Feature Image: Cuban Sandwich and crispy fries from Toasted Monkey, St. Pete Beach, Florida

I walk down the central artery of 7th Avenue in Tampa’s Ybor City neighborhood, looking for a suitable place to perch myself on a barstool and order one of the town’s signature dishes - the Cuban sandwich. It’s early enough, still plenty of sunlight in the sky and that’s good. It was an early morning and I’m seeking a fairly quiet space where I can simply eat and relax with a beer, and Ybor can get pretty noisy once the sun drops below the horizon.

I settle on Gaspar’s Grotto, a themed restaurant that pays homage to Tampa’s history as a hideaway for pirates. Specifically, this establishment is named for Jose Gaspar, the legendary Spanish buccaneer who reined terror on Florida’s west coast at the turn of the 19th century…maybe. Like Robin Hood, he may or may not have ever existed, except in the imaginations of storytellers and folklorists. But the mythology around Gaspar has grown over the past 100 years, and has spurned several restaurants and attractions that bear his name as well as the annual Gasparilla festival that draws over a million people to the area each January. The outdoor bar is pumping beach music through the speakers and although I want to be in the mood for it, it’s just not happening. Inside, the energy is quieter and at least to me, more enjoyable.

Cuban sandwiches are of course a regional favorite in Tampa. It is the cheesesteak to Philly or the lobster roll to Boston. Built with soft Cuban bread that is similar to a small loaf of Italian, it is layered with roast pork, sweet ham, Swiss cheese, dill pickle slices and mustard. It is then griddle pressed to form what sounds like little more than a warm ham and cheese sandwich. The Tampa variant contains Genoa salami as a tribute to the Italian immigrant population that worked in Ybor’s cigar factories in the 1800’s alongside the Cubans. It adds a bit more flavor, but there’s something else that makes it more delicious than a traditional deli sandwich. I can’t place it, but I plan to find out what it is.

The bartender hands me a menu, but I don’t need it. “I’ll take the Cuban, and whatever is good on tap.”

“Bud Light is good to me. I drink water and it gets me drunk, but I don’t know if that’s what you are looking for.” It’s not. A local pale ale is more my style.

Cuban Sandwich, Gaspar's Grotto, Ybor CIty, Florida

Gaspar's Grotto serves up Cuban sandwiches with local craft brew at the indoor bar, or outside on the patio with live music.

After a few moments, my dinner arrives. The sandwich is accompanied with steak fries, and looks…decent. The bread has been pressed flat and the melted cheese on both sides has cemented the thing shut. It’s the perfect meal to have while driving, really. Flattened to perfection, it can be held in one hand without any trouble. Nothing falls out into your lap. No mess, no fuss. The first bite is delicious, with the sweetness of the ham balancing out the bitterness of the beer that is disappearing at an alarming rate. I continue eating quickly, the bartender gone now and the stools along my side of the bar all empty. Any attempt at making conversation is impossible. It’s just as well. I’ve been up since 3:30, having to catch the early flight out of Boston to Tampa and I wouldn’t be good company, anyway.

The first and only time I have had had a Cuban sandwich prior to walking into Gaspar’s was a few years back. My son, probably 11 or 12 at the time, had watched a television episode that featured a food truck that sold only Cuban sandwiches and he wanted to give them a try. We roasted a pork shoulder and purchased the deli meats, Swiss cheese and pickles from the grocery store. We used whatever sub rolls happened to be on the shelf. What I can recall is making them, my son’s eyes wide with anticipation as he stacked the roast pork over the ham and salami, strategically placing each pickle slice as if the inside of the sandwich were some sort of jigsaw puzzle. Those were good times, when we enjoyed making new meals together as a family. Not anymore. Diagnosed with ulcerative colitis shortly thereafter, food has become his nemesis. He runs an endless gauntlet trying to figure out which foods will let him pass unscathed, and which will demand that a price be paid.

Now, in the empty bar I finish my dinner and decide to head back to the hotel. It was good, but I’m tired. Unfortunately, I’m here for work and morning will come quickly. It was a decent start to my search for the perfect recipe.

