14 days trip itinerary Southern Spain and Portugal

This sounds simple but is not.

What cities are practical flight destinations for you? Have you checked airfares? This year I opted to fly into Madrid for a trip beginning in Andalucia because flights to Seville and Malaga were about $500 more expensive.

Do you plan to drive or use public transportation?

Picking up a car in one country and dropping it off in another usually generates a very high supplemental charge. Doing a loop trip means extra miles (time and money).

Public transportation comes with its own challenges, because ground-transportation links between the two countries are shockingly limited.

I have never been to Evora (Portugal), but I went to the Algarve when it was considerably less over-touristed than it is today. To my mind that area is not the most interesting part of Portugal and can't hold a candle to such Spanish classics as Seville, Cordoba and Granada. If I had two weeks I would spend all the time in either Spain or Portugal, and I would skip the Algarve.

Seville, Cordoba and Granada are now connected to each other and to Madrid by fast AVE trains, so it would be possible to visit them by train (much faster than driving) and rent a car for a few days to see some smaller towns. I'd want a minimum of 4 nights in Seville, 3 in Granada and 2 in Cordoba. My own itinerary had an extra night in each city, in some cases to allow for a day-trip.

Other places of interest in southern Spain include Ronda, a number of small white towns (Arcos de la Frontera, Grazalema, Zahara de la Sierra, Vejer de la Frontera), Malaga, Cadiz and Jerez. In northern Andalucia you have Ubeda and Baeza.

You need to get a comprehensive guidebook for southern Spain and another for Portugal to figure out what interests you. Everyone's taste is different. It's important to figure out the basic extent of your trip before you buy airline tickets.

We visited northern Spain in October 2015, including Madrid and points north and east, with frequent rain, and you may already know this, but Oct. 12 is Spain’s national holiday.

Are you planning to rent a car for some of your trip? On a much earlier trip one summer, we visited southern Spain and Portugal. Rick Steves’ guidebook back in 2002 combined both countries in one book, and we started for a week staying at a timeshare trade (wouldn’t do that again) which required long driving days to visit points northwest of Malaga, including Ronda and the Cueva de Pileta. We moved on by train to Granada, easily worth 3 nights. Tour the Alhambra, and get a soak and a massage at the Arab hammam baths in Granada.

We then took a cheap Vueling Air flight to Lisbon, for 3 nights, using walking and public transportation to visit the upper and lower parts of Lisbon, plus Belem. See a fado music performance, with dinner.

We rented another car, driving to Sintra, up to Obidos (1 night) and then to the magical, historic Evora (2 nights), although an extra night in each would’ve been better. Dinner at the historic, elegant Pousada in Evora was a special evening. Visiting our first Neolithic dolmen, before seeing them in other, more Celtic places elsewhere in Europe, was a surprise, as was the drive through cork tree forests.

We kept the Lisbon car to drive back to Spain, paying a fee to drop it off in a different country, and stayed in Seville (flamenco dancing and music capital of the world) for 2 nights, then on to Arcos de la Frontera (2 nights). A nationwide strike shut things down, and prevented a visit to the Sherry producers in Jerez.

It’s been a long time, so I don't immediately recall every place we visited, and exactly where we stayed and for how many nights. In retrospect, flying into one city and out of another could’ve saved time and money, but we started and ended in Spain, with a bit of Portugal in the middle. Hope this helps, if even a little.

Hello from Wisconsin,
Two points.

One, Andalucia is known for being the warmest (hottest) location in Europe. Year round. So northern cold-country touristhave been coming here forever. March was lovely for touristing, but have you checked typical summer time temps, and have you looked currently? The north coast of Spain is typically cooler. Wetter and cooler, it looks like Ireland on steriods.

Two, off the beaten track. Not easily done in Andalucia. Anchored by three great cities (Cordoba, Granada, and Seviila) you must work hard to find hidden corners. Ronda and other 'white cities' are over run with Spaniards who have built houses and condos not to mention day tripping non-Spanish tourists. Being villages in the mountains there is limited space to accomodate all who want to be there. The countryside outside of the olive orchards is beautiful. The coast line is filled with tourists there for two days to drink and soak up the sun made affordable by cheap airlines. I will not milign the Limeys by calling them out. Baeza and Ubeda might classify as lightly traveled off the heavily beaten track. (Baeza has a must visit bar called Cafe Theatro Central). Once again, the north coast of Spain is filled with many off the beaten track opportunities.

Check the temperatures, and if a place is in Rick's book or Fodors, it probably has plenty of tourists.

Two votes for the north coast.

Wayne iNWI

I think Southern Spain shouldn't be impossibly hot in October, but in truth I have not researched fall weather conditions. That can be done on timeanddate.com, which has actual, day-by-day, weather stats going back at least 10 years.

I like northern Spain a lot, but I think of it as a great place to escape the miserable heat of summertime Spain. It tends to be overcast and rainy even then.

If you truly want to avoid seeing many other foreign tourists in southern Spain, you can go to places like Ubeda, Baeza, Carmona and Priego de Cordoba. However, in my experience most areas of the larger cities don't see all that many foreigners, because the latter tend to make brief visits and go to the same few sights.

