Cool stuff to do in Tucson:
Frank's Restaurant (3843 E. Pima) -
This place is the platonic ideal of a greasy spoon breakfast joint. Every southwestern breakfast classic served in a tiny, ramshackle venue. Amazing biscuits and gravy, fantastic huevos rancheros, and cheap prices.
Tucson Tamale Company (2545 E. Broadway) -
A local favorite that only serves tamales of a plethora of varieties. No beer or wine and closes around 5PM, so this place is the perfect quick, cheap lunch restaurant. Two tamales and a soda make the perfect lunch. The cold rice salad is actually pretty amazing too. Order as many different types as possible with your group and share. The green corn was fantastic as was the Tucson.
Cafe Poc Cosa (110 East Pennington Street) -
This is a fantastical southwestern restaurant. The food here is literally changed twice daily on chalkboards that are brought to the tables. A bit pricey, but by far the most innovative and important restaurant working with Mexican cuisine in Tucson. Average entree price is around $25, so this is a bit more expensive than most places, but the various preparations of mole sauce or curious use of obscure chiles make this a true gem. The pear cobbler desert is perfect for those of us who like our deserts less-than-sweet. Worth making a reservation. For some reason I felt that the margaritas were a touch weak (though I felt this way about most of the establishments in Tucson).
Guadalajara Grill (1220 East Prince Road) -
Well above average Southwestern Mexican food. Plenty of neat dishes with twists (like a tilapia in a poblano cream sauce) and a fun selection of enchilada combination plates that are a great start to any trip. The margaritas were fairly nice here. Notable for two reasons: 1) They use a mortar and pestle to make salsa fresh at your table side. 2) They are actually open on Sunday night. A great alternative to El Charro (which only shines with it's Carne Seca dishes).
Hotel Congress / Cup Cafe (311 East Congress Street) -
An old-west hotel that is rumored to be haunted. The food here is really solid, if not jaw-dropping, Americana with a Southwest flare. But of more note is the large selection of classic and invented cocktails made with a deep passion for mixology. The invented cocktails tend to be a bit on the simplistic side, but the classics tend to be impeccably balanced and flavorful. Certainly a classy place to start your evening. Also, I was once locked in a bathroom in one of the tiny old hotel rooms on a road trip. I don't know about the haunted part, but hotel staff was surprisingly understanding when I handed them the doorknob and explained how I had to kick the door in to escape.
El Guero Canelo ( 5201 South 12th Avenue, Tucso) -
"Geuro" is pronounced "weh doe" btw. This is THE singular place for Sonoran hotdogs in Arizona. Which if you don't know are a Mexican invention of a bacon wrapped dog with beans, chiles, cheese, mayo, onions and other items. In old Tucson (which looks like a rundown industrial district from Mad Max) this place is worth the drive just to grab a couple of dogs and hang out on the tented porch. Open until midnight.
Kon Tiki (4625 East Broadway Boulevard) -
Tucson's favorite spot for strong, fruity drinks. While probably not, heck, certainly not, the best nor most authentic Tiki bar around, it's a fun place to stop in for a couple of drinks on a lazy weeknight where you have no where else to be, and want to get slightly tipsy and ramble. Cute tropical interior with many nooks and crannies and fake palm trees. Designated driver warning: these drinks might taste girly, but some are exceptionally strong (especially any at $6+) so make sure to have someone who only plans to have a drink or two handy with the keys.
Center For Creative Photography (Park at the NE corner of Speedway Blvd. and Park Ave.) -
This is one of the strongest collections of art photography in America. Located on the university campus, this free museums feature free admission and rotating shows. Very near the university art museum as well, so if you are up for it, make it an art twofer.
The Surly Wench (424 North 4th Avenue) -
This decidedly non-tourist destination is the main rockabilly bar in Tucson located on 4th. The perfect grungy place to kick back with a PRB and a cheap shot of whiskey and listen to some live music while examining an ever-changing assortment of tattoos. Apparently the food is pretty good for a bar as well.
Luxor Cafe (3699 North Campbell Avenue) -
A middle-eastern restaurant and more interestingly Tucson's main hooka bar where you can lounge on low chairs, drinks some tea, have a piece of baklava and relax with some Guava-flavored, or any of dozens of other flavored, hooka after dinner but before you go get cocktails.
The Loft Cinema (3233 East Speedway Boulevard) -
A two screen art movie theater in which the upstairs theater has couches. They also serve beer and wine. So check out an old, obscure film on a relaxing night so you have something to chat about over cocktails.
Let me know if you have any other places you like there!