For decent Cuban food, in Key West at least, you need real Cuban bread, which looks and tastes like floppy supermarket "French bread." French bread in France is crisp and hard on the outside and heavily aerated with a rough texture inside. In the US of A, French bread is a long pale loaf with a soft spongy interior. I'm not going to elaborate on what kind of a baking blasphemy produces an "English" muffin.
A three-dollar Cuban breakfast, cafe con leche with pan con queso at Five Brothers Deli on Ramrod Key, a staple Keys breakfast easily replicated at any of a number of Cuban delis in Key West- Seven Days, Kims Kuban, Little Jon's, Five Brothers ( the original store), Jeanas Courthouse, and on and on. A con leche with as many sugars as your teeth can stand along with a slice of Cuban bread filled with American cheese (Swiss if you're a wuss), toasted, and you're good till lunch. A con leche is just an abbreviated cafe con leche and is nothing more complicated than a cafe latte, as sold in Starbucks for three times the price.
A "Cuban mix" is Cuban bread with layers of cheese, roast pork, ham and pickles wedged between mustard and mayo and then squashed in a sandwich press which makes the whole thing flat, smooth and warm. You order thusly:" A Cuban mix, all the way, and a con leche with one." All the way gets you all the ingredients on offer including a smear of mayo and mustard. On the sandwich that is; "with one" gets you the appropriate number of sugars. If you're a Conch you need at least 5, possibly 8 in your con leche.
For dinner expect pork or pork, roast or fried (!) possibly shredded (ropa vieja), ground beef with olives (picadillo), or you could deviate from the favorite Cuban meat and go with flank steak served with a ton of lightly grilled onions on top. There are of course your wussy alternatives: grilled chicken or fish for those that can't digest fried pork chunks washed down with sangria and heavily buttered chunks of Cuban bread. Accompaniment is always rice and beans, separate or mixed (moros y cristianos), and as I'm not overly fond of black beans all the time, I try to see if I can get red beans, garbanzo beans, white (navy) beans or Lima beans depending on where I am eating out. This is not your average nouvelle cuisine large plate- tiny portions fare offered up in suburban American. Eating Cuban is a robust rough and tumble, napkins at the neck and stout cutlery to fight back the waves of food.
A word about plantains. These are NOT bananas even though they look like them, and conchs like to call them bananas to confuse lily white Northerners. They are a (relatively) sugar-free starch and taste foul uncooked. Plantains can come hard fried and served sprinkled with salt (tostones), 
which, along with some ketchup make an excellent appetizer, or soft fried in oil and they end up looking slimy and brown and are utterly delicious, like sweetened, sticky bananas.
which, along with some ketchup make an excellent appetizer, or soft fried in oil and they end up looking slimy and brown and are utterly delicious, like sweetened, sticky bananas.In my opinion a side of these things do away with the need for a dessert but if you figure how much sugar your average Cuban consumes you'll understand why you can always have flan, a cream caramel indistinguishable from the Mexican variety. Better is the natilla, a soft vanilla flavored pudding often sprinkled with a little ground cinnamon. Sometimes, if my wife isn't looking I can order a tres leches, three milk pudding layered and sticky and a heavenly reminder of imprisonment in English boarding school. Then they pour you into a wheelbarrow and roll you home, stuffed like a fois gras goose.
Do not make the mistake of assuming Cuban food (as served in the Keys and Miami- God knows what they eat on the island itself, fresh air sandwiches if the propaganda is to be believed) is anything other than a minor variant on general Caribbean rice-meat-beans, cooking. It is not Mexican, in that its not sauced or spicy. It has tons of variants with adherents to each variation, and other cultures get mixed in like this orange colored ("Spanish" style) rice made with tomato sauce at Coco's Cantina on Cudjoe Key when the daily special was $9 beef stew.
Notice the bowl of black beans, quite delicious actually, stewed with onions and served with a spoon. A Cuban or a Conch would make a hole in the rice and spoon in the beans to make their own "Christians and Moors" mixture of black and white. I just used the spoon supplied in place of the fork. The stew was so tender it didn't need a knife. 
And in the end you need a decent motorcycle, any motorized two wheeler, not necessarily a Triumph Bonneville, to get there, lacking a wheelbarrow to get you home.
