Portugal / Spain/ Gibraltar / Tangier

What have you identified that you want to see so far? I think you'll get much more help here if you develop a rough sketch on your own.

With only a few exceptions, people who've been to Morocco are going to urge you to skip Tangier. Although 24 days sounds like a lot, it's not even a lot of time for Spain alone. Rather than recommending you go to a better Moroccan destination (like Marrakesh or Fes), I suggest you leave Morocco for a later trip. I know it looks convenient because of its proximity to southern Spain, but it will not be so convenient when you starting investigating the logistics. The ferries do not depart from places most travelers want to visit, for one thing. Fortunately, there are flights from a number of European cities to Marrakesh and Fes (as well as Casablanca, but that's a modern city and not where you should go, either). It will not be difficult to incorporate Morocco into a later trip to another part of Europe when you can give it more time.

I cannot comment on Gibraltar. I've never been there because it has never sounded interesting enough to me to justify the time taken from other places--and I've spent about 4-1/2 months in Spain since 2017. Do some research on the sights in the other places you decide to visit, then consider how much time it will take you to add the detour to Gibraltar.

It's harder than you might imagine to combine Spain and Portugal on one trip unless you do a loop by car. That's because there just aren't very many public-transportation links between the two countries. The ones that exist run infrequently, so keep this potential monkey wrench in the back of your mind as you identify possible destinations and then trim the list. The border-crossing options I'm aware of are buses from Seville to the Algarve (where I'd spend none of my time on a trip such as yours), an overnight train between Lisbon and Madrid, probably some buses across the border near Badajoz (not sure), and buses and/or trains from northern Portugal up to Galicia (though linking Porto and Santiago de Compostela may involved awkward layovers). You can check skyscanner.com for flights.

In terms of architecture, I think the most distinctive places in Spain are Barcelona (modernista), Toledo (medieval), and Seville/Cordoba/Granada (Moorish/mudejar). There are many other great destinations, but if you have only 24 days and are going to try to include Portugal, you won't have time for a lot more. Of the Spanish cities I've mentioned only Barcelona is on the coast. There are other nice coastal destinations (Cadiz, Malaga, and some cute little towns in the south; Valencia on the east coast; and places in the Basque Country and Galicia along the north and west coasts), but I'd rank them behind the five I mentioned first.

I've spent less time in Portugal, but one obvious destination is Lisbon (some Manueline architecture).

How much time in each place will depend on the breadth of you interests. More than one day can be spent in Barcelona tracking down modernista buildings even without going inside any of them. Then there are the museums. Of the other four, Seville is the largest and probably needs the most time.

Potential side-trips would also factor in the time to be spent at a stop. Many people side-trip to Sintra (palaces) from Lisbon. Many people like to stay in Madrid (especially art lovers) and take day-trips to Toledo, Segovia, Salamanca and/or Cuenca. I don't like to rush and opted to spend multiple nights in each of those smaller places.

That’s a lot to do in 24 days but I’m no stranger to trying to cram a lot in a small amount of time. I have a rough idea (without having gone myself OR knowing what really interests you) of what I would do...or at least a draft for other people to weigh in on. Again, this is just a rough idea based on lots research I’ve done in the past for the region. Also I added one more night than days in each destination to account for travel time. The more destinations, the more travel days you’ll need, the more time lost ultimately ...so just keep that in mind.

In no particular order geographically...
1. Barelona : 3 days 4 nights
2. Madrid : 3 days 4 nights
3. Seville : 3 days 4 night (I would also take at least a day trip to Granada, you can mix and match the days if two full days in Seville isn’t enough for you)
4. Lisbon : 3 days 4 nights
5. Porto??? : 3 days 4 nights (idk a lot about Porto but supposedly it’s the other destination in Portugal you should see after Lisbon so I just included it.)

That’s 5 cities and 20 days. Idk a lot about Gibraltar or Tangier. I can’t imagine you need a lot of time at either but this comes from a place of ignorance. That leaves you with 1 day, 2 nights for each, which seems...slim. So play with the days and mix and match them to keep it within 24 days. It’s a big wish list for 24 days so I just have a rough idea of what I might like to do, so I named the 5 most significant cities I could (Porto so it wasn’t just Spain + Lisbon.)

