I always get overwhelmed when I have to write a guide for cities when I live in because there are just too many places I love. Visiting is easy, but living is harder.
Salmon Guru: The most extravagant cocktails, creative and delicious
Celso Y Manolo: really fresh ingredients, especially the tomatoes-- my favorite dish is the chuleton de tomate de huesca con seis cosas ricas
Pez Tortilla: A number of locations, but great IPA and other craft beers and the best jamon/truffle/brie tortilla!
Casa Julio: smaller restaurant, first come first serve but get as many croquettes as possible!
El Cisne Azul: one of the oldest restaurants in Madrid, it focuses on mushrooms
Angelita: Delicious cocktails, fancier Spanish far
Rooftops
Casa Suecia: Smaller rooftop but a lot more chill, in the NH
Toledo
It's a hike up, if you don't have a car, but it is 100% worth it to go to the Mirador del Valle.
You should spend at least 2 hours in Santa Iglesia Catedral Primada de Toledo, and it comes with audioguide, since this church really is a behemoth.
My favorite part of the Monasterio de San Juan de los Reyes is the Isabel and Ferdinand really scrawled their love all the walls. Their motto was tanto manto - monta tanto and really spoke to their equality and partnership. They are some really funny-shaped gargoyles on the second floor.
On your way to Sinagoga de Santa María La Blanca, notice the little ceramic tiles on the pavement that show you're in the jewish district. When the synagogue was re-purposed, they only left one jewish star. Can you find it?
El Greco's real name is crazy hard to pronounce, but he spent most of his life in Toledo to really refine his artistic style. The El Greco museum is both extensive and informative.
Valencia
Valencia is a charming little city, but I wouldn't spend more than 2 days there. You can either stay in El Carmen, the old city, or in Russafa, where are the cool bars are.
I actually didn’t go the beach when I was there, but I hear the beaches are calm and pretty nice. The Ice Factory (La Fabrica Hielo) is a cool independent cultural space close to the beach to check out as well.
Rent a bike and bike to the Ciudad de las Artes y las Ciencias, where the famous sci-fi looking buildings are (this place is super fun to do a photoshoot around) and then all the way to the end of the old riverbed, Turia. So many great spots for picnics in the this park!
La Manera: great for a breezy lunch and some fun cocktails
Kuzina: Simple, but high quality Greek staples
Horchateria Santa Catalina: Famous horchata place
Segovia
If you are driving, on the way Segovia, you can either visit San Lorenzo de El Escorial or La Granja De San Ildefonso Royal Palace. El Escorial has a super cool library and a lot of different architectural styles. It is nestled in the mountains and has lovely surrounding . San Ildefonso is a more a palace with grounds, and it's closer to Segovia.
In Segovia, the three main attractions-- the aqueduct, the cathedral, and the palace are about a 20 min walk from each other. I found the inside of the Alcazar very boring, but then you can see a great scene of the entire castle from the Mirador.