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Notes -
Dang! What's on the itinerary? I have never even left the country. Though when I visit relatives in other cities, I guess they typically plan trips for me, and they usually involve going to restaurants that they want to show me and certain landmarks. I suppose that's how visiting a foreign city would be, too...
I’m there for a week before I go with my family to visit our extended family in north England. I haven’t made a detailed itinerary because that feels too much like work. Have a few restaurants and museums I want to go to, a run club on Wednesday night (classic Spaniards not even starting until 8pm) and day trips to Toledo and Él Escorial).
Personally I find planning for a holiday pretty entertaining. I'm travelling on the 15th too; going to China, and the number of places I have written down is ridiculous and I will probably will not be able to visit them all. If I were in Madrid I would at least visit the following:
There's also the Temple of Debod, an Egyptian temple moved straight from Aswan to Madrid, the Cerralbo Museum, a private mansion containing the private art collection of the Marquis of Cerralbo, alongside a bunch of other museums and palaces that are worth visiting if you have time.
If you're willing, a trip to Toledo is just a 30 minute train ride away. It's a historic town that's on the UNESCO register; its centrepiece is the Primate Cathedral of Saint Mary of Toledo, a High Gothic church (one of the only three in Spain) featuring a gigantic carved altarpiece. I'd say it may be worth your time; there are many other historic sites, synagogues and even former mosques in the city from the Moorish period. Just walking around the old town and checking out whatever you can would probably be rather fun.
I never plan much when I go on vacation, usually I have like 1-2 things I want to do when I go for a week and let the rest be spontaneous.
My father-in-law does a minute plan whenever he travels. It can be fun following him around for like a day but then it gets exhausting and counter to the purpose of going on vacation in the first place (for me).
I don't really disagree with that, rigidly planning out every moment of your vacation is an absolute and utter slog. But I never really have an exceptionally clear idea of what I would want to do on a day by day basis; I don't plan things out for the purposes of prescriptively defining what my vacation should look like. My kind of planning looks more like keeping a register of what's there so I can make an informed decision of where to go in the moment (which doesn't exclude exploratively walking around and seeing what's there, either).
It's also particularly important to understand what's in your vicinity when you're vacationing in a more rural area, since unlike a city it's harder to just walk around and stumble across things spontaneously.
That being said, I do get the sense I like to travel in a significantly more hectic way than most people. I get bored very easily just kind of lazing around for a significant portion of the time; beach and cruise vacations are exceptionally unappealing to me.
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