1. Skip Tangier, I have been to Morocco and there are wonderful places in that country but Tangier is not one of them. Rabat, Fes, Marrakesh and Agadar are nice, but for 24 days, you should stick to Iberia first.
2. Spain, my favorite cites there are Seville, Toledo, Granada, Barcelona, Segovia and Salamanca. Madrid is nice mainly for the Prado and being close to Segovia and Toledo. Stay in Madrid for 4 days and spend two on day trips to Toledo and Segovia. Seville deserves 3-4 days. Granada and Barcelona are on the eastern part of the country, but the Alhambra is worth spending a full day there and Barcelona 3-4 days.
   3, Portugal, Lisbon of course for 3-4 days, then Sintra on your way to Portugal, Obidos, with its Roman walled town. Cascais is a nice coastal town worth a day. Bathila Cathedral on your way to Porto. Three days in Porto, with another day to explore the Douro River valley. Salamanca, Spain is close to the Portuguese Border from the river valley.

Hi Demetrius,

Sounds like your focus is similar to ours. We were in Spain for 21 days and didn’t have time to cover Portugal or the extra time to try to add Gibraltar & beyond to that trip. I will attach a link of my trip report to give you an idea of timing. If you wanted to add Gibraltar and Tangier, it would fit with your extra few days in our itinerary after Malaga. And I have heard from others that Tangier is similar to visiting Mexico by going to Tijuana - best to pick a better town and spend the extra time.

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

You can fly nonstop from New York, Boston and Miami to Barcelona and from Lisbon to Miami, Boston, Chicago, New York, San Francisco and Washington DC. If you can fly into one city and out another, you'll have more time. As the others have suggested, I would focus on Spain and Portugal and cut out Gibraltar and Tangier. Not that I wouldn’t go to Morocco, but not Tangier's.
In Spain I would focus on Barcelona and a day-trip to Figueres to see Dali’s museum. From Barcelona I would take a direct (no connection required) overnight train to Granada and sleep in a couchette, that’s how I got there. From Granada I would take a direct train to Sevilla and the same to Madrid. In Madrid, I would take day trips to the places that the others have recommended that are nearby, especially Toledo. You can fly nonstop from Madrid to Lisbon for less than $50, however, you’ll have to pay to check your bag(s).
My least favorite place on this itinerary was Sevilla. I don’t understand all the hype that it gets, but I love Barcelona, Granada and Lisbon. What I liked about Madrid was the art and its close access to Toledo.
Gibraltar is expensive and there’s no cheap place to sleep. Most people don’t like Tangier's either since it’s a tourist zone.

Although there are very good, fast trains on these routes, there are no non-stop trains from Barcelona to Granada, Granada to Seville, or Seville to Madrid.

Things might change before the trip happens, but at the moment the only nighttime departure I see from Barcelona with connections to Granada takes almost 16 hours and involves two changes of train, one of them with an 8-hour layover (all night long) in Madrid. So that's not a night train in the usual sense of the word and would be an unbelievably miserable experience. There's a departure around 8:30 AM that takes a bit less than 6-1/2 hours; it has seven stops but requires no changes. Many people would opt to fly instead.

Your proposed destinations cover a HUGE geographic area, essentially the size of Alaska, offering a plethora of menu options. Let's consider crafting a journey offering the maximum potential of creating wonderful memories of travel experiences.
Cruelly I shall dump Gibraltar (it's a rock) and jumping across into Tangier (simply to reduce travel stress). Consider that if you spend time in Barcelona, Madrid and Andalucia you will have visited three diverse cultures whose geography, architecture and history offer completely different experiences. You could spend base for a week in each of these locations and mix in day trips to enhance your experiences. Public transport is excellent with subway connections to trains offering an almost seamless mode of easy convenient travel. Andalucia creates the need to split your time between several locales, most commonly defined by stops in Seville and Granada. I propose spending 17/18 days in Spain and then 7/6 days in Portugal, a country offering another totally different cultural experience separate from what you will find in Spain.
Important to know the months you plan to travel, our favorite time is early October and have also been in May.
Be well!

