Big Apple to Chicago

United States Of America,

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13 people
8 days
Code: SSVD
Activity and Adventure, Discovery, Tours
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Overview of Big Apple to Chicago

See all that The United States’ east coast has to over on an adventure through the nation’s sprawling metropolises and unspoiled nature reserves. Starting in New York and finishing in Chicago, discover the immaculately manicured gardens of Washington DC, the rolling peaks of the Appalachians and Great Smoky Mountains, the southern comfort of Kentucky and the country twang of Nashville. Get lost in the glitz of Dollywood or seek out an authentic blues experience in the streets of Chicago. The eclectic eastern US has something for everybody.

Trip Summary for Big Apple to Chicago

Start Location: Newark,   End Location: Chicago

Countries Visited: United States Of America,
Meals Included: Breakfast: 0   Lunches: 0   Dinners: 0

    • Chicago’s lakefront footpaths are nearly 45 kilometres in length and run beside the stunning Lake Michigan. Free time here means you can either walk the trail or take a boat across the waters
    • For unforgettable scenes of rural America, take in the views along the 105 mile Skyline Drive in Shenandoah National Park
    • Washington DC was built with the blocks of American history and is great to explore by day and night. See the monuments and memorials of the capital on an optional bike tour
    • The flexibility of this trip allows you to do what you want, when you want and without the restrictions of a packed itinerary


Day 1 - New York (Newark)
Welcome to the USA. You can arrive at any time as there are no activities planned until your welcome meeting in the hotel lobby at 6pm. If you're going to be late, please inform the hotel reception. We'll be collecting your insurance details, food kitty and next of kin information at this meeting, so please ensure you have all of these details to provide to your leader. If you arrive early, perhaps see the sights of Manhattan, such as Times Square, Broadway or Central Park. As there's no time spent in New York City on this trip, we recommend you arrive a few days earlier to see the sights. Consider joining our one-day sightseeing tour of New York at

Day 2 - Philadelphia/Washington DC
Leave New York behind in the morning and journey to Washington DC, stopping to visit Philadelphia along the way. Founded in 1682, Philadelphia is home to the Liberty Bell and it was here that Thomas Jefferson signed the Declaration of Independence in 1776. You'll have time to see a couple of the highlights of this city before continuing on to Washington DC. Don't worry about not having too much time to explore today, as you'll have a full free day tomorrow.

Day 3 - Washington DC
Today is a free day to explore Washington DC, with the city being easily explored on foot. To see as much as you can today, it may be an idea to get a map and make a plan. Don't miss the White House, Capitol Building, Washington Monument, Lincoln Memorial, and National Air and Space Museum. These are just a few of the optional activities available, as there as tons of museums, monuments and parks to venture to.

Day 4 - Blue Ridge Mountains
This morning you'll cross into the state of Virginia and drive along the scenic Skyline Drive in Shenandoah National Park, to the Blue Ridge Mountains in the south of the state (approximately 8 hours). The Blue Ridge Mountains are one of the most beautiful and iconic parts of the American landscape, with an abundance of flora and fauna peppering the steep slopes of the mountains. This is a long travel day but it is incredibly scenic with views over the Shenandoah Valley along the way, as well as the snaking and looping Shenandoah River.

Day 5 - Great Smoky Mountains
Cross into the state of Tennessee this morning to the town of Gatlinburg in the Great Smoky Mountains (approximately 2-3 hours). Depending on the group's arrival time, you should be able to use your free time to see some of the town's attractions. Take a stroll on one of the nearby trails or pay a visit to Dollywood, the Dolly Parton-themed amusement park that's also owned by the singer.

Day 6 - Nashville
Drive approximately 4 hours east to Nashville, Tennessee. Once settled into the campground, perhaps visit the Country Music Hall of Fame, which contains the golden Cadillac that once belonged to Elvis. Another point of interest is Music Row, where more than 50 recording studios and approximately 200 music publishing houses are located. The Wildhorse Saloon is a great spot in the evening to experience authentic southern food and live music.

Day 7 - Louisville
Leave Nashville behind today and drive north for around three hours to Louisville, Kentucky. On arrival, you'll have free time to explore this huge city. Louisville is perhaps best known as being the home of the Kentucky Derby, although it's also famous in baseball circles as being the birthplace of the Louisville Slugger bats. Aside from sports, Louisville has an up-and-coming food scene, several interesting museums, pretty parks, the largest collection of Victorian-era homes in the country, and to top all that, it is the final resting place of Colonel Sanders. Of course Kentucky is also well-known for its bourbon, and in Louisville you can follow the Bourbon Trail, learn about the history of the beverage, visit distilleries and perhaps trying a sample or two.

Day 8 - Chicago
Enjoy a six hour roadtrip to Chicago, where this American adventure comes to an end on arrival. There are plenty of things to see and do during your extra time here. With more than 45 kilometres of lake front paths, Chicago is also one of the world's most walkable cities so it's a great place to explore on foot. For amazing views of Chicago, visit the Skydeck at Willis Tower, which has huge glass panels and a glass balcony so you can see all the way down. In the evening, search out an authentic blues bar for a night of music. B.L.U.E.S is a great place to spend your evening, but be prepared to be drowned out by the music. Please note no accommodation is provided tonight.

The arrival time depends on each group, but if you decide to fly out on this day, please don't book a flight before 9pm. This will give you enough time to catch a shuttle from the hotel to the airport and be there two hours before departure. As there's a great deal to do in Chicago, staying a few extra days to make the most of this exciting city is recommended. If you need help booking extra accommodation (subject to availability), our reservations team will be happy to assist you.

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