Itinerary advice and Private driver suggestions in Spain

If you went to Sevilla first, and returned to Madrid for last, would that help?
Or, you could go to Cordoba first, then Granada, then work your way back, making use of drivers for Ubeda if needed. Ronda you can get to just fine with public transport.
I visited Andalucia without a car twice, but in hindsight I really wish we had had a car back then, and the next time we visit, we definitely will. The driving is not difficult. You would not want the car in Sevilla, but it would make your life markedly easier for most of the rest.

I can't recommend a private driver but I can give some advice and opinions on your itinerary.

Have you already purchased your airline tickets? We always buy open-jaw or multi-city tickets (fly into one city and out of another) so we don't have to waste time backtracking. And we spend x number of days in the city we arrived in, and we don't have to return to that city to fly home. But if you already purchased your tickets, then you can't do what we usually do. So, I think in your case, many people will recommend that you do not have 2 separate stays in Madrid. Once you arrive in Madrid, you should continue on to your first destination, such as Cordoba, as an example. And put all of your Madrid days at the end of the trip. This will give you more nights to play with. Whether or not you want to do this depends on what time you arrive in Madrid, and if you think you have the energy to push on to your first destination.

Do you have 22 days or 22 nights in Spain? 22 nights gives you 21 days on the ground in Spain. Since you have the time, I strongly recommend spending a night or two in Toledo. It is a very popular and very crowded city. The evening is magical in Toledo when the tour buses have left and the city is illuminated and Spanish families are enjoying the evening in Zocodover plaza.

I think 4-6 days in Seville is perfect! We spent 4 nights in Seville and I wish we had an extra night.

I recommend spending at least 2 nights in Cordoba and 2 nights in Granada. Cordoba is another city, like Toledo, that is so charming at night when the daytrippers have left and the city is illuminated. The Mezquita is magnificent but there is more to Cordoba than just the Mezquita. And ditto for Granada. Make sure you purchase your Alhambra tickets ASAP.

Madrid has some outstanding art museums and other interesting sites. I really enjoyed Madrid and think that 4-5 nights in Madrid is perfect. Definitely 5 nights if you want to take a day trip from Madrid.

I haven't been to the white towns so can't really offer advice except to say based on what I have read I think it would be easier to have a car or private driver rather than depend on public transportation in that area.

The trains and ALSA bus are wonderful modes of transportation. They are dependable, clean, comfortable and air-conditioned.

You will love this region of Spain! It's one of our favorite trips!

We are planning a similar for September. I am researching drivers between cities where the train connections are great. I’m looking at mydaytrip too. I’ve read some positive reviews. I’m also looking at toursbylocals.com. If I discover any more info I will private message you.

The simplest solution is what's already been proposed - go directly to Sevilla (4N) when you arrive. Buy tickets at the airport for the train from Madrid to Sevilla (they'll sell you the first train you can connect to) and will give you tickets for the train to Madrid that are included. Yes, it's a schlep but the train is comfortable so maybe you'll get some rest on the way. It may even be worthwhile to spend the 5th night in Sevilla at high prices just to get a sampling of the feria.

Then go to Jerez for 2-3N. Check if there's a horse show at the Royal Equestrian School. Visit several sherry bodegas (the Tio Pepe tour is the most fun). See the sights (cathedral, alcazar) and the shops selling flamenco dresses. Jerez is the capital of both sherry and flamenco. Day trip by bus to Arcos and by train to Cadiz. On to Ronda for 1-2N (there's enough to see to fill a full leisurely day) Google maps says 1.5 hours drive from Jerez to Ronda. With a driver you could enjoy the scenery and visit a couple hill towns on the way. Then bus or train to Granada 2-3N. 3N is better but a lot depends on the timing of your journey there from Ronda and on to Cordoba. IMO the Alhambra needs a full day. There's enough in the city cathedral, the Albaicin for a second day.

Cordoba is my favorite Spanish city. 3N is lovely. So is Toledo, so plan on 2N there as well. They both have a small town vibe unlike Sevilla or Madrid. End in Madrid - you'll want to be there on the night before your flight home anyway. If you love European painting, you'll want 2 full days in Madrid just for the art museums. Madrid is a nice enough city, but pales in comparison to many European capitals and many Spanish cities. If you have nights left (I haven't counted) in Madrid after your day trip to Zaragoza, day trip to Segovia.

