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Capone's Trail 2017 (7 Days, New York to Chicago)

Travel 'like a boss’ on this rollicking ramble from New York to Chi-town, taking in the best of Washington D.C., Philly and Cleveland en route. Take a bite out of The Big Apple, explore the nation’s capital, jam out in the 'Rock 'n’ Roll Capital of the World’ (Cleveland) and channel your inner mobster in the Windy City. You’ll get your fix of the urban, a generous slice of history and even a look into Amish life, all while making memories to last a lifetime.


Washington DC night time illumination tour
360 Chicago Observatory
Rock N Roll Hall of Fame
5 Breakfasts
5 Dinners
Tour Provider Topdeck
Number of Days
Price From
AUD $1,785
Start Location
New York, United States
End Location
New York, United States
Age Range
Avg. 39+
Group Size
1 to 48
Tour Style
Tour Themes
Physical Rating
Day 1: New York City to Washington, District of Columbia, via Philadelphia, Pennsylvania
Leave the bright lights of the Big Apple behind for DC, via Philly. Take a driving tour of Philadelphia to see the sights - you'll channel your inner champ at the Rocky statue, and feel the love as you swing by the Love statue. For a bird's eye view of the city, you can choose to head to the One Liberty Observation Deck. Enjoy an illuminated tour of the capital's monuments when you hit Washington tonight. Included today: -Driving tour of Philadelphia -Illumination tour in DC Meals: -Dinner
Day 2: Washington, DC
Snap yourself in front of some of the US's most iconic buildings, recreate famous movie moments or spot a senator - today you can get a real feel for the powerhouse that is DC. Get your bearings and tick off all the must-see places with an optional hop on/off bus tour. Most of the museums are free, so get hopping and make the most of them. Meals: -Breakfast Optional activities: -Segway tours -Bike tours
Day 3: Washington, DC
Day two of doing your own thing. Speed your way past the likes of The White House and Washington Monument by seeing the city on a segway tour, or go for pedal-power with a leisurely bike tour. This is the place to clue yourself up on all things American history and visit some of the many memorials, monuments and museums. Meals: -Breakfast Optional activities: -Segway tours -Bike tours
Day 4: Washington, DC to Cleveland, Ohio
Swap the capital for Cleveland, otherwise known as the 'Rock 'n' Roll Capital of the World'. When you arrive, challenge your music knowledge and see some of the greats with a tour of the Rock 'n' Roll Hall of Fame. Work your way through Blues and Bluegrass, Gospel and R 'n' B and (of course) Rock 'n' Roll, and come out a music aficionado. Included today: -Rock 'n' Roll Hall of Fame Meals: -Breakfast
Day 5: Cleveland to Chicago, Illinois, via Amish Country, Indiana
Shipshewana. Indiana. On your way to The Windy City, stop in Amish Country and see life lived at a slower pace. Then it's time to switch things up and hit Chicago. See the city from up high at the 360 Chicago Tower Observatory, and then charge yourself up so you're ready to take on the city for tomorrow's free day. Thrills, spills and lashings of good food await. Included today: -360 Chicago Tower Observatory (incl. TILT) Meals: -Dinner
Day 6: Chicago
If you're feeling brave, take the jet boat out to experience the Great Lakes at 35 MPH, or if spectator sports are more your thing, try the Wrigley Field tour. Go Cubs go! Whatever you do, make sure you get well acquainted with the city's famous deep dish pizza and other Chicagn treats like jibarito sandwiches and Chicago dogs. Just remember the cardinal rules - poppy seed bun and no ketchup - it's the way the locals do it. Meals: -Breakfast Optional activities: -Jet boat -Wrigley Field Tour -Food tour
Day 7: Chicago
This morning it'll be time to say goodbye to your travel buddies, this trip is coming to an end. But why not stick around? If you haven't tried Chicago Popcorn, you've got to track it down. Yes it's caramel and cheddar cheese flavour, but that crazy combo is dangerously moreish. Trust us. Meals: -Breakfast