My wife’s sister lives in Toronto and her father was visiting from Venezuela so we decided to make the trek to Toronto over Labor Day, which is also a holiday in Canada.

Flight Planning

There are several flights from Boston to Canada. Most fly into Toronto’s Pearson airport which is the larger of the two airports. It’s located away from the city so we’d have to rent a car if we flew in there. There is also another airport, Billy Bishop Toronto Airport which is on an island in the center of Toronto. Lesser-known Porter Airlines files into that airport. My wife and I have each flown them before individually but never as a family.

Checking on flights.google.com flights on Porter were several hundred dollars cheaper and would allow us easy access to stay in the heart of the city. This would preclude us from needing to rent a car and avoid the sky-high parking prices as well. We could have rented a car and stayed in the suburbs, but we preferred to be in the heart of the action.

We ended up finding a flight first thing on the Saturday of Labor Day weekend arriving around 11 am and returning Monday on a 7:30 am flight. The timing was acceptable as it would have cost significantly more to get flights at other times. People apparently don’t like morning flights on weekends/holidays and prefer to sleep in so we took advantage of the lower price.

Overall the tickets were still just over $300 each which is far from cheap, but they were more palatable than the $500 each we were seeing with other airlines. We purchased the tickets on the Porter website as two different itineraries as suggested by Google Flights. Purchasing a round trip ticket would have cost a non-trivial amount more. Normally it’s better to purchase a round trip ticket so if you have to make changes on your outgoing flight, you only have to pay the change fee twice, but with two one way tickets they were two separate trips.

In this case, I purchased Basic Economy tickets which didn’t allow any changes anyways so ultimately it mattered a lot less. Generally, I vigorously avoid Basic Economy at all costs due to the restrictions, but for this trip, I was looking to save the money. The difference in cost was considerable. I also didn’t pay for seat assignment since it was a short flight and the times we had been on the airline before the flights were not very full. We’d keep our fingers crossed. It was only an hour of flight time and the kids were more than big enough to sit alone. If you need to sit together, do everyone else on the plane a favor and pay for the seat assignment. Being the last ones on a full plan and asking people to switch seats (when you likely got assigned a middle seat) will not make you many friends.

I paid using my Citi Prestige card to take advantage of the 5x points per dollar as well as the trip cancellation/delay insurance it provides. Due to changes on the card those benefits were ending on September 1st, before the trip ended. Since I bought the tickets before the coverage ended that coverage still applied. It’s based on the date of purchase not the date of travel so I wanted to take full advantage of that. This insurance gave me more confidence in buying the basic economy tickets as it could help if we ran into issues.

Hotel Planning

Per usual we’d look to stay in a Marriott Hotel in order to utilize my wife’s Titanium status for free breakfast. There are a number of nice hotels in the Toronto area but we were immediately drawn to the Sheraton Centre Toronto. Not only was the AAA rate attractive, but the hotel also had a lot of different room types which meant there would be more opportunities for a complimentary upgrade. It’s in the center of Toronto in a vibrant area and my wife had stayed there during her sister’s wedding. The property also has a club lounge (for breakfast) and an indoor/outdoor pool.

The cash prices were just over $200/night USD for rooms with two queen beds and there were lots of room categories that we might be upgraded to so we booked two nights on the lowest refundable AAA cash rate.

Transportation

The plan was to spend our arrival day in the city where my wife’s family would join us for the afternoon and dinner. We’d then spend the Sunday at their house in the suburbs. Originally I planned to rent a car for the day by picking it up in the morning and returning it that same day. I figured it would be cheaper than a taxi/Lyft/Uber. I figured incorrectly. Rental cars for the same day were extremely limited. They had to be returned by 6 pm which wasn’t going to work. I then checked into renting a car overnight and pay for parking at the hotel. To do that I would have to trek out to the Pearson airport and return it there the next day. Logistically that was difficult because we had an early flight out of the other airport that same day. The rental was also going to cost over $250 which definitely wasn’t going to work.

I then checked to see if Lyft or Uber were available in Toronto. The last time I had checked only Uber Black Car service was available and was pretty expensive. I was happy to see that both Uber and Lyft were available with all the options we get at home in Boston. That sealed the deal for us to use that for our trip to and from the suburbs to visit family.

Phones

Since my wife’s cell phone service provider, Cricket Wireless, works for free in Canada she could just use her phone normally. My service provider, AT&T Wireless, owns Cricket Wireless but despite having a much more expensive plan, I don’t get free roaming to Canada. I would have to use the data card we’ve used on other trips from KeepGo.com if I wanted to use any data. We have a spare phone that Tomatico uses to take pictures on vacations that also has a similar data card installed. We’d be bringing that phone with us as well. We didn’t expect to use such data as the prepaid data that remained on the cards we had would work the limited use we had planned.

With everything set, we were ready to head to Canada, eh?