Azores vs Maderia

Madeira is upscale and more expensive. Also, it seemed to have more tourists.

The Azores have several islands and the islands are relatively large.
The scenery is great on both, but I like the Azores more.
Not sure your want to spend all 10 days in one place, consider splitting.

What time of year? I was researching Azores for winter months to escape Canadian winters and the travel show representative says Maderia is better in winter as Azores gets pretty constant Atlantic winds.

Haven’t been to Madeira but went to Sao Miguel a few years ago and explored the entire island with a car. It was absolutely beautiful. We stayed in Ponta Delgada which was walkable with excellent restaurants. We considered visiting other islands, but decided to fully explore one rather than see a little multiple islands.

The trip was a full 2 weeks on the ground which included Sao Miguel, Evora, Sintra and Lisbon.

I recommend the Azores over Madeira. I’ve been to Sao Miguel 7 times and find new sites & interesting things to do and see each time. I find the Azores less touristy and more reasonably priced. There are so many things to do and see on Sao Miguel, such as horseback riding, kayaking, hiking, whale watching, tea & banana plantations, swimming/soaking in hot springs, eating cozidos & enjoying fabulous cheeses & wines.

Thanks! How many days are good enough for Sao Miguel?

Just returned from a family trip (Lisbon, Porto, Madeira & Sao Miguel) with two teens.

In terms of Azores vs. Madeira, we liked Madeira way better. We felt there was way more to do and explore there. However, it is a big cruise ship place (Sao Miguel also has its share of cruise ship stopovers), and we stayed in Funchal, Madeira, which is the capital. Still, there are so many parts of the island to explore we would like to go back. We went hiking, the landscape is incredible and there are dolphin and whale cruises you can do, botanical gardens, and so much more in Madeira. Many more options for food here too.

We were disappointed with our time in Sao Miguel and we stayed in Ponta Delgada. Overall I think we found it kind of boring. Maybe we should have visited other islands? Not sure. It's pretty, and the nature is amazing, but we found the island overall a bit disappointing. I think we would probably just should have extended our stay in Madeira and skipped the Azores, honestly. The weather in Sao Miguel was the worst we had on our whole vacation. Rain, cold, gray, then some sun here and there, but given where it is located not surprising. We were told the Azores are trying to build their tourism industry while Madeira seems to be well-established, if that makes sense.