PLease Help With Itinerary

If you have a month you cannot miss Barcelona. You could drive to Valencia within four hours before moving on to Granada, but it would be a little over five hours from Valencia to Granada. Perhaps you could stop mid-way between those two to break it up. You could always follow Rick's sample itinerary of Spain and adjust from there.

If Spain and Portugal are your focus then Gibraltar is neither. It offers a mostly British experience.

A couple of lists here with descriptions of highlights in both countries.

http://www.planetware.com/tourist-attractions/spain-e.htm

http://www.planetware.com/tourist-attractions/portugal-p.htm

Your criteria of '4 night minimum stays' means of course a maximum of 7 destinations. (Yes, I was good at maths). The list then pretty much writes itself...
Madrid
Barcelona
Seville
Granada
San Sebastián
Porto
Lisbon

I should have mentioned that we've been to Barcelona... I was concentrating on the area I mentioned and haven't been too and wondered where we should stay and what we shouldn't miss.
Sorry about that,
Jean

To figure out how far you can get by car in 4 hours, you can use ViaMichelin. Be aware that folks generally feel the time estimates are a bit optimistic, and of course they do not include any stops. The drive from Quarteira to Seville will be OK, timewise, but I'm not sure how you're going to manage a more northerly cross-border trek within 4 hours without an intermediate one-night stop. ViaMichelin estimates Madrid/Toledo to Lisbon at 6 to 6-1/2 hours.

OK then, looking exclusively at your list, and linking them up to make a sensible journey over 4 weeks, necessitates a few stays of less than four nights unfortunately.

Madrid (4N)
Caceres (2N)
Evora (2N)
Lisbon (4N)
Quarteira (3N)
Seville (4N)
Malaga (3N)
Granada (3N)
Toledo (3N)

Take into account Semana Santa (last week in March 2018) which is huge in Andalucia. Decide whether you want to avoid it (lots of crowds and high season prices) or immerse yourselves in it. I would recommend Malaga for 4 days, then maybe end in Granada with their big Easter Sunday procession. Sevilla is the most popular city that week, but much as I love Sevilla, I didn't find Semana Santa nearly as interesting or enjoyable there as in Malaga. As big or bigger than Semana Santa is Feria in Sevilla, April 15-22, 2018. Again, decide if you want to be part of it or steer clear of it.

With only 4-night stays and no more than 4 hours to drive from place to place, it's a puzzle. You list 7 cities (the Alhambra is a sight in Granada) without Madrid. 4 weeks = 28 days (4 nights x 7 towns). Are you skipping Madrid? Your longest drive is from Madrid to Lisbon. It's a really really bad idea to drive after a long-haul flight. What you could do is take the train from Madrid to Toledo. Then either rent a car in Toledo (in fact it's a little less driving time than from Madrid), or take the train back to Madrid and rent the car there.

viamichelin.com estimates the fastest driving time from Madrid to Lisbon at about 6.5 hours (net). Quarteira - check when the Algarve "opens" for tourism. Most of it is shut down for winter. From the same source, net driving time from Quarteira to Sevilla is less than 4 hours, but to Malaga is about 5 hours. I don't know where you'd end your trip that's "near" the airport. It's 5.5 hours drive from Sevilla to Madrid. Toledo is the only place on your list fits the bill.

We intended to stay in Madrid on arrival for 1 - 2 nights.
Not sure if we should instead depart Canada Mid-March to Mid-April so the weather would be a little warmer but this would entail being there over Easter. Not interested in areas with large crowds.
Thanks for all your suggestions; will now have decisions to make!
Jean

Ok, what about this new itinerary?
Fly into Barcelona 3 nights can always see more of this city
Madrid 3 nights
Caceres 2 nights(or Madrid to Porto 3 nights stopping somewhere along the way then Lisbon?)
Lisbon 3 nights
Quarteira 7 nights
Malaga 10 nights
Toledo 2 nights
Madrid Airport 1 night
Fly home...
Get to see more and get non-stop flights
Jean

Jean, are you sure you want to spend such a huge percentage of your time in coastal cities/towns? I admit I've never been to Malaga or Quarteira, but I am doubtful that there's enough to sustain the typical tourist's interest over an extended period, by comparison to places not on your list like Cordoba, Ronda and the white villages. You haven't mentioned seeking a totally relaxed golfing vacation.

Caceres would make a nice stop, though I suspect it may be pretty quiet in March. The town of Trujillo (closer to Toledo) is also worthwhile, but the historic area in Caceres is larger. Merida, south of Caceres, has significant Roman ruins; I think they're considered the second best in Spain, after those in Tarragona. I believe it will be a good bit cooler in that part of Spain (Extremadura) than on the southern coast at the time you will be traveling.

Madrid has quite a lot of good side-trips that would justify a longer stay in that area for many tourists. In addition to Toledo (my favorite, and I think you could spend more than one full day there), I especially liked Segovia and Cuenca. Cuenca is significantly faster by AVE than by car, but AVE tickets are pricey if not purchased well in advance.

I agree - not much to see/do on the coast at that time of year. The Atlantic (Algarve) will probably be icy cold and the Med won't be warm enough for swimming either.

Jean, there is nothing wrong if your idea of a great holiday is extended time in a condo on the coast. However, if validation of that style of travelling is what you are seeking from this Forum, then you may not find it forthcoming.
Everyone is different, and Spain has so much variety to offer.

