Chicago boat tour. Credit: Jason Lindsey
Chicago boat tour. Credit: Jason Lindsey
Chicago skyline (left), Scratch Brewery (middle), and cycling along Lake Michigan, credit: Adam Alexander (right)
Chicago skyline (left), Scratch Brewery (middle), and cycling along Lake Michigan, credit: Adam Alexander (right)
Mackinac shoreline (left), and Big Sable Point lighthouse along Lake Michigan
Mackinac shoreline (left), and Big Sable Point lighthouse along Lake Michigan

Great Lakes Explorer - Small Group Tour

7 nights from €2,669 per person Including Flights


This is a lovely escorted tour for the discerning traveller who is looking for an authentic experience and enjoy local cuisines, wines and beers, whilst exploring the Great Lakes region with its beautiful landscapes and vibrant cities. There will be a maximum group size of twenty and with plenty of different excursions to choose from, you can enjoy your holiday at your own pace. You’ll also be staying in each place for two nights (apart from one night in Traverse City, MI) giving you more time to relax. (TourMappers)


  • In Chicago take a river cruise, and either a walking tour or a Segway tour
  • Enjoy a night at the renowned Kingston Mines Blues Club
  • Tour and Taste at both a winery and a craft brewery
  • Relax for a couple of nights on the quaint motor-free island of Mackinac

Itinerary Overview

Fly into Chicago 2 nights – Mackinac Island 2 nights – Traverse City 1 night – Milwaukee 2 nights – Fly home from Chicago

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
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  • Choice of airlines and the option to switch
  • A friendly, family run business with a wealth of experience.
  • Great deals on offer for multiple destinations
  • No amendment fees
  • Low deposits
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Day 1


Fly to Chicago and transfer independently to the hotel. This evening enjoy a welcome reception hosted by the Tour Manager to meet your fellow travellers and enjoy an introduction to the tour ahead.

Overnight: Palmer House Hilton, Chicago

Day 2


Chicago, situated on Lake Michigan, is known around the world for many things, including its bold architecture, blues music and deep-dish pizza. There’s no better way to see the city than on the Chicago Architecture Foundation’s architectural River Cruise. This cruise is designed with photo opportunities in mind and you’ll have access to all angles while the local guide points out architectural highlights along the way. In the afternoon you have a choice of excursions including a walking tour to learn about the sinful past of the city, from Al Capone and the mob to Prohibition, including some craft beer tasting en route. Alternatively take a Segway tour along the lakefront along the floral paths and rose gardens of Grant Park to the Museum Campus. Tonight there is a visit to the largest and oldest blues club in Chicago, to listen to fantastic live music. You may want to eat before you go, as their motto is “Hear Blues, Drink Booze, Talk Loud, You’re Among Friends” !

Overnight: Palmer House Hilton, Chicago

Day 3

Chicago – Holland – Mackinac Island (413 miles)

Bid farewell to Chicago and head for the beaches of Holland on the shores of Lake Michigan. Stroll through this delightful town with its strong Dutch heritage displayed in the architecture, canals and authentic Dutch windmill.

Continue to Mackinaw City, where you will leave the vehicle behind and board the ferry to Mackinac Island. Located on Lake Huron, this island measures less than 4 square miles and is listed as a National Historic Landmark, with all motor vehicles banned. You will spend two nights here, giving you chance to explore and enjoy this gem of an island.

Overnight: Lake View Hotel, Mackinac Island

Day 4

Mackinac Island

This morning you can choose from two options that are included in the price, so 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.

Overnight: Lake View Hotel, Mackinac Island

Day 5

Mackinac Island— Leelanau Peninsula—Traverse City (102 miles)

Enjoy a relaxed start on the island with some more free time, before boarding the ferry back to the mainland. Today you’ll be heading south into Michigan to Traverse City, but first stop on the Leelanau Peninsula. Here you’ll enjoy visits to some of the peninsulas noted wineries, admire the breathtaking views and taste the delicious wines from these passionate winemakers.

Then continue onto spend the evening in Traverse City. The downtown of this city exudes retro charm with a great choice of farm to table restaurants and big-city entertainment with a small-town feel.

Overnight: Hotel Indigo Traverse City

Day 6

Traverse City – Lake Michigan Crossing - Milwaukee (251 miles)

Continue south, pausing on the way to taste some local craft beers. Michigan ranks fifth in terms of number of breweries and brewpubs and the state is famed for the countless varieties of styles and tastes. Today you will enjoy an included lunch, before you cross Lake Michigan by ferry into Wisconsin. Tonight you will visit Milwaukee’s unique 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.

Overnight: Aloft Downtown Milwaukee

Day 7


Known as a brewing powerhouse, Milwaukee also boasts the beautiful Milwaukee Riverwalk and Milwaukee Art Museum, with its architecturally impressive addition shaped like a floating cross. This morning tour past the elegant mansions along Lake Michigan with numerous photo opportunities of the city’s most unique landmarks, as well as several stops where you can interact with locals and experience the city as they do. Take in City Hall, the Milwaukee Art Museum, North Point Lighthouse, Miller Park, the Historic Third Ward and much more.

This afternoon visit the Harley Davidson Museum where exhibits tell the stories of the extraordinary people, products, history and culture of Harley-Davidson. Tonight you’ll enjoy a final night dinner all together at a Bavarian Bierhaus. Enjoy Bavarian favourites 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.

Overnight: Aloft Downtown Milwaukee

Day 8

Milwaukee – Oak Park – Chicago (150 miles)

Leave Milwaukee and drive to 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. Tour the Wright home and see the birth-place of Ernest Hemingway before time for lunch in the village. Then early afternoon you can either be dropped off at Chicago’s O’Hare airport for your flight home or return to downtown Chicago for another night or two.

  • International flights
  • Transportation on air-conditioned small coach or Sprinter van, also Mackinac Island Ferry and Lake Michigan ferry
  • 7 nights hotel accommodation described above or similar
  • 1 lunch and 1 dinner
  • Sightseeing and excursions as described above
  • Tour Manager throughout

Brendan White
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