Holy Week (Semana Santa) brings major crowds to Andalucia. That's something one should be aware of and either take advantage of or avoid. Semana Santa pushes lodging rates up a lot and slows down sightseeing because of reduced hours and crowds in the streets (in some cities on some days). Mid- to late-spring weather can be very nice in that part of Spain. Summer is likely to be a punishing experience there.

We had a somewhat similar trip planned back in June 2002, and as mentioned above, Spain itself is so big that we decided to focus on the southern half. We also planned to visit Gibraltar, and to make the trip across the water to Morocco, maybe taking an additional couple of days there to see more than just Tangier. As Rick Steves has always said, “A day in Tangier is more interesting than spending another day in Spain.” However, as we were planning that trip in the fall of 2001, the 9/11 attacks had just happened, and I got the chance to ask Rick himself at a presentation he was making in Denver about going to Morocco. He suggested at the time that he’d avoid Morocco and Tangier. So we added a week to Portugal instead, to the 2 weeks in southern Spain that trip. We finally made it to Morocco for 3 weeks in January 2019, but still not to Tangier. And Gibraltar got dropped from our plans, but if this is your one time to see Tangier (and even Morocco), and if you’re already going to be in Gibraltar, then you’ll be in a position to make that all happen.

Although you’re planning on train travel, we did have a rental car, for much of southern Spain and for Portugal. We actually flew from Granada, Spain to Lisbon, and rented a car there. We didn’t take any time for beaches or clubs. Two weeks in Spain, including Madrid, Segovia, Toledo, Granada, more of Andalucia, including hill towns and caves with prehistoric paintings, plus Ronda, and Seville - that gives you about a week and a half left to fit in Granada, Tangier, and Portugal. In addition to Lisbon and Sintra, don’t miss Evora.

What about Rick Steves tours? He offers an 11 day “My Way” version for Spain, where you do your own thing for sights, with lodging and transportation provided by the tour itinerary.

Then there’s a full group version for a 12 day Heart of Portugal tour. At least check out the itineraries on his Website for destination and timing ideas.

Gibraltar doesn't get enough travel love. There are so many great things to do there. I haven't been for many years but I loved my time there (just one day):

• take the cable car up the rock to see the Barbary apes
• St Michael's Cave is probably the best accessible cave visit there is in the world
• if you're into naval history as I am, the Trafalgar Cemetery was nice
• if you're into WW2 history, there are caves and bunkers that Eisenhower used to direct the invasion of North Africa
• I found just walking the warren of narrow streets in the downtown to be fascinating.

I loved Gibraltar and hope to go back some day (like you, combining with Tangier -- I don't care what the naysayers say).

I loved Gibraltar and hope to go back some day (like you, combining with Tangier -- I don't care what the naysayers say).

Which is fine but if people ask for advice about somewhere then the acceptance is that they are intending to act upon the advice otherwise why else ask?

I'm glad you love Gibraltar. It has its interesting sights and is slightly quirky however it's not somewhere that I would go out of my way to visit. As a Brit it comes across as a bit like Swindon in the 80's but with better weather and some thieving, sometimes vicious, apes thrown in. The Rock is the most interesting part of the territory and the wartime tunnels will appeal to military buffs particularly but in terms of culture it's pretty naff.

One piece of advice I always offer is not to drive into Gibraltar. The Spanish are still quite tetchy about Gibraltar and often make things difficult at the border. Consequently the queues to drive across the border are usually long so it's far easier to park close by on the Spanish side (there are a number of underground parking lots) and cross the border on foot which is far, far easier and quicker.

As for Tangier, it really offers nothing of any appeal. It's simply a run down, dirty port city completely devoid of charm or interest. It may well be in Africa, it may be tempting to make the short trip across the sea (bear in mind that sailings are frequently cancelled due to the frequent strong winds across the Straits) and if you're interested in riding mistreated camels on the beach or watch snakes being taunted then there's ample opportunity to indulge in such cruelty but other than that expect to be viewed as someone there to be ripped off.

Sorry, I meant to say direct meaning you don’t have to connect.