight, Kingston Mines is on the menu. Founded in 1968, Kingston Mines is the largest and oldest continuously operating blues club in Chicago. Its two stages have been graced by the likes of Magic Slim, Billy Branch, Junior Wells and scores of other musical greats.

We’ll listen to some of Chicago’s best live music – and remember their motto: “Hear Blues – Drink Booze – Talk Loud – You’re Among Friends!” ™ You may want to eat before we go, or save your appetite for the southern style fare you can get onsite from Doc’s Rib Joint.

DAY 3 Chicago- Holland- Traverse City

You won’t need your passport to enter this Holland, on the shore of Lake Michigan. The Dutch heritage is plain to see in the traditional Dutch architecture and ambiance. Stroll the quaint downtown and enjoy its galleries, shops and eateries. We’ll continue north to the Leelanau Peninsula.

Here we visit some of the peninsulas noted wineries. We’ll discover breathtaking views and stylish wines as well as their passionate winemakers. The evening is spent in Traverse City. The downtown exudes retro charm with plenty of fresh, farm to table restaurants and big-city entertainment with a small-town feel. You may want to take in a show, the opera or live jazz.

DAY 4 Traverse City- Mackinac Island

We leave our vehicle behind and board the ferry to Mackinac Island. This Victorian-style island, covering only 3.8 square miles (9.8 km2) in land area, is located in Lake Huron, at the eastern end of the Straits of Mackinac, between the state's Upper and Lower Peninsulas.

The entire island is listed as a National Historic Landmark and is well known for its wide variety of architectural styles, including the Victorian Grand Hotel and its ban on all motor vehicles.

Day 5 Mackinac Island

This morning, as part of the included touring, you can explore Mackinac Island your way. Bicycles and horse-drawn carriages are the only modes of transportation here. You can pick up a bicycle- or adult tricycle- and gear, along with trail maps guiding you on various routes throughout the island. Take the perimeter route to loop around Mackinac Island’s shoreline.

The flat, smooth asphalt road places you right between dramatic forestry and the rocky shores of Lake Michigan and Lake Huron with majestic views of their deep blue waters. Or take a more adventurous tour route for an “immersive experience” to see Mackinac Island’s points of interest such as Skull Cave, the Grand Golf Course, Arch Rock, Governor's Residence and Fort Mackinac.

You may want to sit back and relax on a guided horse-drawn carriage instead. See many of the island’s sites with stops along the way. The afternoon and evening is free to enjoy as you like.

Day 6 Mackinac Island- Lake Michigan Crossing- Milwaukee

Heading south today, we’ll stop to taste some of the local craft beers. Bolstered by the Great Lakes and nurtured by the glacier rich soil, Michigan is a brewer's paradise with countless varieties of styles and tastes. It ranks fifth in the nation in the number of breweries, microbreweries and brewpubs.

Late afternoon we make the ferry crossing across Lake Michigan to Wisconsin. Tonight we visit Milwaukee's most unique downtown food destination, the Milwaukee Public Market.

Bursting with unique, high quality selections of artisan and ethnic products, and freshly -prepared foods, you’ll have a wide variety of dinner options from its independent merchants. Enjoy your selection in the Market’s Palm Garden.

Day 7 Milwaukee

Once known almost exclusively as a brewing powerhouse, the city now boasts the beautiful Milwaukee Riverwalk and Milwaukee Art Museum, with its architecturally impressive addition shaped like a floating cross, with wings opening and closing from a central base

This morning we’ll tour past the elegant mansions along Lake Michigan with numerous photo opportunities at the city’s most unique landmarks, as well as several stops where you can interact with locals and experience the city as they do. We’ll take in City Hall, the Milwaukee Art Museum, North Point Lighthouse, Miller Park, the Historic Third Ward and much more.

This afternoon we’ll visit the Harley Davidson Museum. “It’s the best of American design and culture – seasoned with freedom and rebellion, showcased in a landmark building.” Exhibits tell the stories of the extraordinary people, products, history and culture of Harley-Davidson and for some of you, this is the moment you've been waiting for. That's right, go ahead and swing your leg over one of the many motorcycles that inhabit the gallery.

We’ll enjoy a final night dinner together at a Bavarian Bierhaus. Enjoy Bavarian favorites from jaegerschnitzel to bienenstich and both local and German style beers from its own brewery. Milwaukee’s German heritage is apparent throughout the city and in its beer gardens

Day 8 Milwaukee- Oak Park- Chicago

After departing Milwaukee we arrive in Oak Park, once the home of Frank Lloyd Wright where he designed and built some of his earliest buildings. Unity Temple and Wright's own former home and studio are among the many Wright buildings still preserved in the village. We’ll tour the Wright home and see the birthplace of Ernest Hemingway before time for lunch in the village.

Chicago: Palmer House Hilton

Traverse City: Sugar Beach/ Grand Beach

Mackinac Island: Island House Hotel

Milwaukee: Aloft Downtown

*similar hotels may be substituted on specific dates

Price is based on two adults sharing and includes:

  • 7 nights accommodation
  • Meals:
    • Welcome Reception
    • 1 Lunch
    • 1 Dinner
  • Transportation via air-conditioned small coach, sprinter or van
  • Professional Tour Manager
  • Mackinac Island Ferry
  • Lake Michigan Ferry
  • Sightseeing as outlined in itinerary
  • Experiences  as outlined in itinerary

Please ask us about adding great value:

  • International flights- we'll find the best value fares for your chosen dates
  • Travel insurance
Subject to availability. Terms & conditions apply.

For more information please call us on 021 427 7094 or 01 696 5135, email info@shandontravel.ie, request a call back using the red button or submit an enquiry through the form below.

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