First time in Spain... need some advice!!

Need more info to give good info...

1. Have you ever been to Europe before? If so, where?

2. Where are you coming from (flying in to Madrid)?

That said, I have some serious concerns about your proposal..

1. I think the overall pace of your trip is quite unrealistic. Even if you are able to physically do it, it sounds like a grim death-march to me. You can't slice days like that: "fly to place X in the morning, spend a few hours exploring, sleep, get up and move on to someplace else, repeat"). Going in November, your days will be short, compounding the challenges.

2. If you will be arriving on a long flight (say, from North America or other place far away), you're not going to see or experience much of Toledo that first day, except horrible crowds. As you are proposing, you will experience Toledo at it's absolute worst: at it's most crowded (mid day, jammed with day-trippers). Due to jet lag and exhaustion, you will crash and burn early, missing your best chance to get a glimpse of this wonderful city without the streets being jammed with tour crowds.

3. You will never really get a chance to actually spend a whole day anywhere. In fact, I would worry if you will ever recover from the initial jetlag from your arrival flight. If you push on relentlessly at such a punishing pace, that can leave everyone miserable. Any kids or non-expert travelers in your group? Remember, any group only moves at the pace of its slowest member.

Going to Spain in nov for about 10 nights...

No, you're not. You're going to Spain for 5 days. You are not being honest with yourself about this. The day you arrive nor the day you move on with the rest of your trip are not usable days.

With just 5 full, usable days in Spain, you should pick no more than two locations. You need to account for the fact that every time you pick up and move, you will burn most of a day. You're starting in Madrid and ending in Barcelona. There are your two locations - that's it. You will have 2 full days in each, that's all, and you have one day when you will move between them. Be realistic.

I know this is not what you want to hear. Sorry.

Forget San Sebastián. You really don’t have time, and November is not ideal.

Day 1: 8am arrival in Madrid (3)
Day 2: Day by train to Toledo
Day 3: Madrid
Day 4: Early train to Seville (3)
Day 5: Seville
Day 6: Day by train to Córdoba
Day 7: Fly from Seville to Barcelona

David, I definitely have 10 days because I’ve already taken out my flying into Spain and flying out of Spain time!

Been to Italy a few times and actually did more in less!

When I travel I don’t think abou my jet lag as I’m there to explore. I sleep on trains as a means of resting and use my day wisely. Most people suggest Toledo as a day trip from Madrid. Go in the morning and come back in the evening. I’m considering to do over night so I can experience the night life there!

Why is San Sebastián not ideal for November? Not going for the beaches but the culinary experience. And I think culinary is something that’s great all year long, right ?

For me, miserable weather makes for a miserable stay, beach or no beach.
Half a day travelling from Madrid to San Sebastián, and half a day travelling from San Sebastián to Barcelona, is too much time invested for just one day’s time returned at your destination.
To attempt four destinations - Madrid, Toledo, Seville, San Sebastián - in just six days, is just plain folly.

I definitely have 10 days because I’ve already taken out my flying into Spain and flying out of Spain time!

Respectfully, no, I don't think you have. Look:

Day 1:Landing in Madrid around 8 am ( thought is to go straight to Toledo and check in at a hotel there, drop luggage and then go out and explore the town).

Day 2: finish up in Toledo (if need be) and head to Seville or go back to Madrid?

So, what you are calling "Day 1" is the day you fly in (from where? a redeye overnight from the other side of the world?), then you say you will push on to Toledo, and that will be your day to see Toledo. Then the next day (which is what I would consider your first actual day in Europe), you will get up and maybe see some more of Toledo "if needed" before you pick up and move to "Madrid/Seville."

Then you have what you call "Day 2" through "Day 7"...how does that math work where you end up with 10 days in Spain? "Nights" are not generally usable sightseeing time - days are.

I sleep on trains as a means of resting and use my day wisely.

Oh-kay...

Most people suggest Toledo as a day trip from Madrid. Go in the morning and come back in the evening. I’m considering to do over night so I can experience the night life there!

I am a fierce advocate of not doing Toledo as a day trip, and I do agree that spending the night there is the best way to experience Toledo. But that assumes you are awake and able to appreciate the place without the day trip crowds, not doing the jetlagged zombie shuffle, and just looking forward to hitting the bed for your first real sleep since you left home about 2 days before. If you and your travel companions all sleep well on the flight over, and all are immune to jetlag, well, lucky you, many of us would be envious. I'd be careful about assuming all of that though, and building in a very aggressive schedule assuming you will all hit the ground running and get in a full day of sightseeing after your redeye arrival.

I believe you are not being realistic. But you know yourself and your travel partners better than me, and it's your trip. Spain is wonderful. Good luck and I hope you enjoy it all.

I agree with the others that this is too much in too little time. San Sebastian is especially problematic because the transportation is time-consuming in both directions, from Madrid and to Barcelona. Flying requires transportation to and from airports, plus (I assume) arriving at the airport at least 2 hours early. And of course you have the hotel procedures on both ends. You'll lose over half a day going into and out of San Sebastian. Both Barcelona and Madrid have great restaurants. Skip SS until you can spend more time there at a more pleasant time of year.

You also are apparently allowing very little time in Barcelona, which is a very sight-rich destination. Because of its massive popularity, pre-purchased (usually timed) tickets are needed for many of its top sights. It is impossible to know precisely how much time you'll want to spend at each site, so you cannot create a maximally efficient sightseeing schedule. Barcelona is not an easy place for very short visits.