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Lake Michigan, USA

Highlights of the Great Lakes

14-day tailor-made self-drive from £2,880 pp


Short description

Watch as sweeping shorelines, architectural icons and powerhouse cities combine


  • Experience some of America’s favourite getaways with scenic coastal drives past picturesque villages and historic lighthouses
  • Get onto the lakes themselves with trips to islet wildernesses and Mackinac Island, where cars have been banned since 1898
  • See the region’s great cities with Chicago’s sights, Milwaukee’s brewing and Minneapolis, where you’ll stay on the Mississippi itself

In Brief

  • 1 Night Chicago
  • 2 Nights Door County
  • 1 Night Spring Green
  • 1 Night Winona
  • 1 Night St Paul
  • 2 Nights Bayfield
  • 1 Night Marquette
  • 2 Nights Mackinac County
  • 1 Night Saugatuck


Recommended for:
Activity adventure | Natural world | Self-drive

The Great Lakes are a favourite American getaway destination, inspiring such great minds as Hemingway, Dylan and Vonnegut. On this two-week road trip you’ll start in Chicago as acres of cornfields and craggy coasts knit together the region’s great cities, including Milwaukee and Minneapolis, where you’ll stay on the Mississippi River itself. Heading onto the lakes will bring you to picturesque islands whose laneways are plied only by horses and bicycles and Bayfield’s rugged islet wildernesses, best explored by kayak. 

Day by day itinerary

Day 1

Flying into Chicago, an architectural showcase on the shores of Lake Michigan, a private transfer will see you to your central accommodation. Then, between indulging with its Michelin-starred restaurants and deep-dish pizza, you'll have the opportunity to take in the Windy City's myriad sights. There's everything from the superb Art Institute of Chicago and the start of Route 66 to the citywide views of the 360 Observation Desk and the world-class shopping at Magnificent Mile. Alternatively, simply take a walk among  the attractions of Navy Pier or follow the coast further down to Millennium Park, a collection of new-age art sculptures.

Stay: Raffaelo (Superior)

Days 2-3
Door County

Pick up your car on day two and start your drive to the picturesque villages, fruit farms and lighthouses that dot Door County’s craggy coastline. On the way, you’ll visit Milwaukee; once known exclusively as a brewing powerhouse it now features scenic river walks and Milwaukee Art Museum. Even those who’ve never opened a choke will appreciate the Harley Davidson museum.

You’ll then arrive in Door County itself, the ‘Cape Cod of the Midwest’. With five state parks, ten lighthouses and over 300 miles of shoreline, this 75-mile long peninsula was named one of the top ten vacation destinations in North America. Spend the next two nights in a quaint village where shops and galleries are set in century-old barns, rustic log cabins and vintage homes.

Stay: Eagle Harbor Inn, Ephraim, Wisconsin (Superior)

Day 4
Spring Green

Travel west to Spring Green, visiting Baraboo en route. Home to the Circus World Museum, it’s the former headquarters and winter home of the Ringling Brothers Circus. Now it’s the largest library of circus information in America.

Stay: Fairfield Inn & Suites Madison West, Middleton (Standard)

Day 5
Spring Green/Winona

This morning, visit two of Spring Green’s finest attractions. Frank Lloyd Wright, one of America’s finest architects, called the region home, building a spectacular architectural school at Taliesin that’s now open up to tours. It’s only matched by Alex Jordan’s House on the Rock; built in 1959 atop a rock column, it features the world’s largest carousel and interiors covered in unique artwork and contraptions. In the afternoon, you’ll continue on to Winona.

Stay: Winona Alexander Mansion (Deluxe)

Meals: Breakfast included

Day 6
Minneapolis/St. Paul

Follow the banks of the Mississippi River to Minneapolis and St. Pauls, two twin cities pretty much on top of each other. Walk the latter’s river trails, visit the historic Riverfront District or shop the day away at the Mall of America in neighbouring Bloomington. Your accommodation tonight is aboard a restored tugboat on the Mississippi itself.

Stay: Millennium Hotel Minneapolis (Superior)

Meals: Breakfast included

Days 7-8

Bayfield is a small Victorian town whose hilly streets and orchards act as the gateway to the Apostle Islands National Lakeshore, a national park that encompasses 21 wilderness islands and over 12 miles of scenic peninsula shoreline. Set in Lake Superior’s western corner, the region is widely regarded as having the nation’s finest collection of historic lighthouses and with good reason. The Apostle Islands are rugged and windswept making for excellent kayaking and scenic boat trips with hiking equally popular.

Stay: Bayfield Rittenhouse Inn (Superior)

Meals: Breakfast included

Day 9

Cross the Upper Peninsula to Marquette, bordered to its north by Lake Superior and by Lake Michigan and Lake Huron to its southeast. Its extensive stretch of Great Lakes coastline features large tracts of state and national forest, cedar swamps, waterfalls and an almost European and Scandinavian feel. In local restaurants you’ll find the pasty, beloved by Cornish miners, and juustoa, a squeaky cheese brought to the US by the Finnish.

Stay: Marquette Landmark Inn (Superior)

Days 10-11
Mackinac Island

Drive onwards to St Igace to take the 20-minute passenger ferry to Mackinac islands where bicycles and horse drawn carriages are still the preferred modes of transport with cars banned since 1898. Explore on foot with a self-guided hike, rent a bicycle or just relax and enjoy the beauty of this charming island where 80% is state parkland. 

Stay: Grand Hotel, Mackinac Island, Michigan (Superior)

Day 12

Head back to the mainland and continue to Saugatuck, one of Michigan’s favourite beachside towns. Here you’ll find a lively atmosphere complete with festivals and a range of outdoor recreation, including fishing, golf and boat cruises. You’ll also enjoy its thriving arts community evident in galleries and boutiques, all on the shores of Lake Michigan.

Stay: Saugatuck Beachway Resort & Hotel (Superior)

Day 13
Depart for UK

Return to Chicago to drop off your hire car and board your overnight flight back to the UK.

Day 14
Arrive UK

Arriving back in the UK, continue your journey home.



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Standard Superior Deluxe

14-day tailor-made self-drive
from £2,880 pp

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Upgrade (Day 1) The Peninsula Hotel


Start your trip with a stay in one of Chicago’s best-regarded hotels; the Peninsula has consistently been awarded the Forbes Five Star and AAA Five Diamond awards year on year.

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0636 to discuss how we can tailor your holiday.

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