Cleveland For One Night
My wife and I will be in Cleveland for a conference between 10/1 and 10/4. Our only "for sure" free night is Wednesday, 10/1. We'll be staying at the Renaissance Cleveland downtown, and will have one guest with us on Wednesday for dinner.
We like high end, easy eating food. Nothing too fancy and no pomposity. Flavor preferences are Italian/Mediterranean/Southwestern/California. (One of us doesn't like Asian and I'm an obedient spouse.) Good martinis and a good wine by the glass selection are required. Decent bread is also a good test for me. (Amateur baker.)
I was set to make a reservation at Lola (close to the hotel) or Lolita (sounds like more fun), but the reviews are decidedly mixed. We won't have a car, but a short/medium cab ride is not an issue. Neither is cost, but we're not looking for super-fine dining.
How about taking light rail public transit? It's the easiest trip you'll ever take. You can get to the the rapid without walking outside. From your hotel you'll walk through the mall at the bottom of the adjacent building. The rapid stops right at the door of the restaurant. It's actually less than you'd have to walk to get to many restaurants from their parking lots. You'll spend about 15 minutes on the train itself. I can't remember... I think it costs $1.75.
Shaker Square is a beautiful neighborhood - historic, charming... fire food and drink is one of the area's best restaurants. I always recommend the pork chop on these Chowhound threads. It really is phenomenal. But I recently had the fillet and the ribeye. They were both great so I can now confidently recommend them as well. I hadn't had either one in years. I'd fallen into a rut eating fire's fish. Obviously, I think highly of the fish, too. The last time I was there, I enjoyed a pasta dish. But really, get the pork chop or the ribeye or some fish.The chef really likes simple, homey desserts. The blueberry crisp is great. The bread is okay but don't pass on it. They serve it with phenomenal olive oil. Add a little salt to the oil and dip generously. You won't be disappointed.
Bar Cento is actually also accessible by rail. Alternately it's only 1.7 miles so you could cab it. On October 1st Bar Cento will host a beer tasting dinner. 8 courses paired with 8 beers. Even though it's a big menu, Bar Cento is not fancy. No trace of pomposity whatsoever.
After the dinner, and perhaps during, Bar Cento will serve their regular menu. When the kitchen is on its game, the food at Bar Cento is as good as any in the area. (Just ignore the bread.) The regular menu is generally simple food, prepared well from conscientiously sourced ingredients. Some of the best items are the pizzas - the sugar onion or the bacon and potato for instance. The BONE IN skate wing appetizer is also great. The atmosphere is casual, dim and loud.
Fire Food & Drink
13220 Shaker Square, Cleveland, OH 44120
1948 West 25th Street, Cleveland, OH 44113
I would suggest Osteria downtown. http://osteria.us/
If you end up having additional free nights, I would definitely check out Lola. Great food, great wine list, beautiful restaurant. But reservations are a must; during the week you can often get reservations for dinner that night without too much difficulty, but you might have to be a little flexible with time.
If you like pork - Lola is still your best bet. I have enjoyed every meal I've had there, and I've had several. Though it is high end, it isn't at all stuffy. Lolita is also a lot of fun and the pulled pork pizza is awesome. The bread service is so-so - but the pizzas are fabulous - Chef Matt Harlan has the Neapolitan certification. You can make a dinner out of all of the appetizers (which is easy to do because they are fabulous), or get some pizzas and share some entrees - the menu is very flexible. Make sure to get the creamed corn and the cheesy polenta while you are there! There is a lengthy thread on Lola and Lolita on EGullet with lots of photos: http://forums.egullet.org/index.php?s...; you can make up your own mind!
If you do decide to go elsewhere, I agree with Stuart that fire and Bar Cento are outstanding, each in their own way, though Bar Cento might be a little loud for your taste.
Another outstanding choice near to downtown is The Flying Fig, in Ohio City. Since it is right across the street from Great Lakes Brewing Co., you can enjoy a wonderful beer before or after dinner! Also in that same neighborhood (Ohio City) is Momocho, which serves superb Nuevo Latino cuisine in a super casual atmosphere.
And after dinner - be sure to visit the Velvet Tango Room for a handcrafted cocktail and delightful live music. VTR is easily reached by RTA train or cab from where you will be.
Flying Fig in Ohio City is a short cab ride from downtown. I haven't been in a while (moved from Cleveland last year), but it is fantastic usually.
I also love Momocho in Ohio City- also a short cab trip. "upscale" but very casual "modmex" food. On my last trip to Cleve in July, I ate there and it is as good as always.
I always like Blue Point Grill in the Warehouse district, but it gets mixed reviews.
If you venture out east, fire food and drink on Shaker Square is a great bet.