I would use this to get around: Ten toes. The city has lots to offer in the way of colonial architecture, artisan shops and sidewalk vendors – you’ll be missing out if you do anything but wander the town centre on foot. The only reason you’d need a taxi would be to get to and from the bus terminal or airport, and a bus is required to get to the surrounding areas if you’re heading out on a little field trip to the ruins of Mitla or Monte Alban.
I would stay here: Generally, you want to be within walking distance of the Zócalo and catedral Santo Domingo. Tip: Most of the cheaper hotels and backpacker hostels are located to the south and the swankier hotels further north. If you’re heading into town for Día de los Muertos, check to make sure that your hotel/hostel has an organized cemetery tour. It will increase your level of interaction and enjoyment during the whole event by a lot. Like, maybe 72%. That’s pretty good.
I would eat here: Oaxaca is Mexico’s capital of foodstuffs, so there are oodles* of great restaurants. (*1 oodle = about 20) Regional specialties include Oaxacan cheese and mole (rhymes with olé or guacamole or Hole A), which is a sauce that contains a delicious amount of chocolate and is served as a sort of edible blanket atop chicken, rice, pork, lamb, your fingers, a fry you stole off your boyfriend’s plate, whatever. I had a great meal at Hostería de Alcalá, almost directly across from the cathedral, but you can find mole in pretty much every single la-ti-da restaurant in the centre of town. In other news, be sure to hit up the market for some local cheap eats. Tamales are common and delicious, empanadas are everywhere and, if you’re feeling adventurous, you could go for some grasshoppers, or chapulines. They are surprisingly not gross, although I would put them on the list of things that I’ve done once and maybe don’t need to do again. There’s also a café on Alcalá about half way between the zócolo and the cathedral called Café Brujula that serves great coffee and yummy treats in an airy little courtyard with free wi-fi. Hit it.
I would drink here: There’s a tiny street directly across from the cathedral that has a few rooftop patios and small bars which are pretty lively and offer great views of the square at night. Nestled among them is a little mezcaleria, which is basically a cozy little closet, the walls of which are lined with a massive variety of mezcal for your sipping pleasure. (Mezcal, for those who don’t know, is a local liquor in the same family as Tequila, but a bit more potent and a lot more pure.) Definitely worth a swig or eight. There’s also a spot up around the bend on Avenida García Vigil that is super popular with the in-crowd. La Biznaga has a large bar, large tables and large margaritas. There are also some really nice little shops in the space surrounding the courtyard selling artisan crafts and clothes which are a bit different than the typical street-side fare. I liked this place a whole lot and wished I had friends to share it with because that seems to be the thing to do here. (Don’t get me wrong: I do have friends. Just not in Oaxaca.)
I would do this: Plan to go to Oaxaca during the Day of the Dead, or Día de los Muertos. It’s a really fantastic cultural event unique to Mexico, making this one of the very best spots to be when the calendar flips from October to November. Many Mexicans have a belief that once a year on October 31st, while the rest of us are dressing up like slutty nurses and drinking our weight in vodka sodas, the souls of their loved ones return home for a visit from beyond the grave. They head to local cemeteries and hold vigil for one, two and sometimes three nights to light the way for their beloved visitors and welcome them back with sweet breads, candy and flowers. It’s a city-wide fiesta on a grand and glorious scale, complete with Mariachi bands, food vendors and, of course, a fair amount of alcohol. The sort of mascot of Dia de los Muertos is La Catrina, an elegant and beautiful skeleton woman with roots in the vibrant Mexican art scene and the bloody Mexican Revolution. She’s everywhere during the celebration, similar to Santa Claus at Christmas, but way skinnier and definitely way creepier if caught crawling down your chimney in the middle of the night.
I wouldn’t do this: Imagine that you can just blow into town on October 30th and score a room in Oaxaca for Día de los Muertos. Book your accommodations well in advance to ensure that you get a spot that’s both close to the good action (Day of the Dead) and far from the bad action (generally seedy activities like muggings and such).