Becca Challis
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Road trips have become the go-to travel method for many of us to explore domestically dreamy socially distance times.

Follow this itinerary for a 3-week adventure across a country with one of the most stunning landscapes, foodie-friendly spots, and worthwhile tourist spots in the world: Oh, Canada!

Start Your Canadian Road Trip in New York

Day 1

  • Begin your day in Central Park and spend the day finding the best cookies and bagels in the city, such as Levain Bakery, Dominique Ansel, and Absolute Bagels, while exploring the reservoir and other famous park sites.
  • Have dinner at Urbanspace West 52nd, a great street food market with a fun interior, which allows you to choose your preference for dinner!
  • Walk 5th Avenue in the evening to gather your bearings and see sights like the Empire State Building, the Rockefeller Building, and the Flatiron Building.
The cookie cup at Dominique Ansel (every bit as good as it sounds).
Picture of the two of us on Brooklyn Bridge.

Day 2

  • Visit NY Public Library to take in the ceilings of the Rose Reading Room, or head to the Children’s room to see the original toys which inspired A. A. Milne’s Winnie the Pooh.
  • Have lunch at Murray’s and Joe’s Pizza. We went halves on a grilled cheese from Murray’s, which is famous for its cheese pull, and then headed to Joe’s to try their fabled slice.
  • We walked down to Wall St. and continued down to take a stroll across the iconic Brooklyn Bridge. Remember to keep an eye out for fast-moving bikes because it’s always busy!
  • Stroll through Brooklyn around DUMBO and enjoy the views of Manhattan, before heading back on the subway for dinner.
  • Devour your dinner at Barnacho, an awesome Mexican restaurant with a great variety of tacos (including veggie options!) and a fun margarita spin-off, called a Bulldog.
Becca in Downtown New York.
Times Square at night, complete with Statue of Liberty performer.

Day 3

  • Explore Little Italy and ChinaTown.
  • Eat up at Tasty Dumpling for lunch and enjoy their authentic fresh vegetable or pork dumplings at a great price and a non-touristy setting.
  • Next, visit the 9/11 Memorial and St Paul’s Chapel. This landmark is a must for anyone visiting NY to inform you about the tragedy and its impact on New York.
  • Afterward, walk the High Line. This was one of my favorite experiences in NYC because it is a rare glimpse at the city from mid-level. The plants are beautiful too, and I love the independent businesses which set up pop-ups along the walkway.
  • Indulge in your dinner at Black Iron Burger where they sell a solid NY burger and everything is done right.
  • Revel in Times Square at Night and grab some NY cheesecake (it had to be done) from Junior’s and wander around, taking in the bright lights and street performers.

See the Gilmore Girl’s Set Inspo Along Your Drive To Niagara

Day 4

  • Here’s a Top Tip: Pick up a hire car outside of New York City, this way if you’re not super confident driving, New York traffic isn’t the first thing you have to deal with. We took the train from Grand Central Station to Stamford, CT. Here we picked up a car from a hotel car park and got to practice using an automatic for the first time.
  • Drive from Stamford, CT, through the white-churched small towns and, have your Gilmore Girls moment. The main inspirations for the show are New Milford and Washington Depot.
  • Take a route through to Catskill where you can join Route 87 to Albany, before joining Route 90, all the way through to Niagara Falls.
  • Drop off the hire car at Niagara Falls airport and get a taxi to the US side of the Rainbow Bridge border crossing. You can walk across here, saving time and money by not driving through to the Canadian side.
  • Watch the fireworks over the Falls which happen every evening at 10 pm.

Drive from Stamford, CT, through the white-churched small towns and, have your Gilmore Girls moment. The main inspirations for the show are New Milford and Washington Depot. Click To Tweet

The picturesque New Milford – you can almost see Lorelai Gilmore crossing the road.
The sun setting over Niagara Falls.

