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You must try Pikayo in Condado, it's a great place to have dinner. The chef was featured on Top Chef Masters, expensive but worth it.
La Bombonera in Old San Juan for breakfast. One of the oldest institutions in San Juan. Their "mallorcas" are a must.
Raices in Old San Juan is where you will get the most authentic feel. Start with one of their samplers there you will get a taste of many of their fritters (sorullitos, alcapurrias, bolitas de queso, etc) and then have one of their amazing stuffed mofongos. This place is great for someone that is visiting.
http://www.restauranteraices.com/If you have a car available, you MUSTT!!! go to Guavate. It is pork heaven. Guavate is located in the mountains of Cayey (30 min drive from San Juan) and it is filled with different vendors they are all good and offer the same variety of food (Lechon, arroz con gandules, morcilla, guineitos en escabeche, etc
)Another great place very close to Condado is La Placita de Santurce, it is a food market where you will see all sorts of local fruits and vegetables. If you are looking to eat great seafood then go to El Pescador, a great seafood restaurant right in front of the Plaza. If you go to La Placita and don't want to eat heavy then have a drink at El Coco de Luis (great natural juices, have a vodka with toronja) and then nibble on some amazing chicharrones de pollo con tostones. you won't regret it.
By the way, I don't know for how long you are staying, but there is the most beautiful island off the coast of Puerto Rico called "Culebra". It is a 20 min plane ride from Isla Verde Airport and it has some of the world's most spectacular beaches.
Enjoy your time in Puerto Rico! I am Puerto Rican so trust me with these places you will love them!
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re: Jeff C.
MJ's feisty ex-pat, she runs a cart that sells her Island Woman Hot Sauce. but I gotta echo mcolon's comments about that little island, drop dead gorgeous beaches that unless it's a big holiday, are almost deserted. food can be hit or miss, but Tina's el Caobo, usu. has only 2 things on the menu is worthwhile and the burger at el Batey will take 45 minutes and the locals will be served before you, but it's damn good, good grazing choices at the main beach, pinchos, pastellitos, etc. if you have a coupla days it is worth the side trip if only to hang out at the Dinghy Dock for cocktails at sunset.
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re: Jeff C.
Condado has some small but nice beaches, all sorts of little cafes within a block or 2 and is an easy bus ride or cab trip into OSJ. the only one in Condado I recall by name was Ajillo Mojillo and it was alright (but then I was sun blasted after week on the beaches of Culebra). the area of Isla Verde is a lot swankier.
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re: Jeff C.
I dont recommend going to the beach in San Juan, the beach there is more of a surfers beach, by that I mean that is very choppy and not good for a relaxing swim. I recommend you go to Ocean Park in Condado and have lunch at Pamela's right on the sand.
I also forgot to mention Drangonfly in San Juan for dinner. Its great!
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