Discover the very best of the Great Lakes region on this unforgettable multi-destination journey through the heart of North America. From the architectural splendour of Chicago to the lakefront charm of Milwaukee and Green Bay, this itinerary blends vibrant city experiences with scenic drives and fascinating history. Cross into Michigan to explore the tranquil beauty of St. Ignace and the cultural energy of Detroit, before heading into Canada to enjoy cosmopolitan Toronto and the awe-inspiring Niagara Falls. Your adventure concludes in Cleveland, Ohio, a city rich in music, culture, and warm Midwestern hospitality.
To help you make the most of your trip, we’ve included four fantastic experiences: Hop-on-Hop-off sightseeing tours in both Chicago and Toronto, giving you the freedom to explore at your own pace; a Best of Niagara Falls Tour, featuring iconic views and an unforgettable boat cruise; and admission to the Rock & Roll Hall of Fame in Cleveland, where music history comes to life. Perfectly balanced between urban discovery, natural wonders, and cultural highlights, this Great Lakes holiday offers an enriching journey you’ll never forget.
All of our itineraries are fully customisable and can be tailored to suit your individual preferences. Whether you’d like to start or end in a different city, upgrade your hotel accommodation, or add sightseeing excursions to enrich your experience, your Discover North America Travel Specialist is here to help.
This itinerary can also operate in reverse, starting in Cleveland and ending in Chicago. Your Travel Specialist will be happy to tailor the route and travel arrangements to suit your preferred direction of travel, flight options, or schedule.
We don’t include international flights in our headline prices as standard, as we work with a wide range of scheduled airline partners and offer flexible options to suit your preferences. Factors such as departure airport, airline, travel class, travel dates, and seasonal promotions can all impact the final fare. Your Discover North America Travel Specialist will take the time to understand your individual requirements and source the best-value flights tailored to your itinerary.
Find out more about the process we follow here.
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Welcome to Chicago. Among one of the largest cities in the U.S., Chicago’s unique blend of stunning architecture, attractions and local charm makes it an unforgettable destination. Upon arrival, transfer independently to your hotel. Overnight in Chicago.
With one full day to explore Chicago, the included hop-on-hop-off sightseeing bus tour offers the perfect way to experience the city’s most iconic attractions at your own pace. Begin your day with panoramic views from the Skydeck at Willis Tower or 360 CHICAGO Observation Deck, where you can take in the city’s stunning skyline and Lake Michigan. Hop off near Millennium Park to snap a photo with the famous “Cloud Gate” sculpture — affectionately known as The Bean — and enjoy a stroll through the park’s gardens and art installations. Continue to the Magnificent Mile for world-class shopping and dining, then visit the Art Institute of Chicago, home to one of the finest collections of Impressionist and American art in the world. In the afternoon, consider a river cruise to admire Chicago’s legendary architecture from the water, or simply relax along the scenic Riverwalk with a coffee or cocktail in hand. As evening falls, enjoy dinner in one of Chicago’s renowned restaurants — perhaps sampling the city’s famous deep-dish pizza — before soaking up the lively atmosphere of this vibrant, world-class city.
This morning, pick up your rental car and head north to Wisconsin’s largest city, Milwaukee. Just 90 miles from Chicago, this friendly Midwestern city is a combination of cherished tradition and modern attitude. Built along the lakefront of Lake Michigan with the Milwaukee River weaving through downtown, excursion boats and kayaks beckon one to get out on the water. Experience the city’s brewing heritage with a brewery tour, or explore one-of-a-kind attractions like the Milwaukee Art Museum, Miller Park and the world’s only Harley-Davidson Museum. Overnight in Milwaukee.
Today it’s on to Green Bay, Wisconsin’s oldest community. With Lake Michigan serving as the city’s north border, Green Bay is defined by its natural surroundings. Explore nature while learning the importance of preserving natural landscapes with a visit to Bay Beach Wildlife Sanctuary. Railway buffs will be in seventh heaven when visiting the National Railroad Museum, one of the oldest and largest museums dedicated to the country’s rich railroad heritage. And for those with a passion for NFL football, a visit to the Green Bay Packer’s Hall of Fame at Lambeau Field is a must. Overnight in Green Bay.