The next night is beautiful and I want to catch the sunset over the gulf, so I head out to St. Pete Beach. My planned destination is the Toasted Monkey, a beachside bar chosen simply because the name sounds full of possibility and inappropriateness. I arrive in the parking lot and realize that the restaurant is part of a Howard Johnson’s hotel. I thought that HoJo’s went out of business long ago, but there it was in front of me with the trademark peaked roof and 1970’s decor. I almost leave but I’m hungry and don’t feel like searching all over again.

The open-air bar is out back, right up against the beach and there’s live entertainment. It’s not as bad as the picture in my mind. “What can I get you?,” the bartender asks.

“Blue Moon and the Cuban sandwich.” The guitar player is strumming away and singing those easy-going, life is good songs that seem to be the staples in every beach town. People are here on vacation and having a good time, getting drunk and chatting away in groups. There’s not another lone traveler at the bar to strike up a conversation. Just me, and I’m not very good company.

Thankfully, my dinner arrives shortly and I can stop staring at my phone. This time, the sandwich retains its natural loftiness, having been spared the panini press. The roast pork is plentiful between the crispy bread and has, at least according to my crude taste buds, a near perfect level of mojo citrus flavoring and topped with thick sliced pickles for a flavor that just may end up a winner. The side of fries is deep fried to perfection and has that crispy coating on all sides that takes a little bit of magic to create. I’m glad I gave the Toasted Monkey a chance, but as I watch couples dancing between the tables or groups of friends becoming louder with each round of drinks, I know I don’t really belong here. At least not right now.

7th Avenue, Ybor City, Tampa, Florida

Cuban Sandwiches are a staple in Tampa, offered on almost all menus in Ybor City.

It’s the third night, and I’m starting to crave something different, but I wanted to go back to Ybor City and try an Italian eatery that seems pretty confident in their Cuban sandwiches, having painted the menu item in oversized lettering on the outside wall of the restaurant. Besides, maybe an Italian spin on Tamps’s signature handheld will be a bit different. Perhaps it will be heavy on the salami, which I like. As I walk in, I notice the empty tables. There are only a few other customers in the restaurant. I get a bad vibe, but again I already committed in my head to check it out and so I stay. I order the usual and it is unremarkable in every way. It also is significantly more expensive that my previous meals and came with no sides, just plenty of white space on the plate. I can only assume that the value for the entire menu is similar. The place was empty for a reason. I decide to eat quickly and beat feet. It was a bust.

Even though I have one more night in Tampa, I am finished with my search. I’ve already figured out what makes the perfect sandwich. In fact, I’m confident that I can do it better than anyone in Tampa.

The next week, over 1,000 miles from Florida, I return home from the grocery store with the necessary items. After marinating the pork loin overnight in mojo seasoning, it gets roasted on the grill. Not the recommended technique, but it will do. The bread consists of small Italian loaves. The Swiss cheese is not really cheese. It’s a non dairy concoction of ingredients that resembles fondue. Again, not the preferred method but necessary this time around so as not to aggravate my son’s gut, which is firmly in charge of what can and cannot be consumed. Dairy products are definitely off the menu.

“Cuban sandwiches tonight, buddy,” I tell him. He smiles, not particularly because he craves them but because it kindles the memory of the first time we made them together, back when he was younger and even the process of making a simple meal was just a bit more extraordinary.

“Cool.” It’s nonchalant, but I can tell that it really is just that - cool.

We stack the salami, ham, and roast pork slices on top of each other like it’s an engineering project, then spread the cheese-like sauce and flatten it in the frying pan with a bacon press. We make a stack of four, one for everyone in the family. Eating all together as a family doesn’t happen as much as it should, but schedules and determination allowed it happen tonight. With a large bag of chips in the middle of the table, we all grab a handful and start digging in. The bread is a bit tough, and the fondue sauce a bit tangy, but it doesn’t matter a bit. It is definitely the most delicious Cuban sandwich - ever.

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