Gibralter—Worth it?

If you’re in the area it’s worth a quick stop, but I wouldn’t go out of my way to visit. The siege and WWII tunnels might be worth seeing if you like that sort of thing. When I lived in Spain in the late 70s, the border with Gibraltar was closed, so on a number of occasions I stood on the Spanish side of the border and was only able to look across it at the rock. Took my children there in the 90s and was happy to be able to cross the runway and go up the rock. Now that I did that, I have no desire to return. Since you intend on being in Tarifa, Gibraltar is only about 20 miles away.

If you intend on driving, once you have a pretty good idea of your itinerary, research some of the smaller towns along your route. Some may have sights you’d be interested in seeing, or May simply be interesting enough to walk around or stop for lunch. You get a better view of the countryside from the smaller roads, but it will take longer to get to your destination.

I wouldn’t bother with Gibraltar as there are more interesting places to see in Spain.

Grenada in the West Indies doesn’t fit well with your trip, but Granada is worth a couple of days. Tickets to the Alhambra sell out months in advance. It can be cold here in winter.

I liked Jerez for a few days - sherry and horses. I covered Cadiz as a day trip from here.

I also wouldn’t bother with Tangiers.

Jennifer-

I'm blaming auto-correct on that typo, regardless of whose fault it actually was! :)

Anything to recommend Jerez if I have little interest in horses and none in sherry?

Why not Tangier? (With the understanding that one must divert from a well-worn tourist path.)

(This was actually the first result when I thought of it last night and googled 'tangier day trip spain': https://www.ricksteves.com/watch-read-listen/read/articles/tarifa-spains-southernmost-port)

I have heard Tangier is comparable to Tijuana. Wouldn’t be my cup of tea. Cordoba, otoh, is pretty wonderful, brimming with history. There is plenty of evidence left of the pre-1492 Jewish and Moorish life. The Mezqita is a wonder, and the rest of the medieval center is beautifully maintained. Close by is the archaelogical site, Madinat al zaharah (sp?), the summer palace of of one of the rulers of el Andalus. The excavations were at an early stage when we were there 20 years ago, but I’ve read that the restorations have progressed greatly since then.

The only thing I can think of in Jerez de la Frontera, other than horses and sherry, is its Alcazar. It’s worth an hour or so visit. Cadiz is about a 30 minutes drive from Jerez as is Arcos de la Frontera, one of the white towns with a picturesque overlook. Also nearby, in Puerto de Santa Maria, is the small San Marcos castle where (supposedly) Queen Isabela gave Columbus the money for one of his voyages. That trip departed Spain near San Lucar de la Barrameda. While I haven’t been to it, 36 miles from Jerez is El Rocio that is supposedly like an old Wild West town.

Finally, if you didn’t want to drive to Cadiz, there’s a ferry you can take to Cadiz from either Puerto de Santa Maria or Rota.

Morocco is wonderful. Tangier is just not a good example of Morocco. I know it looks so close, but as you've already discovered, it involves a good bit of traveling just to get to the port on the Spanish side of the Straits. You'll chew up major portions of at least 2 days in order to have a few hours in a mediocre port town. Andalusia is worth your entire 2 weeks if not longer. I consider Cordoba essential, and Malaga was more attractive and interesting than I expected it to be. Ubeda and Baeza in the northern part of the region are also worthwhile, though they are geographically more challenging and I don't know what the November weather is like.

You may not be aware that a lot of European cities have non-stop flights to far better Moroccan destinations than Tangier, including Fes and Marrakech. I'm not suggesting you fly to Morocco to see those cities on this trip; you have plenty to see in southern Spain. But Morocco can be added to a future trip to France, Germany, England, etc. This isn't your only chance--or even your best chance--to see it.

Thanks for all these insights, everyone!

I should have mentioned that the only reason Cordoba isn't on my list is that it's the only thing I remember well—and fondly— from my prior trip to Andalucia 20 years ago. It would certainly be a "must-see" if I hadn't already.

Gibraltar is an interesting little colony and the various military sights are a nice contrast to towns back in Spain. It is certainly worth a day trip if in the area. However, I would not make a long journey just to visit, especially as you already have a a rather full itinerary for two weeks. If you stick to Tarifa/Tangier then you pass Gib. on the way too/from either Ronda or Granada so you could call in for a day. Supposedly the border controls are going, but I'd still park in Spain (La Linea), and walk across rather than trying to park on Gibraltar itself.

If you drop Morocco, then I'd also skip Tarifa. There is nothing wrong with the town, but nor is it especially interesting other than as a place to get a ferry. I think there is a castle but loads of places have castles.

If you aren't interested in horses, then Cadiz is a better choice than Jerez. Indeed, Cadiz is better anyway, with a more atmospheric setting and some diverting Roman and more recent sights.

If you decide to include Tangier you can easily drive to Gibraltar from Tarifa since it's close. Have you considered spending your 2 nights in Tangier? The ferry crossing is fun and not too long. On our trip we flew to Marrakesh and then took the train to Tangier before catching the ferry to Tarifa. We then took the bus to Algeciras and then the train up to Ronda for a few nights (definitely worth visiting).