
Embark on a remarkable 16-night adventure through the heart of North America’s freshwater wonderland. Beginning in Chicago, you’ll follow the shores of Lakes Michigan, Superior, Huron, Erie and Ontario — discovering lively cities, peaceful islands and breathtaking lakefront scenery along the way. Visit Milwaukee, birthplace of Harley-Davidson®; stand on the rugged shores of Lake Superior in Marquette; and cross into Canada to explore the rich landscapes and lake views of Ontario.
Your journey continues through the peaceful beauty of Manitoulin Island and the Blue Mountains before reaching Toronto’s iconic skyline and magnificent Niagara Falls, where the thunderous Horseshoe Falls offers a spectacular natural highlight. Then travel through the picturesque Finger Lakes region to finish in New York City for two vibrant nights in the Big Apple. This is a road trip that blends grand landscapes with world-class cities — an unforgettable loop through the Great Lakes and beyond.
Remember: We’re UK-based, and every holiday we create is fully flexible – you can add nights, upgrade hotels, or enhance your itinerary. We love designing tailor-made self-drive adventures just for you!
Explore All Five Great Lakes in one epic journey.
Marvel at Niagara Falls: Stay on the Canadian side overlooking the astonishing Horseshoe Falls.
Enjoy time in Chicago, Toronto and New York City on one incredible route.
Relax on Manitoulin Island surrounded by forests, lakes and island culture.


Arrive in Chicago and settle in for three unforgettable nights in this lively Great Lakes metropolis. Explore architectural icons such as the Willis Tower Skydeck and 360 Chicago, stroll through Millennium Park to see “The Bean,” or enjoy a scenic walk along the Lakefront Trail. Food lovers can savour everything from deep-dish pizza to gourmet dining, while museum enthusiasts will appreciate the Art Institute of Chicago, home to world-renowned collections. Cruise the Chicago River on an architectural boat tour to learn about the city’s pioneering skyscrapers, or wander Navy Pier at sunset for classic Midwestern lake views.
3 Nights in
Chicago, IL
Arrive &
Explore

Follow the scenic shoreline of Lake Michigan north to Milwaukee, a friendly lakeside city with rich cultural heritage. Visit the Harley-Davidson® Museum, showcasing more than a century of American motorcycle history, or tour the historic Miller Brewery, a staple of Midwestern tradition. Wander along the revitalised RiverWalk, lined with cafés and public art, or explore the impressive Milwaukee Art Museum, famous for its striking, wing-like architectural design. With beautiful waterfront parks and a relaxed atmosphere, Milwaukee offers a comfortable and welcoming stop on your Great Lakes journey.
1 Night in
Milwaukee, WI
95 miles

Continue into Michigan’s Upper Peninsula, passing through Green Bay before reaching Marquette, a charming town framed by forests, rocky coves and the immense waters of Lake Superior. Take in vast lake views from Presque Isle Park, walk lakeside trails, or explore the region’s mining history at the Michigan Iron Industry Museum. Marquette’s vibrant arts scene, historic red-sandstone buildings and cool northern atmosphere make it a refreshing contrast to the urban feel of earlier stops — and a perfect base for enjoying the wild beauty of this Great Lake.
1 Night in
Marquette, MI
290 miles

Follow the scenic coastline of Lake Superior toward Sault Ste. Marie, where the U.S. and Canadian cities share the same name across the St. Marys River. Cross the border into Canada and explore the historic Soo Locks, one of the world’s busiest and most impressive engineering waterways. Discover the city’s waterfront parks, museums and local dining, or take a stroll through the compact downtown area. With Indigenous history, maritime heritage and lakefront viewpoints, this border city offers a fascinating transition between the two countries on your route.
1 Night in
Sault Ste. Marie, ON
165 miles

Travel around Lake Huron to reach Manitoulin Island, the world’s largest freshwater island and a peaceful two-night retreat. The island is known for its serene landscapes, turquoise coves and more than 100 inland lakes, including beautiful Lake Manitou. Enjoy hikes along quiet forest trails, swim in crystal-clear waters, or visit local art galleries and cultural centres celebrating the region’s strong Indigenous heritage. Charming towns like Little Current and Kagawong add character, while the island’s dramatic white cliffs and slow pace make it ideal for unwinding amid pure natural beauty.
3 Nights on
Manitoulin Island, ON
215 miles

Depart Manitoulin Island via the scenic ferry crossing, enjoying sweeping lake views as you travel. Continue toward the Blue Mountains, a popular four-season resort area overlooking Georgian Bay, part of Lake Huron. Explore the pedestrian village, enjoy gentle hikes through wooded trails, or ride the open-air gondola for panoramic bay vistas. The region is also home to local cideries, beaches and quiet harbours — making it a picturesque stop filled with fresh air, natural scenery and relaxed outdoor activities.
1 Night at
The Blue Mountains, ON
Ferry +
140 miles

Arrive in Toronto, a bustling multicultural city set along Lake Ontario. Head up the CN Tower for sweeping panoramic views, explore historic Casa Loma, or spend time along the lively waterfront. Wander through the shopping mecca of the Eaton Centre, savour global cuisine in Kensington Market, or visit the Royal Ontario Museum to learn about culture, art and natural history. Toronto’s energetic streets, iconic skyline and world-class dining make it one of North America’s most dynamic and exciting cities.
2 Nights in
Toronto, ON
110 miles

Drive south to Niagara Falls, where the thunder of the Horseshoe Falls greets you long before you see them. Stay on the Canadian side for the best views, with your hotel overlooking the sweeping curtain of water. Step aboard the famous Maid of the Mist or Hornblower boat for an exhilarating trip into the mist, or explore the scenic promenade and observation points. Optional attractions include the Journey Behind the Falls tunnels, Clifton Hill entertainment district and scenic drives along the Niagara Parkway.
1 Night in
Niagara Falls, ON
80 miles

Cross back into the USA and enjoy views of Lake Erie as you pass through Buffalo, then continue toward the tranquil Finger Lakes. Base yourself in Ithaca, known for its vibrant college-town energy and stunning natural scenery. Explore beautiful gorges and waterfalls in Watkins Glen State Park or Taughannock Falls State Park, sample award-winning local wines along scenic lake roads, or visit picturesque towns like Skaneateles. With its mix of outdoor adventures, charming villages and regional flavours, the Finger Lakes offers a restful and inspiring two-night stay.
2 Nights at
The Finger Lakes, NY
165 miles

Arrive in New York City for the final two nights of your Great Lakes journey. Drop your car off and explore classic sights such as the Statue of Liberty, Times Square, Central Park, the Empire State Building, and the 9/11 Memorial & Museum. Wander through neighbourhoods like SoHo, Greenwich Village or Chinatown, enjoy world-class dining, or catch a Broadway show. New York’s electric atmosphere provides a thrilling contrast to the peaceful lakes and landscapes earlier in your trip. On your final morning, enjoy one last coffee in Manhattan before flying back to the UK — ending your adventure on a true high note.
2 Nights in
New York, NY
230 miles

Our team have travelled extensively across the USA & Canada to ensure that they can give first hand, unrivalled experience when discussing our holidays.
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