Spain Itinerary Questions

I think you are going to need to cut back. Try mapping out where you will spend your nights, how much time you will need for transportation from place to place and how much time is left for sightseeing. RS itineraries are too fast-paced for me. Don't try to go faster than his whirlwind suggestions.

If one could find a way to start in San Sebastian that would make this easier.
We did El Escorial and Segovia together as one day trip from Madrid by car; you may not need to cut it.
We also did Toledo as a day trip from Madrid. Madrid is just ok; it is a museum painting town so those daytrips worked.
Cut Tangier; people seem to tend to include it in a trip to Spain to say they've been to Morocco.

I haven't been to Tangier, but just from looking at your list I would save it for another trip.

Also consider dropping Logrono and San Sebastian, and substituting the awesome Priorat wine country as a day trip from Barcelona.

On our 17 day trip to Spain in October 2017, we only slept in Madrid, Seville and Barcelona - with day trips to Segovia, Jerez de la Frontera/Cadiz, Priorat wine country, Tarragona/Sitges, and Girona/Costa Brava.

The reality is that you really can't fit in everything that you want to see on any trip.

Reasonable minds differ - And unlike Jazz+Travels, I loved Madrid!

Those are a lot of places for the limited time you have and they are spread out throughout the country, thereby increasing the total amount of time needed to get to them. I’d eliminate Tangier right away because it sits off by itself in North Africa. The first four on your list are in close proximity, as are Barcelona and Monserrat, and Sevilla and Córdoba. San Sebastián is off on it’s own as are Logrono and Granada. You just need to decide if the time it will take to get to those places is worth taking away from the rest of the trip. How you’re getting to the places will also help determine how many you’ll get to see. Public transportation or rental car, and are you taking day trips from a base location or changing hotels every night. If you’ve been to any of them previously then possibly eliminate them. If it was my trip, and my first trip to Spain, I’d keep those in close proximity to each other and eliminate San Sebastián, Logrono, Tangier, and Granada. I hate eliminating Granada because everybody should experience it at least once.

Is it possible? No! Even if you really have 16 days on the ground, traveling between places would eat up too much time. Spain is a big country.
My first suggestion is that you book open jaw* flights; e.g., into Madrid and out of Barcelona. That will save a day that would otherwise be spent getting back to where you started. Next scratch Tangier, San Sebastián, and Logrono. I would have three base cities; Madrid, Seville, and Barcelona. Cordoba can be done as a day trip from Seville; Toledo, from Madrid. Segovia is also close to Madrid, but I don’t remember if it’s close enough for a day trip. You could possibly add in Granada. The Alhambra is just too spectacular to miss.
You’ve given no clues as to your interests, but you should sit down with some guidebooks (older editions from your local library will do), and figure out what you want to do/see. Then you’ll have a better idea of how many days to allot for each base Or, check on Tripadvisor for each base under “things to do.”

*If you don’t know what this is and how to do it, come back and ask.

When will you be in Spain? Andalucía often has brutally hot weather in the summer. When trimming the itinerary (see below), I'd give some weight to weather expectations.

How many nights will you be spending on the ground in Spain?

The reason you're having trouble putting together a workable itinerary is that it cannot be done if you want actually to see much of anything in those places.

First, eliminate Tangier. It means a good part of a day getting into position so you can take a ferry to Tangier, spend some time in that not-great city and then take a ferry back on the second day. Then you'll need some time on a third day just to get to the next Spanish destination on your list. Morocco is a wonderful place, but Tangier is a port town that doesn't have as much to offer as many other Moroccan cities. It really isn't worth giving up such a big chunk of your trip.

The cities of Barcelona, Madrid, Cordoba and Seville are well-connected by fast trains, making them the easiest to visit from a time perspective. It is also easy to get to Montserrat from Barcelona and to Toledo/Segovia/El Escorial from Madrid. If need be, Cordoba can be visited as a day-trip from Seville; that allows you to eliminate one hotel change.

Ease of transportation doesn't mean you must go to those places or only those places, but keep in mind that the time you spend on trains and buses is time you are not sightseeing (you're not generally going to be traveling through spectacular scenery).

Granada is without a doubt one of the very top sights in Spain (arguably the #1 sight). I think you can squeeze in the two nights you need in Granada to visit the Alhambra, assuming you can get tickets. Alhambra tickets sell out very early.

Including Logrono and San Sebastian will require cuts elsewhere, so it depends on your priorities and--I would suggest--the weather. I'm not sure about Logrono, but San Sebastian is usually not very hot even in midsummer.

This is like putting a puzzle together, but you need to know how much time you want to spend at each destination, and that's where your sightseeing interests are critical, especially:

- How interested are you in Madrid's art museums?
- How interested are you in Barcelona's modernista sights?

Keep in mind that the day you arrive from the US/Canada you may well be severely sleep-deprived and jetlagged, so that day may not be a very productive one, beyond just wandering around outdoors, trying to stay awake.

Also, every time you pick up your luggage and head to a different hotel, you're losing at least half a day. The trip between Barcelona and San Sebastian will cost considerably more time than that.

You can explore travel times on the Deutsche Bahn website, though you'll need Renfe to see fares.

Thank you all for your swift and insightful responses thus far. Adding more information about our trip and interests probably would have been helpful. We are planning on going late May through early June. The things we are most interested in are architecture, food/wine, and horses. We also love scenery and the beach. As far as museums go, we enjoy them, but typically can only do 1-2/day before we start to get bored. We will also be traveling by train and bus.

If you like horses, Jerez de la Frontera should definitely be on your itinerary!

If you have 16 nights on the ground in Spain then this gets you to all except Tangier and Rioja.

Day
1. ARRIVE Barcelona (4N)
2. Barcelona
3. Barcelona / Montserrat
4. Barcelona
5. Fly to San Sebastián (2N)
6. San Sebastián
7. Fly via Madrid to Granada (2N)
8. Visit the Alhambra
9. Train to Seville (3N)
10. Seville
11. Seville
12. Train via stop in Cordoba for the Mezquita, then on to Madrid (5N)
13. Madrid
14. Day to Toledo
15. Madrid / El Escorial
16. Day to Segovia
17. DEPART Madrid

Personally I wouldn’t find it worthwhile for 2 nights in San Sebastián, with the additional hassle of flying. I would add an extra night in both Barcelona and Seville.

If horses are a main interest, visit the Royal Equestrian School in Jerez (possible to day trip from Sevilla by train), on a day when there's a show. Go early and see the horses in the paddocks before the show. The Royal Stables in Cordoba also have (somewhat different) horse shows several evenings a week.