Azores or Madeira as a Component of a Three Week Portugal Trip?

Have been to the Azores (spent ~3 weeks there, loved it), haven't been to Madeira (yet). Have been to mainland Portugal several times (loved it, too). It's true that there are plenty of direct flight options to the islands. But I would offer some caution on the planning/logistics.

Biggest question: How long is your trip? Getting from mainland Portugal to/from either island group is going to burn a full day each way, so you're going to lose two full, usable days out of your time on the mainland. If you're going to Portugal for a month or more, and you lop off a few days for the island side-trip, you probably won't miss those few days. On a shorter trip, consider it carefully. I think most visitors underestimate both how large/diverse mainland Portugal is, and make the same mistake for the islands. Count your days carefully and be realistic about how much usable time you really have.

For example, we were in the Azores for just shy of 3 weeks, and we didn't get to everything we would have liked to see (we look forward to going back). I think many (American) tourists make the mistake of trying to "do" the Azores in a day or two, which leads to disappointment - there's a lot to see and do, more than many people think. We spent a full week on Sao Miguel (didn't get to everything); 10 days on Sao Miguel would have been about right for us, even on a fast-paced trip. And the other islands each has something unique and interesting, too (there are 9 islands, we visited 6 of them). Bottom line: I think the Azores are worth more time (a lot more) than most people expect. But that's also true of mainland Portugal, thus the dilemma. Count your available days carefully, and maybe save the Azores or Madeira for another trip when you can do them justice.

The real question is, how much time do you really have, and how much of mainland Portugal do you want to try and see? Hope that helps.

I always recommend to visit the mainland separately, no matter for how long.

You could spend months visiting these nine Azores Islands and not see and do everything. The same goes for the mainland of Portugal (been there five times).

I spent a week in Madeira and that seems like a good amount of time on that one island.

Azores Airlines plans to fly JFK to Madeira some time in 2024, and also Ponta Delgada, Sao Miguel to Faro (Algarve). Knowing what I know, having flown with Azores Airlines (formerly SATA Internaçional) and the current SATA Air Açores for almost 30 years, is they are spreading themselves too thin.

You will have more than enough on your plate with Lisbon, Porto, and everywhere else on the mainland.

Have a wonderful trip!

We flew to Ponta Delgada first, stayed in São Miguel for a few days before continuing to Lisbon.
Returned home direct from Lisbon.

This is the most efficient itinerary.
Azores Airlines flies from direct to Ponta Delgada from different airports in North America.

Thanks for all the useful input. Subtracting our outbound and return flight days, we have a total of 18 full days for sightseeing and/or transfers within the itinerary (ie, Lisbon-Porto, etc). My first cut at an itinerary usually echoes those of the RS tours, and that approach has served us well for most of our European trips, although we typically extend the time in the major cities beyond what the tours use so we can explore a bit deeper. We also tend to favor longer stays over one night stops, so we frequently drop one night stops unless they are compelling enough to stretch to two or more nights. Beyond that, the details of our itinerary is a bit fuzzy, so I clearly have some homework to do, with or without an Azores addition.

I managed to add two more days/nights to our trip date range, so we now have a total of 24 days, with 21 of those days available for the trip itself (ie, after subtracting out the outbound and return flight days). With this allocation, I then developed two itineraries: one with a week in the Azores, a second without. Here is the Azores option:

1. Fly LAX-CDG
2. Fly CDG-LIS, train to Evora
3. Evora
4. train Evora-Lisbon, overnight in Lisbon
5. Lisbon (city tour)
6. Lisbon (day tour-Alcobaca, Fatima, Obidos)
7. Lisbon (city sights)
8. Lisbon (day tour-Mafra, Ericeira)
9. Lisbon (city sights)
10. Lisbon (day tour-Sintra)
11. fly Lisbon-Azores
12. Azores
13. Azores
14. Azores
15. Azores
16. Azores
17. Azores
18. fly Azores-Porto
19. Porto
20. Porto
21. train Porto-Coimbra
22. Coimbra
23. train Coimbra-Cascais, overnight in Cascais
24. fly Lisbon-LA

Madeira is also under consideration (in place of the Azores), especially if the weather is more settled.

Here is the mainland option for the same date range:

1. Fly LAX-CDG
2. Fly CDG-LIS, train to Evora
3. Evora
4. Evora (rent car, day trip to ?)
5. drive Evora-Monsanto, lunch in Marvao
6. Monsanto
7. drive Monsanto-Pinhao, overnight in Pinhao
8. Pinhao
9. drive Pinhao-Porto, overnight in Porto
10. Porto
11. Porto
12. drive Porto-Coimbra, lunch in Aveiro, overnight in Coimbra
13. Coimbra
14. drive Coimbra-Tomar, overnight in Tomar
15. Tomar
16. Tomar
17. drive Tomar-Sintra or Cascais
18. Sintra/Cascais
19. return rental car, train to Lisbon
20. Lisbon
21. Lisbon
22. Lisbon
23. Lisbon
24. fly LIS-LAX

This option has a lot more driving, although we would have a car on the island for a week for the first option as well.

In April we went to mainland Portugal then flew from Porto to Madeira for a few days then flew from Madeira to Sao Miguel in the Azores for a few more days. Obviously, the way we travel (packing a lot in) is not for everyone! I personally preferred Madeira over the one island in the Azores that we visited. I think there would be plenty to do/see in Madeira for a good 5 - 7 day trip.

Our time on the mainland was just in Lisbon and Porto. It was manageable for us to hit those two cities and then travel to islands. I wouldn't recommend trying to cover much more of the mainland than that if you are trying to add an island stop too. The constant transporting here and there, adjusting to new hotel, etc. gets a bit exhausting. Have fun!