Madeira or the Azores in late September?

There are never any mobs of tourists in the Azores, except when a cruise ship, or multiple ones, is docked in Ponta Delgada, Sao Miguel. And only in that city might there be crowds walking throughout the compact area near the harbor.

September sees less tourists than during the summer. Most will be visiting from other European countries.

With only one week, realizing there are nine islands in the Azores to choose from, I would pick Sao Miguel only. I generally base myself in Ponta Delgada. The weather should be nice at that time of the year you will be visiting.

You could easily spend a month or more just on Sao Miguel and not see and do everything, especially if you enjoy hiking. Pace yourself with any plans you come up with.

I visited Madeira back in July of 2010, and even there I never felt as though anywhere was too crowded. However, my experience in the Azores since 1994 is what what I know best.

At the top of this Portugal forum is where you can access my Freemium Azores guide for more information. This section of the much larger (paid) Azores guide is free to read. All the logistics for travel to the islands and among the nine islands are in the freemium.

Let me know if I can help further.

We have visited the Azores twice and Madeira once on cruises.
Both were awesome. Both are very scenic places with unusual flora and fauna. If you waned to spend a lot of time there, I would go with the Azores.

I have been to both and my recommendation is definitely the Azores. I have been to Sao Miguel 6 times at different times throughout the year. Sept should be lovely weather and few tourists. My favorite place to stay is Quinta das Acacias - lovely selfcatering cottages set in a beautiful garden setting in the tiny village of Livramento just a short drive from Ponta Delgada. Bonita & Ed are the owners and offer great recommendations.
There are so many things to do: horse back riding & kayaking with Quinta da Terca, soak in hot springs at Ferraria and Dona Beija, have a cozidos meal at Calderias do Volcoes in Furnas, visit Cha Porto Formosso tea plantation, sample the local liquors at Fabrica de Licores Mulher de Capote, watch pottery being made at Ceramica Viera, shop for fresh fish, veggies & cheese at the farmers market in Ponta Delgada, walk in a lava tube at Gruta Cavao.
If you like to hike, there are dozens of fabulous hiking trails, such as hike to the lighthouse in Nordeste or hike into a waterfall.
Be sure to rent a car and drive the entire island. The views are stunning and the tiny fishing villages are very picturesque. Logoa de Fogo is stunning. Great sea glass on the beach in Moisterios.

We were on Madeira for 7 days during the last week of November 2022. The weather (20-22C highs and no rain) and the levada hikes were fabulous. Even went swimming in the seaside pools. We rented a car to get around. We did plan our Pico Ruivo hike right after sunrise and on a day with no cruise ships. Fanal forest was great for photos. Lots of hiking and exploring on Madeira and we could have easily spent another week. Quick 1.5 hr flight from Lisbon and inexpensive. If you want a great beach and day trip, a boat ride to Porto Santos is ideal. Overall, Highly recommended!!

Hi, sstclaire,
I've just returned from the Azores and fell in love with the beauty and warmth of the islands. Of course my vote is Azores, though I haven’t been to Madiera, so, it's only based on what I know.

I posted a trip report with some photos, if you're interested. Just go to the "tips and trip reports" section and you should be able to find it.