I think October is the perfect time to visit southern Spain. We were there in mid-September through October 3 in 2017. We had 80's while in Madrid, Toledo, Cordoba, and Granada. It was in the 70's in Malaga, and 90 - 95 in Seville in very early October. So Seville could be one of your later stops so you are there mid to late October.

I recommend reading some good guidebooks, such as Michelin Green Guide, Lonely Planet, Rick Steves, and perhaps Rough Guides.

Are you considering Madrid and Toledo? If you decide to visit only Spain on this trip, this was our itinerary, which you could use as a guideline:
Madrid - 4 nights; Toledo - 1 night; Cordoba - 2 nights; Granada - 2 nights; Malaga - 2 nights, and Seville - 4 nights.
Don't know if you are considering Malaga, but we loved it, and thought it was nice to have some coastal ambience, even though we didn't go swimming. There is a lot to see and do in Malaga, and I think it's an under-rated city. BTW, I think 2 nights each for Cordoba and Granada are the minimum number of nights I would recommend, and 4 nights in Seville is the minimum number of nights.

If you don't want to visit Madrid and Toledo, you have time to visit the white towns and/or Ubeda and Baeza that others recommend. I haven't been to those yet.

If you really want to see Portugal on this trip, I recommend flying open-jaw or multi-city. For example, fly into Madrid and fly home from Lisbon. If you don't want to visit Madrid, then take the train to Cordoba as soon as you land. Organize your itinerary so that Seville is your last stop in Spain, and then you can fly from Seville to Lisbon via TAP. Spend 5 nights in Lisbon, which could include a day trip to Sintra. I haven't been to other parts of Portugal yet, so cannot comment on other places in Portugal.

If this was my trip, I would probably visit Spain only, and leave Portugal for another time. But if you don't think you will return to the Iberian Peninsula any time soon, then at least visit Lisbon, a wonderful city.

We went to Spain in Sept/Oct in 2017 and had a wonderful time! Here's my Trip Report - might help with your itinerary:

https://community.ricksteves.com/travel-forum/trip-reports/1st-time-to-spain-trip-report

There's lots of great advice in the posts above, but I just want to emphasize a few of acraven's points.

Although we in the US think of Spain and Portugal as practically one country, connections between them are surprisingly skimpy, and combining the two of them in a single trip is surprisingly complicated. There are a very few trains, often at odd hours; there are a few buses, often requiring connections even between major cities not that far apart; and there are flights (more than you would think, due to the lack of other options). You can rent a car, but a car rented in one country and dropped in the other will have a high surcharge (reported here as several hundred euros).

Do decide on an itinerary BEFORE you book flights, although acraven's point about some flights being much more expensive also comes into play. And do look at transit options before you finalize an itinerary, to make sure it's doable (someone posted that they were going to take a train from Seville to Lisbon, which is not possible because trains connect only part of the route between the two cities).

Iberia has multiple airports; depending on where you're flying from, it may be easy or hard to reach some secondary cities. It also may or may not cost more. A common mistake is that people book round trip to Madrid, then (for instance) decide they want to focus on Barcelona and Andalucia and not see Madrid. They then have to use a day, and some extra money, each getting between Madrid and the places they want to see. In this scenario, a flight that only "saves" $100 over a flight into Barcelona and out of Seville isn't worth it. A $500 saving, on the other hand, might be - even for me (I'm very averse to flying where I don't want to be, but on the other hand, coming from New York I have many more options than most people do).

Portugal has three airports (Lisbon in the center, Porto in the north, and Faro in the south). Spain has many airports. If you're looking to fly to Andalucia, note that Malaga airport is much larger, and has many more options, than Seville airport, while Granada airport is very small with very limited flights.

I've no idea what flights are available to you, but if you've got to change aeroplanes anyway to get to/from southern Spain it may not make much difference if you make the change in another European country's hub airport with flights to the regional Spanish airports.

There are plenty of "off the beaten path" places in southern Spain if that is code for "not many other Americans". But it's harder to find places without British or north European tourists - perhaps because they're more adventurous, or possibly just because they get more holidays and it's cheaper & easier to get to Spain of course. Within Andalucia, neither the provinces of Almeria nor Jaen (except sometimes Ubeda/Baeza) seem to be mentioned much here and any mention of Granada province seems mainly to be limited to Granada city itself. So there are options aplenty if that's what you really want.

On the other hand, if this is a first visit and with limited time, in terms of cities I'm not sure I'd skip Sevilla to see Jaen. And, there is a simple reason Cordoba gets more mention than Almeria - it's better.

If you flew into Lisbon for 4 nights, including Sintra, then train (or coach?), to Porto for 2 nights, then fly (limited departures, so need to arrange flight day to fit), to Sevilla for 5 nights, with a day-trips to Carmona and Cadiz, then train to Cordoba for 2 nights and fast train to either Madrid or Malaga to fly home. Whilst none of these cities are off the beaten path, they do have interesting parts that are. So with stops of 2 or more nights you have time to explore the less visited parts as well as the major tourist sights.

Weather in October in southern Spain should be delightful - sunny, mild and only intermittent rain. I imagine Lisboa/Porto is nice too, perhaps a little cooler, but not cold.

PS On music in southern Spain (esp. Sevilla), you'll come across a lot of flamenco. It is god-awful, although not quite as bad as the fado you'll get in Portugal (esp. Lisbon). Still, if you want traditional "music" then it's there.