First, we can sleep on the plane and can't get into anywhere until 4p.m. so arriving early morning gives us lots of time with a stop for lunch to get there. Prime objective to stay in Condo's is that we save money by renting a two bedroom 2 bath & make our own breakfast & some dinners; we have two great people that like to cook! Some condo's are cheaper by the week.
I'm not sure exactly what where we'd like to lite for a week at a time; we love history so that's why we thought a week in Porto would be nice, may extend Lisbon and only stay in the Algarve for 4 - 5 days then stay longer in the Malaga area where we can do day trips i.e. Seville, Alahambra, Granada etc. while relaxing a few days in between. Changing from March to April so the weather will be nicer?
As I've said, we keep changing our itinerary on others suggestions. We are in a small town and the library is not expansive on travel but have checked online; I do value other travelers opinions that have experienced these two countries.
New:
Madrid – Porto -5 ½ Hrs.
7 Nights Porto

Porto – Lisbon -3 Hrs.
4 Nights Lisbon

Lisbon- Quarteira 2 ½ Hrs.
5 Nights Quarteira
Quarteira – Malaga – 4 ½ Hrs
12 Nights Malaga
Malaga – Madrid 6 Hrs.
3 Nights Madrid
These are all subject to changes "again" lol... just want to finalize so as soon as the airfare sales come up we can book air & hotels/condos; which probably won't be until the end of May now that we've moved our trip to April instead of March.
Jean

Check amazon.com for guidebooks. You may well be able to pick up a couple of books a few years old for under $10. You should get current editions before your trip, but for now you need something to help you decide where to go. That needs to be pinned down before you buy your airline tickets. It's very dicey to plan a trip like this without reference material. It's not like you're just spending a week in Madrid. If this is your first trip to Europe, you'd also benefit from reading Europe Through the Back Door. (And if it's your first trip, I will gently suggest that you may be far too optimistic about how much sleep you're going to get on the plane and how safe a driver you will be immediately afterward.)

I understand the financial advantage of a condo for a group such as yours, but I suggest doing some checking on driving times. ViaMichelin, generally thought to be optimistic, estimates Malaga to Seville at 2 hr. 41 min. one-way. Seville is a rather large city where many tourists spend multiple days. I wouldn't be satisfied doing it as a day-trip from Malaga, and a 5.5-hour roundtrip is not one I'd want to do twice.

Cordoba, another top sight in that area, is estimated at 2 hr. 7 min., so a bit more doable. You might also consider the smaller Ronda as a possibility (2 hr.). I'm not sure how well Granada will work (est. at 1 hr. 48 min.) since the Alhambra is such a time-consuming sight. I'm also not sure about driving conditions in (and in and out of) Malaga in general.

To me, your preference for driving is a bit of a complication. The logical places for long stays on a first trip are often the major cities, because they're chock-full of sights. And there are often quick trips to be made by train or bus to top surrounding spots (like Toledo from Madrid, or Sintra from Lisbon). But navigating in and out of a big city via car can be stressful, and parking can be complicated and costly. Traveling by car to some destinations can take far longer than by train, though of course the car will be very handy for visiting smaller towns. If you didn't have plans for a car, I'd be urging an extended stay in Madrid because it has so many fabulous side-trip possibilities by train.

One thing to remember is that, for the safety of your possessions when you're in transit from one hotel to another and stop for lunch, you need a car with a trunk large enough to store all of your luggage out of sight. There are cars large enough for four people that do not have trunks large enough for four people's luggage.

We've been to Europe many times, mainly on drive yourself tours. For some reason Spain & Portugal is giving me stress. I've read many books, websites and thought the Med. would be a nice long stay but most here say it's boring so I keep changing our itinerary!
So I guess we'll stay in other cities a shorter time; it will cost more but looks more interesting???
Arrive Madrid – Salamanca – 3 Hrs.
1 Night Salamanca
Salamanca -Porto - 3 Hrs.
5 Nights Porto

Porto – Lisbon -3 Hrs.
4 Nights Lisbon

Lisbon Quarteira 2 ½ Hrs.
5 Nights Quarteira

Quarteira – Seville – 2 ½ Hrs.
2 Night Seville
Seville – Malaga – 2 Hrs.
9 Nights Malaga – Day Tours to Granada, Ronda, Nerji etc.
Malaga – Toledo – 3 ½ Hrs.
2 Nights Toledo
Toledo - Madrid 1 Hr.
3 Nights Madrid
Jean

Rhonda is an amazing place. Cave paintings in Altamira, Caves in Nerja, Moorish architecture in Cordoba

I don't know where you are getting driving times. I just looked at viamichelin.com for Sevilla-Malaga. It says 2.75 hours and that's optimal conditions, without any stops, presuming you are a maximum speed and don't make any wrong turns or get stuck behind a slow-moving vehicle, etc etc. It doesn't take into account the time to find a parking place or an address. Malaga to Ronda is 2 hours, Granada is nearly that, both with the same caveats.

If you spend 3-4 nights in Ronda, you can explore the hills and pueblos blancos easily. But if you want to do that from Malaga, that will add another couple hours or more to get there and back.

According to Google Maps, Seville-Malaga is 2 1/4 Hrs. We'll have lots of time...
J

Let us know how that works out for you. Most of us don't rely on Google, but if it's more accurate, we'd all like to know.

I've used Google for years in North America & Europe; when I set up the addresses in my GPS it matches Google..

J