Flying into Lisbon or Funchal Madeira first?

I can answer the weather question. We were in Portugal for a week a week before Thanksgiving in 2023 and the weather was very comfortable. We were in Leiria and up north. I wore a light shirt, a light sweater, and a light jacket. I was always warm enough and sometimes too warm if we were walking in the sunshine. It was very moderate and enjoyable. The only time I really needed all 3 layers was when we were at the coast in the late afternoon/early evening.

Thank you! Yes I've read the weather in Portugal tends to still be warm in the "winter" months. It's good to get that confirmed 😊

It's extremely risky to wait until the last minute to buy any airline ticket. I have no idea how much demand there is for flights to Madeira in October, but airlines attempt to match seat availability to demand, so there's no reason to think there will be bargain-basement prices on tickets purchased shortly before the travel date.

Madeira is drop-dead gorgeous. I'm sorry you have so little time for this trip.

Hi I'm not sure what you are referring to. I'm purchasing my tickets soon.
Probably this weekend. I meant flying between Lisbon and Madeira and I'll be purchasing tickets for that flight soon too
I'll be staying a week total. Yes, thank you I'm looking forward to seeing my family's homeland ❤️🇵🇹

Couple things...

First, if you just have "a week" and you're coming from North America (and returning) it's a challenge to really make good use of your time on a trip to Europe (or put another way: get good value for your flight costs). Especially so if it includes both mainland Europe and an island way out in the Atlantic. Not saying you can't do it, just that it's not ideal: you spend a lot of money to fly all the way there and back, and you have just a handful of days to actually be there. For some of us, we would choose to defer the trip until you are able to be there longer. But it's up to you.

Second, given the above, it would be best to try very hard to be efficient with your time (you can't afford to be inefficient). Flying to Europe, turning around and then flying back 1/4 of the way across the Atlantic to get to Madeira, then flying back from Madeira to Lisbon, and then turning around again and crossing the Atlantic towards home...not exactly efficient.

Flights between Lisbon and Madeira are available year-round. And if purchased well in advance can be surprisingly cheap (I looked at random days in October and I'm seeing tickets as low as US$50-60 on multiple airlines). But every time you fly somewhere, you burn a whole day. You simply don't have very many days to burn, so each day you do dedicate to flying somewhere really take a bite out of your trip. Lisbon (and all of continental Portugal) are delightful, and worth more than a quick day or two.

You may not be aware of it, but you can fly nonstop between Toronto (Pearson) and Funchal (once a week on Azores Airlines "SATA")...but those flights only go from June to September (end of September). Any chance you could move up your trip a few weeks, to late September? That would make a big difference and give you a much better trip (and better chance at nicer weather, too).

Consider these options:

Move your trip up to late September. Skip mainland Portugal entirely for this trip, save it for another time. Fly direct from Toronto to Funchal, and back. Easy, efficient, even cheap. Or...

If you can not or do not want to move your trip up to late September...still skip spending any time in mainland Portugal, save it for another time. Fly from Toronto to the Azores (Ponta Delagada, on Sao Miguel), then connect to Funchal, without wasting much time. Do the same on the way back. It's just one more flight connection, but you concentrate your time all in Madeira, which seems to be your real destination (and you skip crossing the last 1/4 of the Atlantic....four times!). Be careful with this option, though, check your layover time in Ponta Delgada: on some days, the layover there is very long, on others, it's quite short.

If it were me, I'd try very hard to move the trip up to the 3rd week of September - that once-per-week nonstop flight from Toronto would tempt me on a short trip (it's like buying yourself a couple of extra days). Just check dates carefully to be sure you don't miss the last flight out to Toronto. It looks like Azores Airlines goes outbound (Toronto to Funchal) on Saturdays, and does the return (Funchal to Toronto) on Fridays

Hope some of that helps. Good luck.

You're very kind and quite helpful, thank you for your suggestions!
😄

There are lots of flights to Madeira from Lisbon, so you shouldn't have a problem (it's a really quick and easy flight, under 2 hours). I've spent 5 nights on the island. I'd recommend getting a car for at least a couple of days to go exploring.

I don't have an answer in regards to Lisbon or Madeira first, but make sure you have a night between the return flight from the island and your international flight in case of weather. Every so often flights get cancelled due to bad weather on the island. But, I do think Madeira would be a nice place to get over jetlag, so if it works, I'd do it first.

Thank you!
I'll have a guide in Funchal since I'm a tour guide myself and am meeting up with someone who lives in Funchal.
And yes, I'll definitely have one or two buffer days in between flights. And I'm originally from the west coast now up in Ottawa Canada.
Thank you!