Huge thank you to this board for all the reviews and suggestions posted; a good amount of my trip was planned based on findings from this board. My friends were very impressed! We ate A LOT, so I will try and be concise and point out the highlights. We made reservations before the trip for Le Cabrera, Bodegon Alejandro, Hisop and Tickets.
Day 1 dinner: Tapas in La Latina - we visited Txirimiri, Txacoli, Txacolina, Tempranillo, mostly on Cava Baja. While everything was good, nothing was particularly memorable. I would have liked to try more things on the Txirimiri menu
Day 2 lunch: La Plateria before visiting the Prado across the street. Great hangover type of brunch food: had excellent eggs, potatoes and chorizo and fabada, a sort of pork and bean stew. A little expensive but not surprising given the location
Day 2 dinner: Le Cabrera. Liked the decor of this place, the chef was really nice, though some patrons had attitudes. Particularly loved the bombon de carne, croquetas and the deconstructed cheesecake dessert.
Day 3 dinner: Bodegon Alejandro. Really enjoyed the warmth of this place and the food. Might be my favorite meal; I just found the food to be so satisfying. Overall, I enjoyed the pace of the sit-down meals in San Sebastian more than in other cities; it was much more slow and relaxed and I felt like we could really savor every delicious bite. We ordered the 38 euro prix fixe, favorite dishes was the tomato stuffed with squid over squid ink and cheese rice and the iced coconut rum / chocolate / ice cream dessert.
Day 4 dinner: Pintxos crawl in Parte Vieja. Unfortunately given that it was Feb and a Sunday night, many places that we wanted to try just weren't open (a fuego nero, zaruko, ganbara, txepetxa). I should also mention that many of the sitdown restaurants that we wanted to try were also closed for February (like Kokotxa and Akelarre). We tried Tamboril, Bar Martinez, Gandarias for dinner and Aralar for breakfast. All were good, but no particular standouts.
Day 5 dinner: Urepel. This was a lovely surprise as we didn't have a reservation, just walked in, but had a wonderful, thoughtful meal. Also a good value at 50 euro prix fixe including drinks. Favorite dishes was the yogurt ham salad and the cubes of suckling pig.
Day 6 lunch: Bar Pinotxo in the Boqueria. We arrived a little late, around 3pm, so unfortunately many stalls were closing and there wasn't a huge selection at Bar Pinotxo. Still enjoyed our simple meal with chickpeas, langoustine and anchovy salad. Fresh seafood simply cooked and dressed.
Day 6 Dinner: Hisop. Maybe my expectations were too high, but a bit of a disappointing meal. Perhaps our mistake was ordering a la carte; did not like the lamb chops (almost impossible to chew because they were so rare) and the pigeon with truffle surprise was surprisingly ordinary. I liked the "after eight" foie gras (shaved mint chocolate over foie), but I like anything foie.
Day 7 Dinner: Tickets. Fun food and atmosphere. Favorite dishes were the olives, tomato and strawberry salad, bonito with gelatin. Lots more that I would have liked to try on the menu.
Wonderful trip with lots of wonderful food and people. It was a lot of food over the week and it probably would have all blended together had I not captured it in pictures. For more detailed reviews and photos, please feel free check out the attached (although warning, all very long)