Spain, Portugal and southern Italy

It depends on how in-depth you want the trip to be. 12-15 days in Portugal will allow you to see a great deal, but you'll still be leaving out some very nice places. In the other two countries you will be much more limited. I tackled Spain in 2016; I spent 89 days in the country (albeit without a car, which makes me slower) and I did not include Andalucía. I'm going back this year to see Andalucía and a few other spots I missed, like Valencia and Palma de Mallorca. I haven't figured it all out yet, but it looks like it will be another 45 days or so. And I have absolutely no interest in several things many travelers spend considerable time on: beaches, wine and palaces.

Since Italy is the farthest afield (though traveling on the ground between Spain and Portugal is a significant challenge, as you will find out), I'd suggest focusing first on Spain. Get a comprehensive guidebook and did into the chapters on areas not already on your mental target list. Are you OK with skipping the Basque Country? Galicia? Everything in Catalunya except Barcelona? Two weeks is not really enough time for Barcelona-Madrid (Toledo and Segovia day-trips), Cordoba, Seville and Granada. Based on how you handled Germany, I don't think you'd be happy with 14 days in that set of cities I listed, so you could either pare the list back, focus on a small section of the country, or drop Italy from this trip and use that time mostly in Spain. That would still not allow you to cover the full extent of the country, but the omissions would be less painful.

As for Italy, I don't even know what amount of time I'd suggest there. Maybe six months (not legal without a visa) would be a decent start. Again, it's all in what you want to see. Two weeks would be OK for Venice-Florence-Rome, and you could do a side-trip or two in Tuscany without rushing. But you're missing the Dolomites, the lakes, Bologna and all its side-trips, Verona/Vicenza/Padua, Turin, Milan, Naples and environs, the Amalfi Coast, Puglia, Sicily (worth 3 weeks by itself).

Edited to add: Even Portugal, small though it is, could probably fill all your time if you included Madeira, which is drop-dead gorgeous but would require flying in and out.

I left out, to be concise, that we have visited Italy on two previous trips including Rome, Florence, Venice, Milan, Lake Como, Padua, Verona, Assisi, Cinque Terra and a few assorted places in between. Thanks for your input We are most appreciative for your help.

Aah. In that case, looking purely at Italy, you might reasonably tackle the area around Naples/Amalfi Coast and perhaps Puglia, though 12 days might be a little tight for me. Hard to know since I never have the use of a car.

Spain
Barcelona, Madrid (day trips to Toledo and Segovia), Grenada, Cordoba and Seville.

Portugal
Lisbon (day trips to Evora, Sintra), head to Porto (in route stop in Obidos, Batliha, Navarre), Douro River Valley (take cruise for a week or use train or shorter cruise).

First of all, what months of the year are we talking about. Portugal is on the Atlantic coast and tends to be colder in spring - this I know because I'm currently planning a trip there for late May, even then the temps look to be quite mild based on previous years' data. Andaluciais the hottest driest part of Europe (and Madrid is similar) . Weather from February to April is generally mild to warm with lots of sun and relatively little rain, Barcelona too. Summer is extremely hot in Andalucia and I wouln't recommend going then - June through mid-October.

Portugal - I've got 22 days on the ground and planning a loop from Lisbon to Evora to Porto by car, then bus/train in the coastal areas back to Lisbon.

Spain - In the last 5 years, I've been to Spain 3 times, each for over 3 weeks - Madrid, Andalucia, Barcelona, Valencia. The second and third trips included returning to some cities, but only revisiting a very few favorite sights (the Mezquita in Cadiz, the Prado and Thyssen museums in Madrid, the Alcazar in Sevilla).

Italy - Since you are looking at the south I've stayed in Naples, Sorrento and the Amalfi Coast in February and there were few tourists. After reading comments from others, I wouldn't want to be there much later in the year - maybe April and early May, before or after Easter's crowds. I spent 2 weeks in April-May in Sicily, mostly with a car, and had a hard time planning because it was so hard to pare down the list of places I wanted to see.

You'd likely fly from Portugal to Spain (there are no good ground connections) and then from Spain to Italy.

I could happily spend another 6 weeks in Spain or Italy.

Although weather is a consideration in our travels it hasn’t been a deciding factor. We have dealt with rain, both hot and cold temperatures as well as wind(60 mph at Lands End). Generally our time frame is early May to mid June. We’ve dealt with train strikes in Germany and “language barriers” in very few instances. Road construction in Nice and World Cup crowds in Milan and Paris. We’ve had fun and blessed by the people we encountered.

May is probably good in most of Spain. There are festivals in Andalucia that are worth seeing, but there will be crowds and high prices. I'd try to end in Portugal. I think you'll find more than enough in Spain and Portugal, adding Italy will just mean skipping a lot of Iberia.

If you want to go to Portugal this year, it appears to be hard to find vacancies late May to early June.

Why? Although vacancies maybe hard to find we usually find what we need. We are not opposed to returning to places we’ve “missed”.

Priscilla found that many of the places she wanted were fully booked when she was doing her bookings a couple weeks ago. I've started looking at places and have seen "one room left" notices or only more expensive rooms available.

I'm a budget traveler. Last night I spent well over an hour trying to find a room in Lisbon for 3 nights at the beginning of June. I'm struggling and it looks like I will have to prepay for either of the affordable places I've found that meet my minimum - private bath, reasonably good location, clean, somewhat quiet.

Essentially you are planning a fortnight in each of Italy, Portugal and Spain. That is eminently practical. Lot's of people make their main annual holiday a couple of weeks in just one of those. All you are intending is to join them up. Lucky you. Sure, you'll spend some time travelling between the countries on two days out of the 40+ available, but a lot less time than if you made three separate trips each beginning and ending in California (which I'm guessing is what CA means). So yes, practical and desirable.

Naturally you could spend six weeks in just one country or in just one part of one country. But splitting the time between the three would be fine too. There's no rule that says you have to stick to one country and see it all before sampling another one. It's not as if you are trying to do the three countries in three days.

In reality, flying between Granada and Naples is only an hour or two more than flying between Granada and Barcelona. Getting to the airport, security, waiting around, etc is the same for either destination.

To do the detailed planning you'd need to know gateway airports for you to & from Europe. But once in Europe there are lots of options. For example, if you started in Rome and headed south, from Bari you can fly to Barcelona. Then head south in Spain to end in Sevilla from where you can fly to Porto. Then visit Portugal to end in Lisbon. That's a but zig-zaggy, but there are lots of ways to organise this, once you decide to go for it and where you can fly into from home.

Planning is one of the best parts for us...finding rooms and making connections is part of the challenge.
Your comments are most appreciated. We love the challenge and adventure of it all.