ten days in Spain ending in Gibraltar

I suggest getting some ideas at https://www.ricksteves.com/europe/spain and buying Rick's latest guidebook, which is linked there. Most tourist destinations are served by train and others by bus, so you're unlikely to need a car. Or you might get a car just for the southern portion of the trip. Gibraltar is served by bus, about half an hour from Algeciras (bus station near the train station) to La Linea-Gibraltar stop.

Our local library also has RS's Spain book 2018 and 2016 editions which include extensive recommendations about Gibraltar. Yours might too, Brian. It is a great resource!

If you're considering hotel accommodations in Gibraltar, avoid the O'Callaghan Elliot hotel. It is under construction until at least the end of next summer. We were in Gibraltar last week & walked by that hotel to have a drink at the end of the day. Construction was going on so you couldn't even enjoy drinks outside as the jackhammer noises were unbearable. Our waiter said the earliest construction will be completed is next September.

Getting from Spain to Portugal can be a bit awkward if you aren't driving, and there is tons to do in each of those countries, so I'd stick with Spain on this trip. I'd give serious thought to sticking with Anadalucia on this trip because it has a good variety of sights and the best mid-winter weather. It's definitely an area most of us would avoid visiting in the summertime. Don't forget that the days will be quite short in February, so you won't have as much daylight sightseeing time as you would during a spring-summer-fall trip; give yourself enough time in the major cities and towns.

If you happen to be a big art fan, you should plan at least a few days up in Madrid. The AVE service between Seville and Madrid is very fast, and the tickets will be inexpensive if you are able to pin down your plans enough to buy promo tickets (unchangeable, non-refundable) shortly after your dates go on sale. The tickets, once purchased, will tie you to traveling at a specific date and time. There's also the potential for saving money on advance-purchased tickets within Andalucía, but I'd work on the timing to Madrid (if you decide to go there) first, because hotel rooms in Madrid can be pricey as your arrival date approaches.

For train fares and tickets (you may need to pay with PayPal), go to renfe.com. That website can be a bit awkward for some routes. If you run into difficulties and are just looking for schedules (not prices), you may prefer the Deutsche Bahn site.

Before someone brings it up: I wouldn't recommend a day-trip to Tangier, but if you wanted to peel off additional time (maybe 5 days?) to see places like Fez and Marrakesh, I'd say that was worthwhile. For that, or if you decide to go farther afield in Spain, I recommend looking for flights on skyscanner.com. But again, I think the amount of time you have is great just for Andalucía.

I'm a big fan of the trains, or buses when there's no train service; Spanish intercity buses are quite comfortable. But if you wish to see Ronda and the white villages like Arcos de la Frontera, you will be glad to have a car for a few days. Ronda is accessible via public transportation, but stringing together several of the smaller places would be difficult if not impossible via bus.

Everyone has his favorite destinations, but I think most of us would agree that Seville, Granada and Cordoba are the top three. If you need to, you can treat Cordoba as a day-trip from Seville, though I'm sure it's nice to be able to spend the night there. After the top 3, you'll find various proponents of Ronda, the white towns, Cadiz, Jerez, Malaga and Nerja. All of the places I've mentioned are rather touristy, though perhaps February won't be so crowded; if you think you'll need some time in more out-of-the-way spots, there's probably someone here who can make suggestions.

I think spending your time in Spain and saving Portugal for another trip makes the most sense. The two countries are not as easy to connect as they look, and given that you need to end in Gibraltar, focusing on Spain makes the most sense. Here's what I would do, with mostly 2-3 nights per city and 12 nights total before Gibraltar.

I'd fly into Madrid, spend 2 nights there (3 if you do a day trip to Toledo), then 1 night in Cordoba, 3 in Seville, 2 in Ronda, 3 in Granada, then to Gibraltar. Connecting these towns can be done by train/bus. You might want a car after Seville to drive the hill towns around Ronda, then return the car when you arrive in Granada. To be honest I am not fully sure how best to get to Gibraltar, perhaps you would need to change the order, ending in Seville before heading to Gibraltar.

A word about language - you will be fine with English, but I have noticed that Spain has many fewer English speakers than other countries in Europe. People are friendly and will try to communicate as best they can so you won't have trouble getting what you need...but don't expect to find a lot of people able to converse in English. Get a phrase book, learn a few words, and your few words of Spanish combined with their limited English will suffice.

Day
1. Fly to Madrid (4 nights)
2. Madrid
3. Day to Toledo
4. Madrid (or day to Segovia)
5. Train to Seville (3 nights)
6. Seville
7. Day to Cadiz / Jerez (or more Seville)
8. Train to Cordoba (2 nights)
9. Mezquita
10. Train to Granada (2 nights)
11. Alhambra
12. Train to Ronda (1 night)
13. Train to Algeciras & bus/taxi to Gibraltar

Two years ago we visited Spain and Gibraltar. We took the train to Algeciras. We took a taxi from the train station to Gibraltar. The taxi driver did not speak much or any English. But we had no problem indicating that we wanted to go to Gibraltar. The trip was about 30 minutes (give or take) and was not particularly expensive. At Gibraltar you have to walk across the border and then catch another taxi. No problem and of they speak English in Gibraltar.

Regarding English. Whenever we really needed to talk to someone in English, such as at the train station to buy tickets, there always someone who would say that he spoke “a little” English and it was more than enough. One time we were having trouble purchasing subway tickets and a passerby walked us thru the process by pantomime and we were on our way. The folks at the front desk of hotels always spoke English. At sidewalk cafes “tinto vino y cerveza, por favor” or “coke light, por favor” always got us what we wanted. In other words language was not a problem.

Thank you for all of the responses. They are really helpful.
I notice no one has suggested we go to Barcelona and I was wondering why that was?
A potential itinerary I am considering is:
FEB 3 & 4 - Barcelona,
FEB 5, 6 & 7 - Madrid,
FEB 8 & 9 Seville,
FEB 10 - Cordoba,
FEB 11 & 12 Granada,
FEB 13 - Algeciras,
FEB 14 - Gibraltar

I think you only have time for one city, either Barcelona or Madrid. Madrid makes more sense with your onward travel to Andalusia. Barcelona can be visited at any time and from anywhere, so I would leave it for a future trip.

I adore Barcelona. Spent 10 nights there last summer. It's not a place I'd recommend someone go for just a couple of days because there is so much to see and do there. A lot of the top sights pretty much require you to buy tickets in advance, because otherwise you'll spend a great deal of time in ticket lines. It's a problem if you're trying to see a bunch of the advance-purchase sites on a short visit, because how do you know how far apart to schedule those tickets?

Barcelona is wonderful, but you need to end in Gibraltar, which is at the opposite end of the country, and you said you wanted to spend 2-3 days per city. Barcelona takes more than that and is farther away. Might be better to spend your time seeing the highlights of the south, with a couple days in Madrid. I do find Barcelona more interesting than Madrid, but it also feels separate, culturally, from the other parts of Spain.

I suppose one could go to Barcelona for 4-5 nights, then to Seville for 3 then Cordoba for 1, then Ronda for 1-2 then Granada for 2-3.