Offering stunning views of the shoreline, today’s scenic drive along the northwestern coast of Lake Michigan takes you through Hiawatha National Forest and Manistique en route to St. Ignace. Known as the “Gateway to the Upper Pen- insula”, St. Ignace is where the great waters of Lake Huron and Lake Michigan meet. Enjoy a stroll along the Huron Boardwalk for a taste of pure Michigan, and savour a slower, simpler lifestyle in this area filled with blue waters, green forests and incredible places of discovery. Overnight in St. Ignace.
Take a ferry to the timeless resort island of Mackinac - the jewel of the Great Lakes - where cars are prohibited, and bicycles and horse- drawn carriages rule the roads. Visit Fort Mackinac, located on a bluff overlooking the entrancing Straits of Mackinac, and enjoy the view from the porch of the Grand Hotel. Drive your own buggy along the shoreline, or rent a bike and explore over 70 miles of natural and paved trails. Whatever you choose, the beauty and history of Mackinac will captivate you. Return to St. Ignace in the late afternoon. Overnight in St. Ignace.
Crossing the Mackinac Bridge that connects Michigan’s Upper and Lower Peninsula over the Straits of Mackinac, make your way south through Petoskey, one of the most beautiful regions in the state, and Charlevoix, to the Cherry Capital of the U.S - Traverse City. From here it’s on to the “Motor City.” Once known as the “Paris of the West,” Detroit acquired the nickname “Motor City” as a result of its longstanding recognition as the historic heart of the American automotive industry. Overnight in Detroit.
Whether you want to spend your day inside at a museum or play all day on the lake, there’s plenty of things to do in Detroit. At the Ford Piquette Avenue Plant, visitors have the opportunity to take a step back in time and gain a first-hand look at the birthplace of the 1909 Model T automobile. At The Henry Ford, you’ll discover America - its culture, inventions, people and can-do spirit. There’s also a Riverwalk, awesome art galleries, Motown’s first recording studio, beautiful beaches, shopping meccas and dining to die for. Overnight in Detroit.
Today, crossing the U.S./Canada border into Ontario, your destination is Toronto. The capital of Ontario and the country’s largest city, Toronto sits at the tip of Lake Ontario, the most eastern of the Great Lakes. Home to a dynamic mix of attractions - from museums and galleries to the world famous CN Tower and, just off shore, Toronto Islands - Toronto has everything you would expect from a world class city. Overnight in Toronto.
With one full day to explore Toronto, the included hop-on-hop-off sightseeing bus provides the ideal way to discover the city’s highlights at your own pace. Begin your adventure at the CN Tower, Toronto’s most recognisable landmark, where you can take in sweeping views of the skyline and Lake Ontario from its glass-floored observation deck. Hop off at the Harbourfront Centre to enjoy a stroll along the waterfront or take a short boat cruise to the Toronto Islands for picturesque views back toward the city. Continue your journey through Toronto’s diverse neighbourhoods — from the historic charm of the Distillery District, with its cobblestone streets and boutique shops, to the vibrant energy of Kensington Market, known for its eclectic mix of cafés and street art. Art lovers can visit the Art Gallery of Ontario, while sports fans may wish to stop at the Hockey Hall of Fame. In the evening, dine in the Entertainment District, where world-class restaurants, live theatre, and rooftop bars showcase Toronto’s cosmopolitan flair — the perfect way to end your day in one of Canada’s most exciting cities.
Just an hour and a half’s drive from Toronto, one of the Seven Natural Wonders of the World awaits — the spectacular Niagara Falls. The journey itself is a highlight, following a scenic route through Ontario’s wine country and along the Niagara Parkway, often described by Winston Churchill as “the prettiest Sunday afternoon drive in the world.”
Before reaching the falls, we recommend a stop in the charming town of Niagara-on-the-Lake, a beautifully preserved 19th-century community filled with boutique shops, heritage buildings, and floral-lined streets. It’s also at the heart of Ontario’s wine region, where travellers can visit one of the many local vineyards for a tasting of the area’s famous ice wine or enjoy lunch at a winery restaurant overlooking rolling vineyards.
