USA & Canada Adventure (ex. Chicago) 2021

From Chicago to New York

Visiting: USA, Canada

Tour Operator: Topdeck

Prices From:

Tour Overview

Is this trip for you? HISTORIC. DIVERSE. LIVELY.   Game time: would you rather travel the USA or Canada? Psych! On this 12-day adventure you get both rolled into one. Thank us later. From the land of the free and beyond, we'll tick of the A-listers Boston, Quebec City, Montreal, Toronto, Detroit and Chicago. Plus, get sprayed (in the best way) by the mighty Niagara Falls. Visit the homes of sporting legends. Test our waistbands with alllll the diverse foodie delights. And uncover the culturally rich neighbourhoods at the heart-and-soul of these incredible cities. You ready to embrace it all? We thought so.

Places You'll See



Map Image
Day 1: Chicago, Illionois

This is it. The moment you’ve been dreaming about. The start of your big North American adventure. Meet the gang at the hostel – we’re kicking things off in Chi-Town with a driving tour around the Magnificent Mile, John Hancock Building, Navy Pier and Millennium Park. And on the menu for tonight’s included dinner: Chicago’s famed deep-dish pizza. You know you wanna try it.

Day 2: Chicago

Today, you’ve got a full free day to spend exploring the Windy City. Need some suggestions? We’re glad you asked. Hire yourself a set of wheels and delve deeper into the city’s countless culturally rich neighbourhoods. Get float-y and take in the city’s famous landmarks on an architecture boat cruise. Or opt for the bird’s eye view on a heli-tour. If you picked the right season, you might even be able to catch a Cubs game at Wrigley Field. Snap THAT pic at ‘The Bean’. Wander along the riverfront. Gape at the masterpieces in Chicago’s Institute of Art. Then: get the gang together and head to one of Uptown’s jazz bars.

Day 3: Chicago to Detroit, Michigan

Today, we roll onto Detroit – where a driving tour of the city’s A-listers awaits. Tick off the likes of Fox Theatre, Ford Field, Campus Martius, the Guardian Building and the infamous American vs Lafayette Coney Island hotdog stores. You gotta try them both, obvs. After an included dinner with the gang, it’s time to see why they call this place Rock City (hint: it’s got nothing to do with the landscape).

Day 4: Detroit

You wanted more free time to explore – so here’s 24hrs we prepared earlier. Don’t waste a second. Head to the Henry Ford Museum to uncover over 300 years of American innovation. Find out “What’s Going On” with a trip to the Motown Museum. Soak up the city’s incredible art scene with a visit to Detroit Institute of Arts. Gape at the Guardian Building (aka Detroit’s Cathedral of Finance). Sip your way around the hipster craft brewery scene. Then: head to Greektown for all your foodie desires (with a few hip bars thrown in for good measure).

Day 5: Detroit to Toronto, Ontario via Niagara Falls

Down that coffee and wave goodbye to Detroit - we're outta here after breakfast. But before crossing back into Canada, we'll treat our eyeballs to the 'holy sh*t'-worthy Niagara Falls. Watch from Table Rock as 600,000 gallons of water cascade into a thunderous show of mist and rushing water. Wanna get closer? There's an optional boat tour on the cards (if you brought your raincoat). When we reach T-dot, tick off all the showstoppers on a walking tour - we're talking the CN Tower, Rogers Centre, Old City Hall, Yonge-Dundas Square and Hockey Hall of Fame. Then, get stuck into an included dinner with the gang before we sample a slice of this city's famous nightlife.

Day 6: Toronto

Sum up Toronto in one word: diverse. Welcoming over 40 million people annually to the city that speaks over 140 different languages and is home to Canada’s largest LGBTIQ+ community – this place has got acceptance down to a tee. And you’ve got 24hrs of freedom to embrace it all. So, don’t muck about. Do the obvious and scale the CN Tower – with a stomach-churning glass viewing platform at over 342m high, this one’s pretty epic. Let your inner hockey-freak flag fly at the Ice Hockey Hall of Fame (home to the Stanley Cup). Wander the cobbled alleyways of the Distillery District. Put your waistbands to the test at St Lawrence Market. Explore the ninety-eight OTT rooms of Casa Loma. Channel your inner hipster at Kensington Market. Then, head to Chinatown for cheap beers and drool-worthy dumplings. This is what you came for.