Check Out The Breath-Taking Niagara Falls

Day 5

  • Explore the beautiful Falls and select which of the Niagara Fall attractions suit you best. Because of time constraints and budget, the Journey Behind the Falls was the best choice for us and we greatly enjoyed it! The viewing platform is fantastic at revealing the power and weight of the water, if not a little damp.
  • Next, take a Greyhound bus to Toronto.
  • We stayed in an Airbnb just off of Bloor St. in downtown Toronto—a trendy and artistic area with colorful street art and a lot of independent businesses (before your stay, remember to ask these important questions and keep these Airbnb safety tips in mind before booking your stay!) I’d highly recommend staying here for a quick walk or subway ride to the center, and a great community feel.
  • Dig into your dinner at COO Cafe Borr. This Japanese-French fusion restaurant on Bloor St has a well-curated menu and delicious, reasonably priced dishes!

Go Sightseeing in Toronto

The red knight at Medieval Times, Toronto.

Day 6

  • Take some time to explore Toronto and get your bearings; visit the bustling CF Toronto Eaton Centre and enjoy browsing in the boutiques. Toronto often has exciting events going on so check before you arrive – we happened to be there on Labor Day weekend, so there were many events to enjoy such as the Harbourfront festival.
  • Sate your appetite after a long day at Medieval Times and watch contestants joust on horseback while handling a chicken wing with your bare hands. Cheer on your knight while you eat, drink, and laugh with your team.

Day 7

  • Walk into Kensington Market from the Westside and definitely stop for breakfast at Boom Breakfast & Co. In Kensington Market, you’ll find the famous garden car alongside stylish eateries and clothing stores. Be sure to visit Moonbean Coffee for a hot drink, especially on a rainy day for the super cozy interior.
  • Visit Graffiti Alley in the historic Fashion District where the art is constantly changing, so even if you’ve been before, it might be worth a second visit.
  • Have fun in the Entertainment District where you can watch the Blue Jays at the Rogers Centre, take in the views from the CN Tower, look at the fish in Ripley’s Aquarium, enjoy a pint or three at the Steam Whistle Biergarten, or play hundreds of arcade games in The Rec Room.
Tim taking a picture of the garden car in Kensington Market.
(Not so) Sunnyside in Toronto with Mississauga visible in the background.

Day 8

  • Rent a bike to pack in as much adventuring as possible. There are hundreds of bike-share stations all over Toronto, so it’s easy to pick up a bike from the nearest station and simply drop it off at your destination.
  • Visit the Distillery District and take a look at the handmade gifts on offer in the market before grabbing some lunch.
  • Savor your lunch at Boku, a great spot if Japanese food is your thing; try the deliciously creamy ramen!
  • To escape the city, take a beautiful cycle along Toronto’s waterfront (feel free to stop if anything catches your eye en route!) to Sunnyside where you’ll find beaches on the shores of Lake Ontario for a chance to relax with ice cream. Bear in mind that the Bike Share stations will empty quickly on a nice day.

There are hundreds of bike-share stations all over Toronto, so it’s easy to pick up a bike from the nearest station and simply drop it off at your destination. Click To Tweet

Take a Break in Calgary

Day 9

  • Take a 4 pm flight from Toronto to Calgary and arrive at 6 pm. Take the bus from the airport to the train station and take the train into the center (Use these search engines to help you find the cheapest flights possible!).
  • Check into your accommodation and grab some takeout to unwind inside. We had Indian food and an early night!

Day 10

  • Explore Calgary, especially 17th Avenue, which is filled with independent restaurants and cafes. The Mall is also a great spot, with an enclosed garden stretching along the top floor, complete with koi carp ponds and fountains.
  • Gobble down some lunch at 5S17, a little Japanese ramen and poke bowl restaurant with outdoor street seating and some killer cocktails.

