Itinerary Advice - Southern Spain

Let's say that you leave Ronda on the 9:00 train and get to Tarifa around noon (with a bus connection at Algeciras). That doesn't leave enough time to roundtrip that day to Tangier, but of course, you could sleep in Tangier instead of Tarifa. On the travel day to Granada, if returning from Morocco, you'd have to be on a train at Algeciras by 15:30 at the latest (I did not check the bus schedule). It all becomes a bit more confusing when you add in the time change between the two countries and the possibility of boats running late. So you need two nights (not one) in either Tangier or Tarifa.

I would also rather see two nights in Granada. However much time you have, remember that you need to reserve ahead for entrance to the Alhambra and should give that site a few hours. If you decide to fly from Sevilla instead, you could head from Toledo to Granada earlier in the trip, reversing most of the order.

I would think if you have ten nights to play with then make them all 2 night stays - Granada definitely needs 2 nights. Personally I don't see the value of a 'day trip to Tangiers' and would look at Cordoba instead.

We land in Madrid,
2 nights in Toledo,
2 nights in Sevilla,
2 nights in Ronda,
2 nights in Tarifa with a day-trip to Tangiers,
2 nights in Granada,
Flight out of Malaga.

Good ideas, thank you both!

I had another thought... is Toledo worth the visit if we have already been to many medieval hill towns in the past several years? Some in Italy, France, Bethlehem (basically a medieval hill town), etc.? Will it feel much different?
Should we skip that and go straight to Seville or Granada?

I think it's unproductive to make comparisons like that.
"It's just like 'such and such' so maybe I shouldn't bother".
Toledo is Toledo. Do your research to see if it appeals and then make your decision.

Toledo is filled with incredible history and culture. There are Roman elements, Visigoth features, Moorish architecture, Jewish synagogues, Catholic Reconquista sites and Spanish Civil War sites. Not many places with that much history overlapping. You need to get off the daytrippers path to see most of it, but it is well worth it if you enjoy history.

Funny, I've never thought of Bethlehem as a medieval hill town. Anyway, back to Spain. Will you rent a car or rely on trains and buses? Is Tarifa/Tangiers a high priority? Especially if you don't have a car, that's going to use a lot of travel time (and you'll have your luggage in tow all the time), then you aren't seeing Morocco, you're just seeing what is essentially a border town (somewhat akin to visiting Juarez or Tijuana and saying you've been to Mexico).

Every town I've visited in Spain has had its own character. My favorites are Cordoba and Toledo, partly because they both suit my slow-travel, absorb-the-atmosphere style.

To determine how much time you'll really have in each location, look at the train schedules to see the the departure and journey times. Add to that the time you need to pack/unpack, check in/out, get to/from train/bus stations, add a little for traffic, orientation, etc. If you plan to rent a car, use viamichelin.com to estimate driving times but take into account that they are optimal, no traffic, no wrong turns, no parking or rest stop or photo stops included. As a general rule, you use up 1/2 day in travel every time you change locations. So on a 1-night stay you leave yourselves with only 2 half-days to enjoy the place.

Chani, thank you for your reply and thoughts. Really helpful.

My wife and I decided that Tarifa and Tangiers will be skipped and we want to focus on the other towns.
Right now we are considering 1 night in Toledo, 4 nights in Sevilla (first day arriving late) with a day-trip to Cordoba, 2 nights in Ronda, 2 nights in Granada and then flying out of Malaga.

This should be a pretty solid trip.

Thanks for everyone's help!

Hola de nuevo (hi again), Kevin. You wrote 1 night in Toledo, 4 nights in Sevilla (first day arriving late) with a day-trip to Cordoba, 2 nights in Ronda, 2 nights in Granada and then flying out of Malaga

There are storage lockers in the Madrid train station not at all near the Toledo train, but close to the high-speed trains. You could make it a bit easier if you leave most of your luggage when you arrive and pick it up the next day. I always check luggage and take everything I need for the first 48 hours in my carry-on (my second biggest flying fear is that I won't see my suitcase at the other end - first is missing the flight). That would make it pretty easy. Even if you only have carry-on, it may make the Toledo stop a bit easier.

Much as I love Cordoba in the evenings, I see the wisdom of visiting as a day trip from Sevilla. Do take an early train so you can get to the Mezquita early. La Casa de Flamenco is a good place to see a performance - more serious than the touristy shows with drinks and food. Sevilla has the best tapas in Spain, hence in the world. Never met a Spanish wine I didn't like . . . though I'm not partial to sherry (shhh, don't tell Brad). Another possible day trip is to Jerez for a horse show on Tuesday or Thursday. It's about an hour by train from Sevilla. While you're there, take the Tio Pepe sherry tour, fun and interesting.

Are you going to use the train/bus from Sevilla to Ronda to Granada or rent a car? Once in Granada, consider doing the Nasrid Palaces evening visit on your first night, then going back during the day to see them again along with the rest of the sight. They look very different at night.