Day 7: Toronto to Montreal, Quebec

We’re swapping Toronto for Montreal today. Sorry, not sorry. Dump your stuff and get exploring – this place packs some serious colonial history. Head to Old Montreal and check out the Place d’Armes, Place Royal and Notre Dame Basilica. Get all the views of City Hall and Nelson’s Column from Place Jacques-Cartier. Stroll along the waterfront and Old Port. Then: flash some plastic amongst the boutiques and stalls in Bonsecours Market. Just be back in time for tonight’s included dinner with the gang.

Day 8: Montreal

Today, it’s all about you. Need some suggestions? Put your fat pants to the test on a food tour of the Mile End district. Think: three hours of the best carb-laden, cheese-topped, bagel-shaped stops in the city. Mmmmm. Or tackle the Lachine Rapids with an adrenaline-fuelled jet boating experience. Spoiler: you will get wet. Prefer to do your own spontaneous this-is-what-I-came-here-for thing? Climb Mt Royal for alllll the views. Get your history-fix at the Montreal Museum of Archaeology and History. Or uncover the maze of shops and museums hidden beneath the city streets at the Underground City. Tonight, you’re in Disneyland for foodies – go get it.

Day 9: Montreal to Quebec City

Spend the morning ticking off the last Montreal must-eats on your list, before we roll out this afternoon. Quebec is calling our name. Oh là là. Fun fact: Quebec City is one of North America’s oldest settlements. True story. After tonight’s included dinner, we’ll have the option to wander the cobblestone streets on a spine-tingling ghost tour. With over 400 years of murder, tragedy and hauntings – you might need a spare pair of undies for this one.

Day 10: Quebec City to Boston, Massachusetts

Au revoir, Quebec – time to head back to the States. Disclaimer: we’ve got a bit of a drive across the border so, catch up on some zzz’s or verse your trip mates to a not-so-friendly game of UNO. A city that was key to the American Revolution and Independence movement, Boston has got a history – and our expert Trip Leader has the low-down on today’s walking-driving tour. Tick off the likes of Bunker Hill, Charleston Bridge, the USS Constitution and North End Neighbourhood. Then? Head to Faneuil Hall Marketplace for alllll the foodie goodness or hunt down the perfect cannoli in North End. It doesn’t get much better than this.

Day 11: Boston

Right, this is your day – your way. But if you need some suggestions, we’ve got a couple of the best optional activities lined up. Get on your bike and explore six different neighbourhoods with an in-the-know-local (countless historical facts included). Or brush up on your Red Sox trivia with a visit to Fenway Park. Rather do your own spontaneous thing? No worries. Follow the story of the American Revolution along the Freedom Trail. Jump aboard the USS Constitution. Check out the Boston Tea Party Museum. Whatever you do, just be back in time for tonight’s dinner with the gang – we’re gonna give this incredible adventure the send-off it deserves!

Day 12: Boston to New York City, New York

And just like that, it’s nearly over. Pile into the coach one last time and swap those socials – you’ll need them for that reunion trip. When we reach NYC – it’s time to say our goodbyes. Who’s sticking around?

What's Included

  • icon

    -2 nights in hotels (twin or double), 9 nights in hostels

  • icon

    11 breakfasts, 0 lunches, 6 dinners

  • Driving tour of Chicago
  • See Niagara Falls
  • Driving tour of Detroit
  • Walking tour of Toronto
  • Walking-driving tour of Boston
  • -2 nights in hotels (twin or double), 9 nights in hostels
  • Modern air-conditioned coach
  • 11 breakfasts, 0 lunches, 6 dinners
Want to read it later?

Download this tour’s PDF brochure and start tour planning offline


Got a question? Check out our Q&As

View Q&As Ask A Question

Dates & Availability

Select departure month
Instant Booking Available

Monday Jul 26, 2021





Instant Booking Available

Monday Aug 30, 2021





Instant Booking Available

Wednesday Sep 22, 2021





Instant Booking Available

Monday, Jul 26, 2021



Instant Booking Available

Monday, Aug 30, 2021



Instant Booking Available

Wednesday, Sep 22, 2021