Cruise Through To Banff, AB and Golden, BC

Day 11

  • This is where we truly start on our Great Canadian Road Trip! Make sure to prepare for the big day with breakfast at Wayne’s Bagels! Stop by this Montreal-style bagel shop to order a custom filled fresh bagel!
  • Next, pick up a hire car and drive towards Banff. Once you’re there, visit Banff (the town), try a Beaver Tail, and hike Tunnel Mountain.
  • Afterward, enjoy the drive to Golden, BC along the Trans-Canada Highway.
  • Check into your accommodation – we stayed at Copper Horse Lodge, on the Kicking Horse Resort. You can grab a hearty dinner from the restaurant in the lodge next door, or their steak house if you visit during the ski season.
A cable car up to the Dogtooth Range.
Boo the Bear, not such a natural climber.

Day 12

  • Purchase a day pass for the Kicking Horse resort and take advantage of everything the Dog Tooth mountains have to offer. Enjoy the ski lifts and gondola to the peak. We visited Boo, the refuge grizzly who has been relocated to the mountainside.
  • Feast on your lunch at Eagle’s Eye Restaurant and have an extravagant three-course meal at Canada’s highest dining experience of 7700 feet. Scramble further up Terminator peak for a real adventure, and take in the astonishing views of the valley below.

Take an Excursion On Your Drive to Jasper, Alberta

Becca by the beautifully blue Bow Lake.
Seats on the bank of the Fraser river.

Day 13

  • Drive back along the Trans-Canada Highway towards Banff.
  • If you want to see Lake Louise, make sure to be up early – by the time we got there at 10 am it was too late. The car parks had been full since 6 am, but this may be better outside of the summer season.
  • A great alternative is Bow Lake, on the side of Route 93 towards Jasper. Here you can pull up on the side of the highway, and absorb the view, or take one of the small paths down to the lakeside.
  • Continue your trip on Route 93 to Jasper; we were staying in a lodge on the side of the Fraser River in Tete Jaune Cache, so we drove along the Yellowhead Highway west, following the Fraser River and taking in the impressive Moose Lake.
  • Have a delightful dinner at Tete Jaune Lodge and sit by the Fraser River with a glass of wine and a salmon burger – notice the bright red of the salmon!

You can't miss the drive back along the Trans-Canada Highway! Click To Tweet

Day 14

  • Drive back towards Jasper and follow directions to Maligne Lake and enjoy the dramatic drive through the mountains.
  • Hire kayaks from the boathouse and explore the lake from the water.
  • Take the Mary Schaffer hiking trail through the forest and look for wildlife, including a huge variety of wild mushrooms. Keep your eye out for bears too – but make sure you keep to the footpaths.
  • Grab dinner in Jasper and head back to your accommodation.

Have the Quintessential Tim Horton’s Experience in Kelowna

Day 15

  • Grab your morning pick-me-up at Tim Horton’s. It has to be done on a Canadian Road Trip!
  • Drive down to Kamloops, south on Route 5, and carry on to Kelowna and enjoy the mountain views and small Canadian towns as you go.
  • Check in to your hotel in Kelowna: try the Days Inn and then head out for dinner.
  • Savor your dinner at Ume, a small family-run Japanese restaurant found just off the highway into Kelowna’s city center. This serene little cafe cooks everything to order and the food is outstanding. Make sure you wash it down with a ramune soda!

Day 16

  • Get up early and head to Downtown.
  • Enjoy a super charming breakfast at Little Hobo Soup & Sandwich Shop. This eatery is perhaps the most memorable of the whole trip. You’re greeted as soon as you walk through the door by a waitress holding a coffee pot, and you leave feeling like you’ve gained a new family. The food portions are large and delicious, and you’ll want to never leave!
  • Explore Downtown, looking out for rainbow crossings and indie bookshops like Pulp Fiction. Continue down Bernard Ave to the Waterfront and take in the views. Don’t forget to visit the Bear sculpture – ‘Kelowna’ means brown bear in the Okanagan language.
  • Next, drive southwest to Vancouver and check into your accommodation – we stayed in an Airbnb near Trout Lake Park. This was a lovely neighborhood with great restaurant options on Commercial Drive, just a short subway ride into the center from Nanaimo station.
  • End the day off with dinner at Bandidas Taqueria, an entirely vegetarian Mexican eatery with an amazing atmosphere and the best nachos in town.

