Great Cities of the Great Lakes

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 two full days to explore Chicago, your included two-day hop-on-hop-off sightseeing tour offers the perfect way to discover the Windy City at your own pace. This flexible pass allows you to hop between Chicago’s most iconic landmarks, world-class museums, and vibrant neighbourhoods while enjoying expert commentary and panoramic city views along the way.

Start your adventure with breathtaking skyline vistas from the Skydeck at Willis Tower or 360 CHICAGO Observation Deck, then wander through Millennium Park to see the famous “Cloud Gate” sculpture — affectionately known as The Bean. Stroll the nearby lakefront, explore Navy Pier’s attractions, or stop for a classic Chicago-style hot dog along the way.

On your second day, dive deeper into Chicago’s cultural scene with a visit to the Art Institute of Chicago, home to one of the world’s best collections of Impressionist and American art. Discover the Magnificent Mile’s mix of designer boutiques and local eateries, or take an architectural river cruise for a unique perspective of the city’s celebrated skyline. As evening falls, relax along the scenic Riverwalk or enjoy a memorable dinner in one of Chicago’s renowned restaurants — perhaps sampling deep-dish pizza or catching live jazz in a downtown club.

This morning, collect your rental car and travel north into Wisconsin and visit 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 designed by Santiago Calatrava. The modernist building is shaped like a floating cross, with wings opening and closing from a central base. Even people who’ve never been on a motorcycle will enjoy the Harley-Davidson Museum. Exhibits tell the stories of the extraordinary people, products, history and culture of Harley-Davidson and of-course the fantastic motorcycle collection will captivate all. Continue north to Green Bay for the next two nights.

Twice awarded the title of All-America City, Green Bay is known as “Titletown” because of the number of professional football Super Bowl titles its team, the Green Bay Packers has won. It’s also a great starting point to visit Door County, 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 day hunting for treasures in one-of-a-kind shops, galleries, museums & lighthouses. Pick a pail of ripe Door County cherries in the summer or a basket of crunchy apples in fall. Return to your hotel in Green Bay for the overnight.

Continue north to Marquette, the largest city on the Upper Peninsula of Michigan and the home of Northern Michigan University. It is a major port on Lake Superior, the largest of the Great Lakes. Take time for relaxing on the beach or enjoying some recreational hikes. The warm weather months offer many festivals including Art On The Rocks art festival and the Hiawatha music festival.

Nestled on the shores of Lake Superior, Marquette is a hidden gem that perfectly captures the spirit of Michigan’s Upper Peninsula — where natural beauty, outdoor adventure, and small-town charm come together. With one full day to explore, start your morning with a stroll along the scenic Lake Superior shoreline at Presque Isle Park, a 323-acre peninsula offering walking trails, dramatic cliff views, and the chance to spot local wildlife. For a more active start, hike to the top of Sugarloaf Mountain for panoramic views of the city, lake, and surrounding forest — especially breathtaking in autumn.

Afterwards, wander through Marquette’s historic downtown, where restored 19th-century buildings house independent shops, art galleries, and cafés. Stop for lunch at a local brewery or lakeside restaurant to enjoy fresh-caught whitefish — a regional favourite. In the afternoon, visit the Marquette Maritime Museum and Lighthouse, where you can learn about Lake Superior’s fascinating shipping history and the region’s maritime heritage.

As the day winds down, take a sunset walk or drive along the Black Rocks, a striking natural formation popular with cliff divers and photographers alike. For dinner, enjoy a relaxed evening at one of Marquette’s inviting farm-to-table restaurants or craft breweries, sampling local beer made with the region’s pure Lake Superior water.

Travel south to Mackinac Island. Board the ferry in St Ignace for the 20 minute hi-speed ferry to the island where Victorian sensibility predominates. Bicycles and horse-drawn carriages are the modes of transportation on this island in the straits of Mackinac where the upper peninsula of Michigan meets the lower peninsula. Take a self guided hiking tour or rent a bicycle to tour sites such as arch rock, skull cave, sugarloaf, British landing, devil's kitchen and the beach of a bazillion beautiful skipping stones, or just take a carriage tour and eat the fudge the island is famous for. Return to the mainland and travel to Traverse City for the next two nights.

Set out for Sleeping Bear Dunes National Lakeshore this morning - a must see. It offers magnificent views over sweeping vistas of Lake Michigan from atop high dunes, miles of perfect freshwater beaches, forested wilderness islands, hiking trails and a series of preserved historic farmsteads. In the afternoon visit some of the local wineries. Located on the 45th parallel, Traverse City is home to vintners who grow grapes and bottle wines on the scenic Old Mission and Leelanau Peninsulas. Overnight in Traverse City.

Known as Motor City because of its’ notoriety as the world's traditional automotive center, and as Motown for its importance as a source of popular music legacies, the city offers a host of activities to the traveler that lends itself to both cultures. Spend the next two nights in Detroit.

Spend the day visiting Detroit’s highlights such as the Henry Ford Museum and Greenfield Village, and the Motown Museum, better known as “Hitsville USA”. Here one can stand in Studio “A” where the likes of Stevie Wonder, the Temptations, the Four Tops, Gladys Knight and the Pips, Diana Ross and the Supremes, and the Jackson Five, among others, recorded their hits. Overnight in Detroit.

Today’s journey takes you from the energy of Detroit to the vibrant lakeside city of Cleveland — a scenic drive of just under three hours that offers plenty of opportunities to pause and enjoy the Great Lakes region along the way.

As you continue towards Cleveland, the route becomes more relaxed, offering glimpses of peaceful countryside and Lake Erie’s distant shoreline. Upon arrival in Cleveland, return your rental vehicle and check into your downtown hotel. The rest of the day is at leisure — perhaps enjoy a gentle evening stroll along the Cleveland Lakefront or through Public Square and treat yourself to dinner in the lively East 4th Street entertainment district. It’s the perfect way to unwind after your journey and begin your Cleveland stay on a relaxed note.

Begin your Cleveland adventure in the city’s cultural heart. Visit the Rock & Roll Hall of Fame, one of America’s most iconic museums, where the stories and sounds of musical legends come to life through interactive exhibits and rare memorabilia. After lunch, explore the nearby Great Lakes Science Center or take a lakeside walk along Voinovich Bicentennial Park for panoramic views of Lake Erie. In the evening, experience Cleveland’s thriving food scene with dinner in the Warehouse District or East 4th Street, both lively areas filled with restaurants, bars, and live entertainment. Alternatively, enjoy a pre-theatre meal before watching a show at Playhouse Square — the largest performing arts centre in the U.S. outside of New York City — and soak up the vibrant atmosphere of this historic theatre district.

Today, discover Cleveland’s rich cultural side in University Circle, home to the world-renowned Cleveland Museum of Art, the Museum of Contemporary Art (MOCA), and the serene Cleveland Botanical Garden. This compact area offers a perfect mix of world-class art, green spaces, and café culture. In the afternoon, venture to Ohio City, a neighbourhood known for its vintage shops and craft breweries. Be sure to visit the West Side Market, Cleveland’s historic food hall, where local flavours and global influences meet. Depending on the season, end your day at a sporting event – whether it’s the Cleveland Guardians (baseball), Cavaliers (basketball), or Browns (American football) – for an authentic slice of local life.

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, browse the independent galleries and boutiques scattered throughout Tremont and Ohio City, each offering a taste of Cleveland’s creative spirit. For museum lovers, return to University Circle to explore more of its cultural treasures, such as the Cleveland Museum of Natural History and the Cleveland History Center, where the region’s fascinating past comes to life.

Later in the day, transfer independently to Cleveland Hopkins International Airport for your flight home.