My husband and I are traveling to Portugal this fall and want to end our vacation the first week in October either in Madeira or the Azores. We are active people who like I explore but can't figure our which might be the better choice for four days. Suggestions from those who have been?
We've only been to Madeira, and not in the last ten years. I'd caution you that Mediterranean resorts tend to wind down for the season by October. When we cruised a small-ship from Rome to Barcelona, stopping only on islands (i.e. more central than Madeira) half the stores were closed for the season. This was nicely uncrowded, but it was sometimes hard to get a taxi, for example. Although we enjoyed our three nights on Madeira (then back to Lisbon to go home, as I remember ... ) it had (well before the Great Recession) a feeling of past era grandeur as a British sun/sea resort, now more of a backwater. We stayed at modernized cottage colony that was very nice, but places like Reid's Hotel had a "dinosaur" feeling to them. Check whether your credit card covers car rentals on small islands, BTW. I am sure Madeira is greener than the Azores, but it's no Bermuda or Tahiti. Do you know the hotel pools are placed just above the water because there are virtually no beaches on this rocky island? In some cases you cross the street and take a second elevator down the cliffside to the pool.
That said, the llevada paths were beautiful walking, with basic shoes and no rock-scramble danger at all. You should check the October climate in Madeira - we were there in the summer. When we hired a car and driver to tour around, he did a good job, but the mountaintop view was completely fogged in that day. Oh well!
Have you explored other, mainland romantic locations, like a Pousada or luxury hotel? I wish I could tell you the royal hunting lodge of Bussaco Palace Hotel was great, but it was more of a "dinosaur skeleton" than a "dinosaur". But some of the gut-renovated monastery-Pousadas were lovely, and plenty to do on foot in the daytime, like (AFAIR) Guimares. I think there's a pousada in special villages like Óbidos. But that might be too isolated after two nights, despite the "Rick Steves" chance at walking the streets after the tour busses have gone!
Tim, thank you for your thoughts and suggestions.
Al
Back in September 2014 I posted "My 2 cents about visiting the Azores" specifically regarding Sao Miguel and Santa Maria. Since then others have asked questions in their posts/titles about the Azores, you could read them as well for my responses. I have been there almost a dozen times, Madeira only once in 2010. The destinations are very different! I would not want to steer you to either without you doing a little more research here on this forum to see what suites your taste... That said, if I can answer any specific questions let me know. Take care!