Stay A While and Tour Vancouver 

Day 17  

  • Relax on the last stop of your Canadian road trip and spot some whales on a whale watching trip from Steveston. We were picked up in a minibus from the center of Vancouver and driven to Steveston, a small fishing village past Richmond. Our bus driver gave us a tour and some history of the area.
  • We then got kitted out for the rib boat, in full Michelin-man style suits. We spent 4-5 hours out on the ocean and saw two humpback whales and three orcas. The captain took us all the way down to the Gulf Islands on the US border, which were beautiful sights themselves!
Looking down on the food court in Granville Market, Vancouver.

Day 18

  • Eat up for brunch at Medina Cafe (be prepared to queue) and try the Mediterranean inspired menu. A favorite of ours was the lavender chocolate waffle.
  • Make your way to Granville Island to see its impressive indoor market. Here you’ll find a sprawling mass of craft stalls and just about any food you could imagine – it’s completely undercover, so a perfect activity if it’s raining.
  • Walk up to Gastown, the oldest part of Vancouver, where you’ll find the famous steam-powered clock that whistles every fifteen minutes.
Rental bikes on the way ’round Stanley Park.

Day 19

  • Munch on some brunch at Nero Waffles. You’d be remiss not to get waffles on your Canadian road trip and were better than in Vancouver! Try the Banoffee – you’ll still be dreaming about them long after you get home. 
  •  Vancouver is very much an outdoor city, so the best thing to do is grab a bike and cycle a lap around Stanley Park to see the totem poles, and also catch a glimpse of North Vancouver from across the harbor. Unlike Toronto, there isn’t a Bike Share equivalent so you’ll have to hire from a store, but there are plenty to choose from. There are also numerous beaches which can be reached by bikes, such as Kitsilano and Sunset.

Day 20

The Tofu ramen at Ramen Danbo.
The infamous Japadog.
  • Although we all like to make sure we get the most out of our trips, make sure to spend a day winding down after a few busy days. Instead, wander the West End and Downtown neighborhoods and stop by a museum or the Bill Reid or Vancouver galleries.  
  • Here are two options for lunch: for the bao lovers, you can’t go wrong with Heritage Asian Eatery.  If ramen is more your style, Ramen Danbo on Robson Street is the place to go. Keep in mind the queue moves fast and works using the Japanese calling system – a fun experience to have under your belt, and they do incredible vegan ramen!  
  • Try out a food unique to Vancouver to end the day – the infamous Japadog: an unusual fusion of Japanese flavors based on the classic American-style hot dog (guess what our favorite cuisine is…).
  • For late-night entertainment, check out the independent Rio Theatre to see if they have any shows going on, though bear in mind that tickets can go quickly (this is best planned in advance). 

Head on Back Home

Day 21

  • End your Canadian road trip at the airport. Vancouver’s YVR airport is easily reached on the Metro system. If you have some time to spare before checking in then the McArthurGlen Designer Outlet is en route and might be a good place for you to stop off while you wait for your flight (Check out how to get last-minute seat upgrades for your flight while you wait!)

Have a great road trip, eh!

Plan, plan, plan – but ultimately, allow yourself the freedom to explore. While this was a very jam-packed itinerary, we allowed ourselves time off to be spontaneous and make our own discoveries. Plan the fundamentals, always research your food options, but allow yourselves to go off-piste and enjoy the adventure!

In the event you’re on a budget, remember to be creative with your accommodation and travel options.

With this in mind, when it comes to flights, book as early as possible. Lastly, have a budget for each day, but if an opportunity presents itself, take it! In this case, you can work the money out and rejig things if there is an absolute must-see!

Which places will you be adding to your Great Canadian Road Trip itinerary? Let me know in the comments!

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Planning a Canadian road trip? Need ideas on where to go? Include these must-see spots on your itinerary to guide you on your next adventure!
Planning a Canadian road trip? Need ideas on where to go? Include these must-see spots on your itinerary to guide you on your next adventure!

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