This post is the second in a series of four that outline the restaurants and bars I’ve visited over the past months. The posts will be organized by Latino, Caribbean, and Spanish dining; casual dining; casual upscale dining; and bars and breweries. I will continue to return to these posts and update them as I visit more places – there are many many more to be savored! And, I’d love if you left any recommendations you might have in the comments section.My favorite type of casual eatery down here in Florida is the kind that serves up heaps of fried gator tail, conch fritters, and a relaxed, beachy vibe. The Oasis, a place I wrote about here, is one of those places. With its tiki huts and waterfront location, the Conch House also qualifies.
Their Reggae Sunday is legendary in the area, and the food is a perfect match for the chilled-out tunes. You of course can’t go wrong with the meaty gator tail…
Or the conch fritters
Entrees are also good, like the nut-crusted grouper salad…
Or the blackened wahoo sandwich (Phil’s favorite). Don’t miss Reggae Sunday from 3-7pm; also perfect for a lazing away the afternoon with a margarita or a cold one, any day of the week. http://www.conch-house.com 57 Comares Ave, St Augustine, FL 32080 (904) 829-8646 
Le Café is an often overlooked diner just outside of the historic district on US1. Lunches of French melts with au jus or quiche are served up by the French owner’s daughter. Don’t miss the beignets and coffee. 415 S Ponce De Leon Blvd, St Augustine, FL 32084 (904) 826-1034
Another diner just behind Flagler, Georgie’s Diner offers all the classic diner staples with a Greek twist in one of the coolest buildings in town.
I tried the enormous Greek sampler with moussaka, grape leaves, spanokopita, and Greek salad. There was enough left over for two more lunches!
The chicken fried steak with brown gravy, a fried egg, hash browns, and a biscuit was equally belly-busting, but oh-so-Southern.
The classic corned beef hash was also, of course, huge and delish.
Lighter fare is also available – my dad ordered a chicken wrap with sautéed Greek potatoes. But it couldn’t compare to the rest of our calorie bombs. Always busy and bumpin’ for weekend brunch. http://www.georgiesdiner.com/ 100 Malaga St, St Augustine, FL 32084 (904) 819-9006 
Gypsy Cab Co. is a local favorite. I found it didn’t quite live up to all the hype. The menu lacks focus, portions were ridiculously sized, and everything seemed smothered in cheese or cream yet lacked proper seasoning. Chicken and chorizo with black beans and rice was a jumbled, soupy mess.
The chicken enchiladas were exactly what you would expect.
And, the four-nut crusted chicken was nice and crisp before they smothered it in under-seasoned cream sauce. And, hey, what about the sauce for the pasta? It was literally boiled pasta tossed with some chopped parsley.
My dining companions were very happy, for what it’s worth. Next time I’ll order a sandwich. Or go when I have a hangover and want melted cheese smothering my food beyond recognition. http://www.gypsycab.com/ 828 Anastasia Blvd, St Augustine, FL 32080 (904) 824-8244 
I’ve been to Madre’s on picture-perfect Aviles Street more than any other place in St. Augustine, and would definitely consider it my local haunt. They offer California cuisine in a festive surfer atmosphere.
It’s the perfect feel-good place for happy hour drinks Thursday, Friday, and Saturday, when Miller High Life drafts are only $1! Warm housemade chips, salsa, and pickled carrots are complimentary whether you only come for drinks or plan to stay for a meal.
The specialty is Baja fish tacos, and along with the chips and salsa, one portion of tacos is enough to share. If you ask nicely, the chef will even split one order into two plates. 8 Aviles St, St Augustine, FL 32084 (904) 823-1371 
The Spanish Galleon Café wins awards for their freshly-brewed coffee. Nathan’s hot dogs are on the menu, you can get breakfast all day, and their special is a steak sandwich. Stop in for a coffee and a snack in the hours between lunch and dinner. 210 Saint George St, Saint Augustine, FL 32084 (904) 824-1610 
If you’re a St. Augustine native, you might want to skip my review of O’Steen’s. This place is the most often and highly recommended restaurant in town, and is always swarming with diners willing to wait up to two hours for a table. I tried eating here twice before actually making it happen. Once the wait was over an hour at 2:00pm in the afternoon! Well, if I’m going to wait that long, the food better be darn worth it. I’m sorry to say that it didn’t live up to my expectations. I completely understand that O’Steen’s is a nostalgic place for locals who have eaten there since they were kids, and I also understand that I’m probably not exactly the target market for the place. It was filled with old timers, families, and gullible tourists when I went. Honestly, they don’t give a hoot if I ever go back. I was looking forward to their Minorcan chowder, a tomato-based soup made with the native datil pepper that’s a local specialty in many restaurants. I couldn’t get past the overwhelming taste of dried thyme.
Their fried shrimp is praised up and down by seemingly every single person who’s ever dined here. It was good, but I wasn’t doing cartwheels around the dining room from excitement or anything. And, I don’t know about you, but I really enjoy a cold beer when I eat fried food. You’re out of luck here – O’Steen’s is a dry establishment.
The best parts of the meal were the okra that came as a side with the shrimp, and the hushpuppies.
The fried scallops, again, were good. I mean, they were fried scallops, and fried scallops are good. But the fries that came with them were obviously frozen and not made in-house. Everything came with two sauces. One was a housemade datil pepper hot sauce, which was basically a chunky tomato ketchup with some datil pepper in it, and wasn’t spicy at all. The special house sauce consisted of mayonnaise, ketchup, Worcestershire sauce, and some of that datil pepper hot sauce.
Please do not forget cash if you dine at O’Steen’s – they don’t take cards and only accept local checks. We didn’t have enough to cover our bill, and the nearest ATM was out of order, so one of my dining companions spent 20 minutes driving around looking for another machine, while the rest of us waited patiently at our table without a beer or glass of wine to bide the time. By all means, please dine at O’Steen’s and form your own opinion of the place. It’s obviously got something going for it, judging by the line out the door. 205 Anastasia Blvd, St Augustine - (904) 829-6974 
On a much more upbeat note, Florida Cracker Café is another one of those places offering fried gator tail and conch fritters in a fun, unpretentious setting right on pedestrian St. George Street. During happy hour, I’ve enjoyed 6 Amber Bocks for $12, including tip. There’s live music in the courtyard – I especially like the Skinny Lizards who play every Wednesday. Stop in for a beer and a bite and take a break from all that sightseeing under the hot Florida sun. http://www.floridacrackercafe.com/ 81 Saint George St, St Augustine, FL 32084 (904) 829-0397
And don’t forget about Stir it Up on St. Augustine Beach, which I wrote about here!Later this week: St. Augustine Round-up Pt 3: Casual Upscale Dining.
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