Thanks very much for the great advice! We have decided to leave Madrid for the end of our trip, instead of breaking up the time there. I am looking most forward to the smaller cities, as you mentioned Chani, and perhaps we will bite the bullet, pay the extra $$ and experience some of the Feria in Sevilla. If anyone else has more suggestions, I’m always grateful for any help from those who have been there, done that! I haven’t been back to Spain in about 20 years! It was with a large tour group, so I feel like it will feel like a first time for me all over again! 😉🤗

We were in Spain for two weeks in December/January, and I used Spain Private Guides for one day's transportation. They were excellent.

Our trip was Toledo (2 Nights) to Granada (4N) to Cadiz (4N) to Cordoba (1N) then to Malaga and home. We used trains for all travel except for the Toledo to Granada leg. For that one, we would have had a long connection in Atocha and the total trip time would have been 7+ hours, plus there's not much to see from the train on that journey. I contacted Spain Private Guides (Dolca) via email, explained what I wanted (a private minibus for our group of 10, depart Toledo 9 a.m., stops in Consuegra and Baeza, with lunch and a private tour in Baeza, arrive in Granada around 7 p.m.). We got exactly what I wanted, plus some adjustments based on feedback from the guides, and had a lovely day that wasn't "wasted" sitting on a train with nothing to look at.

I would highly recommend getting in touch and seeing what they can do for you. They specialize in custom itineraries, so be specific in your request but also encourage suggestions; I received some valuable feedback during the planning that made our trip even better.

P.S. -- if you want to experience the Feria in Sevilla but avoid the accommodation cost, you could stay in Jerez or Cordoba and take the train in to Sevilla for the day. Then plan to stay in Sevilla either before or after the fair is over, whichever is more convenient for your final schedule. The Feria is really special, unique, and fun, but you don't necessarily need more than a day/evening of it to see what it's about.

Ubeda is a bit awkward to get to, as I believe you have already discovered. There's no rail station in Ubeda. Baeza is also worth seeing, but the Baeza train station is "Linares-Baeza", indicative of its location, which is not actually in Baeza. I traveled to, from and within that area by bus in 2019. I ended up spending my first night in Madrid so I didn't have to worry about catching the Ubeda bus; I had good intentions of doing some light sightseeing in Madrid but ended up spending 3 hours in a train-ticket line at Atocha Station. It would be a shame to have to do that on a 3-week trip when every day is precious, but perhaps you have an early arrival in Madrid and wouldn't have much concern about catching the bus.

Samar runs buses from Madrid-Estacion Sud to Ubeda. They are not frequent--currently departing at 9 AM and 3:30 PM. The trip takes 4 hours.

ALSA runs buses from Ubeda to Cordoba. They also operate just twice a day (if you ignore the 4:30 AM bus), at 9:30 AM and 3:45 PM. That trip is scheduled to take 2-1/2 hours.

Alternatively, ALSA runs seven buses a day (at least on the weekday I checked) to Granada. The travel time ranges from 2 hours to 2 hours 45 minutes.

I think it's a fine idea to consider a private transfer to manage the Ubeda part of the itinerary, though the buses are comfortable enough. I haven't read any negative comments about the DayTrip folks here (and haven't gone looking for any elsewhere), but be aware that they are an intermediary between travelers and transportation providers all over the place. Your driver would not be a DayTrip employee. This is a bit like booking a tour through Viator--the fact that other folks have loved tours they purchased through Viator doesn't mean the totally different tour you choose will be equally wonderful. That said, if I had the money to do so (things like that are really costly for a solo traveler), I wouldn't hesitate to use DayTrip for hard-to-reach destinations.

Arcos de la Frontera is accessible by bus from Jerez (by far the closest and fastest), Seville and Ronda. Because the bus frequency from Jerez is so much greater, a train/bus combo (changing in Jerez) is worth considering. You can find the Damas Bus 951 and 952 schedules for Jerez-Arcos here: https://siu.cmtbc.es/en/horarios_lineas.php.

I've found the local tourist offices often have handouts showing bus schedules to destinations of tourist interest. I always verify that information online (or by stopping by the bus station if that's convenient), but generally the T.O. handouts are accurate.