USA & Canada Adventure
Departure dates & prices
Day 1 - New York City, New York to Boston, Massachusetts
This is it. The moment you’ve been dreaming about. The start of your big adventure. And where else would you start, but the Big Apple? Meet the gang, stock up on snacks and whip out the AUX cord – we’re heading to Boston first-thing. 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? Get cheers-ing with your trip mates over tonight’s included dinner. This is gonna be good.
Day 2 - Boston
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. Or head to Faneuil Hall Marketplace for alllll the foodie goodness. Then, hunt down the perfect cannoli in North End. It doesn’t get much better than this.
Day 3 - Boston to Quebec City, Quebec
Wave goodbye to Beantown – the French-speaking city of Quebec is calling our name. Oh là là. Fun fact: Quebec City is one of North America’s oldest settlements. True story. We’ve got a bit of a drive across the Canadian border, so settle into the fact-filled spiel your Trip Leader’s got planned or verse your trip mates to a not-so-friendly game of UNO. 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 4 - Quebec City to Montreal
Au revoir, Quebec – we’re swapping you 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 5 - 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 6 - Montreal to Toronto, Ontario
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 pat. When we reach T-dot, tick off all the showstoppers on a walking tour. We’re talking: 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 7 - Toronto
A city exploding with culture and seriously good food – 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 8 - Toronto to Detroit, Michigan via Niagara Falls
Down that coffee and wave goodbye to Toronto – we’re outta here after breakfast. But before crossing back into the States, 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). Then: we’ll roll onto Detroit – where a driving tour of the city’s A-listers awaits. 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 9 - 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 10 - Detroit to Chicago, Illionois
Nobody panic – but the adventure is winding up. Our final destination? Chicago. Spend the ride catching up on some zzz’s and swapping those socials with your trip mates. We’ll kick 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 tonight: Chicago’s famed deep-dish pizza. You know you wanna try it.
Day 11 - 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 give this adventure the send-off it deserves – the sweet sounds of Uptown’s jazz bars are calling...
Day 12 - Chicago
And just like that, it’s all over. Get down to breakfast and say your goodbyes (no tears, pls). You’ve still got time to plan next year’s reunion trip. Where to next?
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