From Blues to Rock to Broadway

Arrive in the Windy City and make your way to your centrally located hotel. After settling in, enjoy a leisurely evening stroll along the Chicago Riverwalk — a perfect introduction to the towering skyline and vibrant city energy. Choose from a variety of waterfront restaurants for dinner before resting up for a full day of exploration ahead.

Today, make full use of your included Chicago CityPASS®, giving you access to some of the city’s most famous attractions. Head up to Skydeck Chicago at Willis Tower or 360 CHICAGO for breathtaking panoramic views over Lake Michigan and the skyline. Spend the afternoon exploring Millennium Park and snap a photo beside the iconic Cloud Gate sculpture. If time allows, visit the world-renowned Art Institute of Chicago or explore the spectacular Museum Campus along the lakefront. In the evening, dive into Chicago’s incredible dining and nightlife — perhaps even enjoy some deep-dish pizza, a city staple.

Use your additional day in Chicago to continue exploring with your CityPASS®. An architectural river cruise offers a relaxing and insightful way to appreciate Chicago’s world-famous architecture. Wander Navy Pier for shopping, dining, and lake views, or spend time in Lincoln Park, home to beaches, gardens, and the popular Lincoln Park Zoo. Tonight, enjoy a theatre show or a blues club for an authentic Chicago nightlife experience.

Spend your final day in Chicago at leisure — perhaps shopping along the Magnificent Mile or exploring more neighbourhood gems. This evening, board your overnight Amtrak train bound for Cleveland. Relax in comfort as you glide through America’s Midwest under the stars.

Arrive in Cleveland early this morning and head straight to your hotel, where immediate room access is waiting for you. Take the day at a gentle pace, exploring the lakefront district and vibrant downtown area. Enjoy a relaxed dinner in the buzzing East 4th Street entertainment district before settling in for the night.

This morning, walk to one of Cleveland’s most celebrated attractions — the Rock & Roll Hall of Fame. Your included admission brings you face to face with the music legends who changed the world, with interactive exhibits, rare artefacts, and a look into the evolution of rock culture. After an exhilarating visit, continue discovering Cleveland’s urban heart in The Flats or perhaps join a Guardians baseball game (seasonal). Evening options include breweries, riverside dining, and live music venues that celebrate Cleveland’s creative spirit.

Spend your final day in Cleveland exploring more of its cultural and scenic highlights. Head to University Circle — one of the most impressive arts and cultural districts in the U.S. — where you can visit the world-class Cleveland Museum of Art, wander through the lush Cleveland Botanical Garden, or explore the fascinating Cleveland Museum of Natural History. For a more relaxing afternoon, venture to Edgewater Park to enjoy Lake Erie views, walking trails, and perhaps a lakeside picnic. As evening arrives, experience Cleveland’s friendly nightlife in neighbourhoods like Ohio City or Tremont, where independent restaurants, breweries, and live-music venues showcase the city’s creative spirit.

After breakfast, board the early Amtrak departure for New York City. Enjoy a scenic ride across Pennsylvania and New Jersey, arriving in the city that never sleeps by early evening. Check into your hotel before heading out to see Times Square come alive under the bright lights of Broadway.

Your New York CityPASS® provides access to several of the world’s most iconic attractions. Take a ferry to Liberty Island to see the Statue of Liberty up close, then visit Ellis Island for a powerful look at America’s immigrant history. Spend the afternoon taking in breathtaking skyline views from the Empire State Building or Top of the Rock. As night falls, stroll through Central Park or catch a Broadway show — the perfect New York evening.

Continue exploring with your CityPASS® — whether that means admiring masterpieces at The Metropolitan Museum of Art, standing beneath the space shuttle at the Intrepid Sea, Air & Space Museum, or embarking on an architectural harbour cruise. Wander SoHo’s shops, visit Grand Central Terminal, or enjoy the vibrant atmosphere of Greenwich Village as you craft your perfect final full day in New York.

Make the most of your final hours in New York — enjoy a last stroll through Central Park, visit a rooftop viewpoint, or indulge in a final local treat like a New York bagel or slice of cheesecake. When the time comes, transfer independently to the airport for your flight home.

Want more time to explore the East Coast?
You can continue your adventure effortlessly by rail: Extend your journey to Boston, Philadelphia, or Washington, D.C. — all iconic cities only a few hours away.