Upon arrival into Niagara Falls, check into your hotel and in the evening get a different view of the Falls with the nightly illumination and seasonal fireworks. Overnight in Niagara Falls.
Today, experience the very best of Niagara Falls on a fully guided Best of Niagara Falls Tour, showcasing the region’s most iconic sights and unforgettable experiences. This four-hour adventure begins with a thrilling boat cruise aboard Hornblower Niagara Cruises (seasonal), where you’ll sail right into the mist for a breathtaking, up-close view of the mighty Horseshoe Falls. Next, ascend to the Skylon Tower Observation Deck for sweeping panoramic views of the Falls, the Niagara River, and the surrounding landscape. You’ll also visit Journey Behind the Falls, where a series of cave-like tunnels lead you to observation decks just steps from the thunderous curtain of water — an exhilarating and humbling perspective of this natural wonder.
The tour also includes a scenic narrated drive through the Niagara region, highlighting several fascinating points of interest such as Dufferin Islands, the International Control Dam, the Old Scow, Whirlpool Rapids, and the famous Floral Clock. With expert commentary bringing each stop to life, this immersive experience is the perfect way to see, hear, and feel the incredible power and beauty of Niagara Falls.
Today, you’ll depart Niagara Falls, Ontario, and journey southwest across the U.S. border into Cleveland, Ohio — a scenic drive of around four to five hours, depending on your chosen route and stops along the way. As you leave the Falls behind, follow the shoreline of Lake Erie, where you might pause in Erie, Pennsylvania, to stretch your legs with a lakeside stroll or visit Presque Isle State Park, known for its sandy beaches and picturesque lighthouse.
As you approach Ohio, consider a stop in Ashtabula County, home to rolling vineyards and historic covered bridges — perfect for a scenic photo opportunity or a leisurely lunch. Upon arriving in Cleveland, you’ll return your rental vehicle and check into your Downtown hotel, ideally situated for exploring the city’s vibrant restaurants, entertainment districts, and waterfront. This evening, unwind and enjoy a relaxed introduction to the city — perhaps a casual dinner in the Historic Warehouse District or a waterfront drink overlooking the shimmering waters of Cuyahoga River, the perfect way to begin your Cleveland stay.
Today, set out to explore some of the Cleveland's top attractions, starting with an included visit to the Rock & Roll Hall of Fame — an absolute must for music lovers. Dive into decades of rock history as you browse fascinating exhibits featuring legendary artists, iconic instruments, and immersive multimedia experiences. Afterwards, wander along the Lake Erie waterfront, where the striking architecture of the Great Lakes Science Center and the Huntington Bank Field, home of the Cleveland Browns, create a dynamic skyline.
Spend the afternoon in University Circle, Cleveland’s renowned cultural district, where you’ll find the Cleveland Museum of Art, one of the finest in the U.S. with a vast collection spanning 6,000 years, and the Cleveland Botanical Garden, a serene escape filled with lush greenery. As evening falls, return to Downtown Cleveland to enjoy dinner in the lively East 4th Street Entertainment District, where buzzing restaurants and live music set the perfect tone for a night out in the city.
Enjoy a leisurely breakfast before spending your final day discovering more of Cleveland’s attractions at your own pace. If you’re in the mood for nature, head to Cuyahoga Valley National Park, just a short drive from the city, where scenic trails, waterfalls, and the Cuyahoga Valley Scenic Railroad await. Alternatively, stay local and explore the Cleveland Metroparks, known as the city’s “Emerald Necklace” — a network of beautiful green spaces perfect for walking, cycling, or simply relaxing outdoors.
Back in the city, explore West Side Market, Cleveland’s oldest public market, where you can browse local produce, international treats, and freshly baked goods before lunch in the trendy Ohio City neighbourhood. For art and culture lovers, consider a visit to the Museum of Contemporary Art Cleveland (MOCA) or browse the independent galleries and boutiques scattered throughout the Tremont or Detroit Shoreway neighbourhoods.
Later in the day, transfer independently to Cleveland Hopkins International Airport for your flight home.