Itinerary
- Day 1
Arrival in Chicago
You'll land in Chicago and head to your accommodation using public transit or a cab. The city's tall buildings create those famous canyons between streets, and once you're settled, there's time to walk around and get a feel for the place. That strong Chicago wind? You'll notice it right away, especially down by the lakefront.
Optional Activities
- Explore Chicago's skyscraper canyons on foot
- Day 2
Chicago Landmarks
Grant Park and Buckingham Fountain are the main stops today, with that distinctive curved metal sculpture at Millennium Park being worth the walk through downtown. From there, you can either take a boat tour along the Chicago River to see the city from the water, or head up to the Hancock Tower for views over the city at sunset. Your choice depends on how much walking you've done already.
Included Activities
- Visit Grant Park and Buckingham Fountain
- View Cloud Gate sculpture at Millennium Park
Optional Activities
- Chicago River excursion boat tour (payable locally)
- Hancock Tower visit for city views, especially at night (payable locally)
Landmarks Buckingham Fountain Cloud Gate Hancock Tower Chicago River 
- Day 3
Chicago Neighborhoods
Start this morning in Wicker Park, where the streets have colorful murals and the cafes are packed with locals. The 606 greenway runs right through this area and it's perfect for a relaxing walk if you need a break from the downtown crowds. Later, head to the West Loop and walk through Randolph Street and Fulton Market where restaurants and bars line the streets, especially after work hours when the neighborhood really comes alive.
Optional Activities
- Explore Wicker Park neighborhood
- Walk or relax on The 606 elevated greenway
- Explore Randolph Street and Fulton Market in West Loop
Landmarks Wicker Park The 606 Logan Square Humboldt Park - Day 4
Chicago to New York
After your flight lands in New York, get checked in at the hotel and then head right back out into the city's pace. The Edge gives you incredible views of all five boroughs from way up high, and then Times Square hits you with the crowds and energy of the city all at once. It's loud and chaotic and that's kind of the point.
Included Activities
- Visit Times Square
Optional Activities
- The Edge observation deck visit for skyline views (costs extra)
Landmarks Times Square The Edge 
- Day 5
New York City
Set your alarm for sunrise and head to the Brooklyn Bridge early when there aren't too many people around yet. The light on Manhattan from the bridge is different than anywhere else in the city. Grab a bagel for breakfast, then catch the free Staten Island Ferry which gives you views of the Statue of Liberty from the water. The 9/11 Memorial downtown is quiet and reflective, and then you can spend the afternoon wandering through Greenwich Village with its tree-lined streets and small shops.
Included Activities
- Brooklyn Bridge at sunrise
- Staten Island Ferry ride (free)
- 9/11 Memorial visit
- Explore Greenwich Village
Optional Activities
- Breakfast at Ess-a-Bagel
Landmarks Brooklyn Bridge Staten Island Ferry Statue of Liberty 9/11 Memorial Greenwich Village 
- Day 6
New York City
Ellen's Stardust Diner has those singing waiters performing while you eat breakfast, which is pretty entertaining even if you're not a Broadway fan. Walk through the theater district to look for last-minute ticket deals if there's a show you want to catch. Spend the afternoon in Central Park with a coffee, watching people and just sitting. By evening, head to Midtown and grab food from the street vendors, trying hot dogs or whatever looks good from the food trucks around the skyscrapers.
Included Activities
- Visit Central Park
- Explore Midtown Manhattan
Optional Activities
- Breakfast at Ellen's Stardust Diner (singing waiters)
- Broadway musical tickets (last-minute deals available)
Landmarks Ellen's Stardust Diner Central Park Empire State Building Flatiron Building - Day 7
New York to Washington D.C.
Take a morning walk on the High Line, which is an old elevated train track turned into a park with art installations and gardens. After that, head to the Amtrak station for your trip down to Washington D.C. The train ride is scenic, especially through New Jersey and Pennsylvania. Once you arrive and check in, explore Georgetown with its historic townhouses and the small cafes tucked along the streets and alleys.
Included Activities
- High Line walk
- Amtrak train journey to Washington D.C. (Coach Class with seat reservation)
Optional Activities
- Explore Georgetown neighborhood
- Meal at Ben's Chili Bowl (optional, payable on site)
Landmarks High Line Georgetown Ben's Chili Bowl 
- Day 8
Washington D.C.
The Capitol offers free tours if you want to go inside, or you can walk around the building and explore the National Mall on foot. The Lincoln Memorial is at one end and the Washington Monument at the other, with free museums all along the way including the Natural History Museum and Museum of American History. You can spend an entire day here without paying anything. Grab a spot on the lawn to rest and check out the White House from the north side.
Included Activities
- Capitol building tour (free)
- Visit Lincoln Memorial
- Visit Washington Monument
- Natural History Museum (free)
- Museum of American History (free)
- View White House
Landmarks Capitol Lincoln Memorial Washington Monument National Museum of Natural History National Museum of American History White House National Mall 
- Day 9
Washington D.C. to Miami
Fly from D.C. to Miami where the weather shifts immediately warmer. Get to South Beach and walk along Ocean Drive, which has palm trees on both sides and older Art Deco style buildings painted in pastels. The beach itself is right there, so you can see both the architecture and the ocean. Have dinner at Naked Taco or somewhere similar to mark your first night in Miami with good food and a sense of arrival.
Included Activities
- Visit South Beach
- Walk Ocean Drive
Optional Activities
- Dinner at Naked Taco
Landmarks South Beach Ocean Drive 
- Day 10
Miami
Start early at Versailles Restaurant in Little Havana for Cuban breakfast, which means strong coffee and a Cubano sandwich that's different from what you'll find in other cities. Walk through Calle Ocho where you'll hear salsa music and see Cuban flags and cultural shops. Then head back to downtown Miami and see the modern skyline, before going to Wynwood where graffiti covers the walls as art. The area has galleries, breweries, and shops mixed between the colorful murals.
Included Activities
- Explore Little Havana
- Walk Calle Ocho
- Explore Wynwood neighborhood
Optional Activities
- Breakfast at Versailles Restaurant (at your own expense)
Landmarks Little Havana Calle Ocho Wynwood 
- Day 11
Departure from Miami
This is your last few hours before heading to the airport. If there's anything you missed or wanted to do again, this is the time. Otherwise, spend it relaxing at your hotel or finding a cafe to sit and think about everything you've seen across the different cities.
Optional Activities
- Tick off remaining bucket list items
- Day 12
Arrival Home
You land back home and the trip is done. All those stories about Chicago, New York, D.C., and Miami are now yours to tell, and the memories from seeing all these different parts of the country will stick with you.
