Italy/Spain/Portugal in September or October

I initially thought you were planning way ahead for a trip to will occur in 9 years, then realized it will be your first time back there in 9 years.

With only 2-3 weeks, I’d stick to one country. If going to Spain I’d narrow that down further to a region or two. There is no shortage of places you could visit. To me, the decision is whether to go to the popular destinations (Madrid, Barcelona, Sevilla, Lisbon, Porto, etc.) that most first time visitors go to, or head to some smaller less visited yet equally interesting secondary sites.

Thanks so much, jaimeelsabio.

I see now how I made it confusing about when we're planning this trip, LOL :)

I'd also choose one or the other (lumping Portgual and Spain since they are adjacent, but not all three). I've been to Italy seven times, never run out of itineraries. Spain I have visited four times and I know it'll take my lifetime to see the rest, but mostly I avoid plane trips or really long train rides within my trips, so I would not stretch the itinerary but instead concentrate it.
Airfare schedules and prices would determine how to do it, if you want to do both. Skyscanner is a good site to search intra-Europe flights. Portugal and Spain are not as well linked by transit as you would think, but with that amount of time, you could fit parts of both in.
Because the Amalfi coast and Cinque terre have been so popular in recent years, I would encourage you to check out some areas with similar gorgeous coastal scenery: Cilento coast, Puglia, Marche (the bit south of Ancona), other parts of Liguria and the Tuscan coast. And Sicily alone would make for a fantastic three week trip--in the time of year I would most like to go there too!
In Spain, my favorite coastline has been in the Basque region. It would be great to visit Andalucia when weather is not so hot.

What are your interests? Seems like perhaps countryside & walking, seeing the water based upon your 2 Italian ideas? The later in the year, the slightly cooler weather and slightly smaller crowds. I would pick October. Agreed, skip Cinque Terre & Amalfi Coast unless you want to stay outside those areas, north of CT or south of AC, take ferries along coast, but really there is so much else to see in Italy, why go where the crowds will congregate? You could

Any of these 3 countries could easily keep you busy / entertained and enjoying yourselves. Anytime you fly between cities, you lose most of a day. What about northern Italy? You could fly into & out of Milan, take train to Lake Como, & perhaps Bologna and it's amazing environs & lots of food tours? Or Southern Spain, OR Sicily. There are so many TR's and ideas if you use the search bar above to narrow down your choices.

Agreed, pick one country. But if you REALLY want to do 2 countries in 2 weeks, book a "multi-city, into Madrid for example, out of Lisbon. Price may help you decide. I prefer Google Flights, gives an excellent overview & I've actually found United trips that were not listed on UA website. Good luck!

I appreciate all of this info so much!

I'm going to focus on Spain & Portugal this trip. I can see that tackling 3 countries in 2 weeks is a bit much...I'm going to assume we'll travel to Europe again and it won't take 9 years the next time!

Good call--there have been a number of posts in the Spain forum asking about combining Spain and Portugal, so I would peruse those to get some ideas on itineraries and transit. Good luck!

There have also been some posts on the forum about the severe drought in southern Spain and the impact the drought has had and is projected to have on tourism. I can't find the specific posts but you may want to consider the drought and its impact.

Thanks again, all for this terrific info! I'll check the Spain forum for more ideas and thank you for mentioning the draught in Southern Spain...I did not realize :(