Madrid - Museos: Madrid is basically the DC of Spain and it shows this in historical museum quality. If you want Velasquez (Las Meninas is amazing) and Goya head to the Prado; if you want Picasso and Dali head to the contemporary museum. If you want to see palaces they have a grand one along with a big Plaza Mayor (expensive real estate!!!). Either way Spain kept most of its culture and history by holding onto its artwork and artifacts. As such, you will enjoy the amount of stunning pieces from the Spanish museums.
Madrid - Tapas Bar Hopping: If you're going to bar hop with tapas, this is the place to do it. Though some argue for Barcelona, I think there are two really good areas in Madrid that have tapas bars next to them for you to have some fun with a drink and a little plate. The array of dishes led to amazing Ribeiro wine, pimentos de pedron, orelhas de porcos, manchego cheese, baranjas (eggplants with carmel), octopus, squid, anchovies, and Iberico ham. It was a feast and the drinks were pretty good too. As a result, watching my mom and dad get drunk was hilarious as my mom stumbled a bit. I was also getting tipsy as I tried tagalog with some Filipinos (ex-Spanish colony after all). Wonderful times with parents and amazing food and drink, seriously one of the best bar-hopping spots in the world.
Toledo - City of Religion: Toledo once a supremely holy city due to Moors following Islam, Jews, and Christians all living together. While the city has been through a few different sets of turmoils including kicking out Muslims and Jews and then reaccepting them, the city is a diverse look at religious freedom long before the 21st century mindset. There are synagogues and churches and possibly even a mosque. The Cathedral looms large, but there is also an extremely interesting chapel that Ferdinand and Isabella used to demonize nearly all non-Christians and anyone who wasn't in their favor. As such, I learned that they were both as awful as that one guy they sent in 1492 for discoveries.
Cordoba - Mezquita: On the way to Sevilla from Madrid, you can stop in Cordoba (a little further and you can head to Granada to see the Alhambra) to see one of the finest religious structures you will ever see. The Mezquita, a mosque with a cathedral in the certain is a blend of ordinance, symmetry and proof that religion can coexist. Moors (Maghrebs) built mosques, but then the Spaniards wanted a church, but liked the mosque so much they left it. The limestone archways are also a site to behold and are the trademark of the landmark.
Sevilla - Stroll: Sevilla is another city like Florence, Cuzco and Kyoto that is wonderful to take a walk in. Sure the Alcazar (Game of Thrones!), the huge Cathedral (largest one and where that Cristobal Colon fool is buried - strange how I've charted his journey), and the bullfighting ring are wonderful, but it's a lot of fun just to walk in the calm streets. As such, you will have a good time sipping sangria, watching Flamenco, and walking through old churches mixed with modern apartments.
Barcelona - Catalan Modernism and the Bustling City: I love Barcelona, as a matter of fact it is one of my favorite cities in the whole world. This is primarily because it functions like NYC in its nightlife (which I was too sick to really see), it's variety of buildings - including all the Gaudi with La Pedrera and Parc Guell, Picasso's origins (great little museum here for his Spanish work) and Las Ramblas. Apparently, there is also a wonderful beach, Barceloneta, and a mountainous area, Montjuic. However, I have to give a major shout out to a city that impressed me even though I didn't go out, fully explore nor have all the authentic food of either. The Catalan language sounds bizarre and thankfully they understand Spanish (good luck trying Catalan), but the city is a blast and I did at least love the Bosque County tapas, canapes and Obama (I'll miss him!) cigar shop.
Barcelona - Sagrada Familia: This is one of the most epic cathedrals, monuments or landmarks in the world. Gaudi started it before his death and it has been slowly finished by other architects since then. The sides of the church, the steeples, and the interior are all just about finished. However, there's more to do even to the front area. As such, it is gaudy(hah) and abundant in its flourishes of religious quotes, symbols, designs, stained glass, detailed facades, fruit ornaments, stairs, pillars and more. It is also the symbol of Barcelona like the Eiffel Tower to Paris and as such can be see from anywhere in Barcelona. It is a powerful and well-designed structure that has a legacy that demands attention. Hopefully it gets finished!
Azores - Terceira Island: Minha mae's ilha! (My mom's island). This is where my mom was born and as such was an amazingly personal journey for me to see where she grew up. We didn't get access into the Lajes Air Base where her family directly grew up, but we got to see Praia and Angra where she went to the beach and church respectively. We also got to see gorgeous hydragengas and burned out volcanoes. Mom also splurged for this fancy hotel in the Azores to go big for her homecoming. It was overall a peaceful trip where I got to learn more about stick-shift driving old cars while loving the peaceful seaside towns of Angra and Praia.
Porto - Duoro Valley and Riviera: Port wine is some of the best wine in the world and not just because it's Portuguese (granted most pieces of Portugal I LOVE). Still, I highly recommend a port wine tour in the Valley to see the land and try one of the port wine companies (Sandeman if you can't find anything else). The tawny port is strong, the rose port is easier to work with, but overall they're all sweet and wonderful wines. After you return from the Valley, you have to check out the Riviera for the boats, the port wine factories across the river, bacalhau, Vasco Da Gama's house, (Portuguese explorer, but Bartholomeu Dias started the slave trade, so hate on him) and this cross-cultural stock exchange with a Moorish room, US influences, and blue prints from the architect of the Eiffel Tower, Statue of Liberty and some Porto bridges. There's also lots of good shopping in Porto, but the Riviera is great to relax around.
Portugal - Nazare, Coimbra and middle Portugal: Portugal is not that large of a country (from top to bottom it will take you probably 7-9 hours), but the middle of the country has several intriguing little cities that are different than Porto and Lisboa. Coimbra is known for its university that still houses original books that are about 500 years old. Some of the other areas are known for their ginja (a great liquor that is better in Alcobaca and Nazare rather than Lisboa). Lastly, in Nazare, we would see my mom's cousin who brought back all this Portuguese from her. I was stunned, 26 years of never hearing her speak it and she brings it out as if it's nothing. My mom had tears for reminiscing about her parents in Portuguese and at first I was angry that she had never brought it up, but then I was happy that she did now. This was huge since now my mom talk and email in Portuguese every now and then!
Portugal - Lisboa: Once again, this city (Lisbon) is not one of my favorites because it's Portuguese. I like this city because it is unexpectedly fascinating. You're thinking that this is going to be some grand tourist European city, but it is not at all. Instead, it is filled with a diverse crowd (Portugal is very friendly to countries they once colonized), distinct neighborhoods - Alfama (Eastern European crowd), Barrio Alto (churches and graffiti), and el baixo (squares and barracks), and some fun nightlife areas like the Pink Zone that was once a shady sailor hangout. In Lisboa, I hung out with family, had some glorious Portuguese (great seafood, but they leave the animals intact) and Brazilian cuisine, watched burlesque, saw the shrine to Eusebio, and saw the Benfica stadium. It was quirky, but it was great time overall and I recommend the city for everyone.
Lisboa - Sintra and Belem: Both of these places are a quick train ride and taxi ride respectively from Lisboa. Belem has the amazing Manueline (a Portuguese design institution) monastery, a monument to Portuguese exploration and world map. This is also where you can buy some of the best Pasteis de Natal (glorious egg custards). Sintra is a standout for its grand palace with a mix-match of designs and the last bastion for royalty in Portugal.