So: 2 weeks, a car, your loved one, 4 states, 2 countries, 2 provinces, and a limited budget? Welcome to the North American road trip!


My boyfriend Paddy and I decided that whilst we were on holiday in the USA, we'd like to take the opportunity to explore as much as possible...even if that meant hopping across the border into Canada.

We'd previously spent a few days together in New York after my tour ended (read about that here) and were due to fly back from Chicago as we wanted to visit there too. We had 2 weeks in between, and both of us wanted to explore areas of the country that we'd never been to before - so that meant New England, essentially!

The Route:

  • Boston, Massachusetts
  • Portland, Maine
  • White Mountains, New Hampshire
  • Burlington, Vermont
  • Montreal, Quebec
  • Toronto, Ontario
Planning a road trip that spans across a lot of land takes a bit of effort, and a lot of planning ahead. We decided the big cities we really wanted to see were Boston, Montreal, and Toronto, before heading south to Chicago, but we wanted to make sure we got a good dose of New England on the way. So, after a lot of research, we planned stops along the way in Maine, New Hampshire, and Vermont, depending what made the route easier, what sights there were along the way, and where we could find nice, but not too expensive places to stay.

The Transportation:



We hired a car through Alamo, which is a car hire company in the USA and Canada. We had to pay a couple of premiums on top of the original price because we're both under 25, and we were picking up and dropping off the car in two different places. Overall the total for 2 weeks came to about £150-200 between us. You can pick the size car you like depending on how much you're willing to pay, how many people there are, and how much luggage you have. We ended up going for the second smallest and then upgrading when we went to pick up the car as it just wouldn't have been big enough for all our stuff!


The actual car you get isn't up to you - you only pick the size. Luckily though, we got given a Dodge Dart, which was a really nice and spacious car, so we were chuffed!


The Accommodation

We stayed in a mix of hostels, hotels and an AirBnb on our stay, depending on what worked out cheapest and how long we were there for. For instance, we stayed in a hostel in Boston as we were there for 4 days, but at a hotel in New Hampshire as we were part-way through our journey and wanted to treat ourselves to a nicer bed and room for just the night.

Bear in mind though that the biggest cities will be more expensive no matter what; so unless you want to spend more money on a hotel there, I'd recommend exploring hostels or possibly AirBnbs as they're much cheaper and can be just as comfortable. Also, lots of hostels are really great at giving recommendations of places to visit and/or eat, and the employees usually know of the best deals!

We stayed with HI Hostels in Boston, an AirBnb in Portland, The Bernerhof Inn in New Hampshire (which was beautiful, I absolutely recommend), and the Planet Traveler Hostel in Toronto. I can't quite remember the name of the one we stayed in in Montreal, I'm afraid - and a quick Google hasn't brought up any old memories so it may well have changed its name!

The Trip

We spent 2 weeks driving 740 miles from the north east coast moving out towards the midwest. It was one of the best trips I've ever done, and doing it together as a road trip made it even more fun! If you can do a road trip while you're in that part of the world, I really recommend that you do. It's a great way to really explore the country, and find parts that you didn't know existed.

Boston, MA






Portland, ME



White Mountains, NH




Burlington, VT





Montreal, QC





Toronto, ON






At some point I'll be doing individual posts about each place, but if you have any questions or if I've missed anything out, leave a comment below or feel free to drop me an email! :)

Happy driving!