On a whim I booked a last minute one week Caribbean vacation with the departure 3 weeks from now. I’m sorted for what I plan to pack (I think!!!) but I’m fussing about my ‘in transit’ outfit.

Although I live in a small town 100k from Toronto and the Big Airport - I figured out that I don’t have to really experience winter weather from the moment I catch the train at our local station until I get off the Mega Bus at the end of our trip! There will be lots of walking, though:

Board train for 1 hour trip to Union Station
Walk about 1k and catch the UPS (Union to Pearson AirPort Express train)
Walk through airport tunnels to Hotel (where we will spend the night)

Walk through tunnel from Hotel to airport where we will be processed
Board plane and 5+/- hours later deplane in the Caribean!

For the return, the trip is reversed, with the exception that the flight is shorter, and once we land back in Toronto….
Catch the Mega Bus at the airport for the 1.5 hr ride to the drop off point in our home town.

We will likely have snow during the first half of February, and temps will likely be in the -10 to 0degC range. I want to travel light, and this includes enroute. I figured thick soled ‘dad sneakers’ (see below) will work well, since I often wear them through winter if the sidewalks and parking lots are clear of snow - and probably a short puffer. But, what to wear when I’m essentially transitioning from below freezing temps to 28degC/82degF? Linen pants? Athleisure joggers? A button down shirt with a light sweater (that can be removed).


What would you wear?