Lisbon, Madeira and Algarve? In 2 weeks? Looking for a sanity check.

I cannot comment on the Algarve since I have not visited that region of Portugal, even after multiple trips. But I have been to Madeira and agree it's an easy flight from Lisbon. Madeira is gorgeous and you could even add more time there if you wanted. And can easily add more days to Lisbon. On my last trip I spent a week in Lisbon and day tripped. Sintra is lovely and you may want to take a look at Monserrate which does not get as crowded but has wonderful gardens. Perhaps consider Cascais instead of Nazare. And if the weather is not bad, you can day trip to Evora. Belem is good for a day, which is still technically Lisbon. I've been to Portugal in April, August, and December. I personally would not have a problem visiting in the fall, perhaps it would not be as crowded as the spring.

The Funchal airport is...umm...tricky. I think they built it by blasting the top off a mountain. I suspect if the weather is seriously bad, you won't be the one canceling.

acraven, that's an intriguing statement. Could you elaborate, please? Is FNC poorly run, or is it located in an area subject to floods, etc.?

It's a difficult runway and considered one of the most challenging in the world (geography). Can be prone to high winds and if that is the case, the airlines will not land and the flights will be canceled. It's one of the reasons why it's considered a good idea not to have an international flight the same day since, ie leave Funchal to Lisbon to.... but to leave a gap of at least one day. It's the only flight I have been on where the passengers cheered and clapped when the pilot landed. It can be rather thrilling. Easy Jet has many flights, so their pilots know how to get those planes down safely.

May I suggest you look at some of the many videos that are online about landings at Funchal airport? You’ll then understand. Due to it’s location and the wind coming from the mountains, Funchal is one of the most difficult airports in the world and pilots need special training before they’re allowed to land there.
I flew to Madeira a couple of years ago. Our landing was aborted at the last possible moment. After the plane gained altitude again, we circled around for an hour before trying another failed attempt. We then landed at nearby Porto Santo to refuel before returning to Lisbon. A couple of hours later, the winds were down and we did manage to land there.

In March this year, one of my colleagues had his holiday to Madeira extended by 2 days. During these 2 days, no plane was able to land on the island, so they were stuck.

Folks, I didn't know this about Funchal. Something to consider. If we go to Portugal, we'd still need another stop somewhere else, with nice weather in late October and a direct flight to LIS. I've looked at Sicily, Tangier, Malta. . . nothing really works. Or, we could end up going to Seville (again) and taking a bus to Faro.

I wouldn't worry too much about Funchal, just make sure you have a gap before your next flight, which you do have. Most likely you will have no issues. It's a lovely place and worth a visit and very easy from Lisbon. And if you happen to be unlucky, not a bad place to be stuck for an extra day or two. Just go visit a few more gardens.

Edit to add: Tripadvisor has a forum dedicated to Madeira. It's a very popular destination for the UK, so tons of information available on that forum that has more UK posters than this forum. There are not as many RS posters that visit Madeira as other locations and when I planned my trip, I needed to seek information on the other forum.

Setting aside the thrills that are sometimes associated with landing in Funchal, with the time you have, I'd probably just stay in continental Portugal - there's plenty in Portugal to keep you busy and happy for two weeks (have you been there before?). Or maybe hop to someplace else nearby that has fewer potential weather issues. Options that strike me as obvious would include Morocco (though certainly not Tangier - you want Marrakech or Fes), the Balearics (Majorca, Menorca, Ibiza), maybe Sardinia, Sicily or Malta, if you can put together reasonable flights that don't burn more than a day in transit. In late October, the weather will be starting to change but in any of these places you will still have a decent chance of mostly good-enough weather.

Looked at those videos of planes landing at Funchal. Ouch! Those cross-winds might be pleasant in summer but not in the end of October.