Cuban Sandwiches are a new fascination of mine. I didn’t have one up until a couple months ago, and instantly I fell in love with the flavors. I’d been making a traditional Cuban sandwich for a while using an adaptation of one of Tyler Florence’s recipes & my family seriously can’t seem to get enough of them.
You all know that I also have a deep adoration for grilled cheese sandwiches. They’re just pure love with their perfectly toasty bread & melty cheese. So, I decided to combine a traditional Cuban sandwich with a grilled cheese – and while I completely understand that this combination has immediately un-traditionalized the Cuban sandwich…. I’m totally ok with that. And I think that after one taste (heck, even one look!) of this deliciousness, you will totally be ok with it too.
So no emails telling me that you’re Cuban great-grandmother says this is not the traditional way of making this – I get that already! This is a crossbreed so to speak, and an outstanding one at that. With the flavorful & tender slow roasted Cuban pork, thinly sliced ham, 2 thick slices of Swiss cheese on each sammich, & the sourdough bread toasted to perfection in butter in a skillet… you can’t go wrong with this.
So, let’s do this already. I know you wanna. Because seriously, with something this darned delectable – how could you not?
The first step is the pork. Here’s what you need for it:
I’ve gotta take a quick moment to warn you for a moment about how fabulous this pork roast is. You’ll be swatting your own hand away from it once it’s done slow roasting because it’s just that good. Like – really, really good. Really, really, really, really good. Get the picture? Oh my….
Tie a 1.5 pound pork roast with cooking twine in 4 places – sort of like a tic tac toe board. This will keep the pork together while you cook it. Season it liberally with garlic salt, pepper, & oregano.
In a dutch oven, pour enough oil into the bottom to cover – about a 2 count. (You can also use a slow cooker if you like, instructions in printable recipe at bottom of post) Place about 6 cloves of garlic into the oil that you’ve gently smashed with the backside of a chef’s knife along with 1/4 teaspoon of crushed red pepper. Heat the oil on medium heat & sauté until you’ve achieved a light toasty color – as the oil warms, the garlic & red peppers will infuse the oil with flavor.
Add the pork into the middle of the dutch oven. Surround by one large onion, sliced into half rounds. Sear the pork roast for a couple minutes on each side to achieve a little crust going on. Pour in 1-1/4 cups of orange juice, 1 large lime juiced, 1 cup low-sodium chicken broth, & 3 bay leaves.
Cover your dutch oven, & place in the oven. Cook at 300 degrees for 2 to 2.5 hours – gently flipping halfway through.
Let the pork roast cool until lukewarm before removing the twine & slicing into thin slices. Try not to eat all of the pork because it’s sooooo very yummy!! Save the drippings inside of the pan if you’d like to have an au jus to serve along side. Just add 1 cup of orange juice & 1/2 cup of water (or chicken broth) into the pan, & cook on low – scraping the bits off the bottom while you’re prepping the Cuban Melts.
Now, for the sandwiches. Traditionally, Cuban sandwiches have sliced dill pickles on them, & you can buy those super awesome sliced dill pickles just for sandwiches. You can also use chopped pickles (sometimes I do this if I don’t have any sandwich sliced pickles on hand like in the pictures) – and some people even like relish or bread n’ butter.
Now…. It’s time to assemble your melts!
I used fresh sourdough bread from my local bakery for this – but you can buy sourdough at any grocery store.
Spread dijon mustard on the insides of each slice of bread. Place a semi thick piece of swiss cheese on each slice of bread over the dijon mustard (I had the deli slice my swiss cheese on 2). Now, atop one of the dijon/swiss coated pieces of bread, lay a slice or 2 of pork followed by the pickle of your choice – and then several slices of very thinly sliced ham.
Place the top piece of bread (with the dijon & cheese) on top making your sandwich.
Melt a couple tablespoons of butter in a skillet or griddle & cook the sandwiches on each time using a heavy press to press them down. I use a cast iron press, but if you don’t have one – use a heavy skillet or even aluminum foil covered bricks.
Serve with the au jus (if desired).
Man, these babies are SOOO YUMMY!!
- 6 cloves of garlic, lightly smashed with the back of a chef's knife
- ¼ teaspoon red pepper flakes
- 2-3 counts of olive oil
- 1.5 pound pork roast (I used a sirloin)
- garlic salt
- 1 medium to large onion, sliced
- 1.5 cups orange juice
- 1 large lime, juiced
- 1 cup low-sodium chicken broth
- 3 bay leaves
- ½ pound of thinly sliced ham
- dijon mustard
- Sliced dill pickles
- 12 to 18 slices of Swiss cheese (depending on if you make 6 or 8 sandwiches, 2 per sandwich)
- sliced sourdough bread
- Preheat your oven to 300 degrees.
- In a dutch oven, place 2-3 counts of olive oil in the bottom, enough to cover the bottom. Add the red pepper flakes & lightly smashed garlic cloves. Cook on low/medium until lightly browned & fragrant.
- Using twine, wrap the pork roast in 4 pieces - sort of like a tic tac toe board. Season liberally with garlic salt, pepper, & oregano. Place into the center of the dutch oven over the garlic. Add the onions around the outside of the pork. Sear on each side for a couple minutes until lightly browned. Pour in the orange juice, lime juice, chicken broth, & add the bay leaves. Place the top on the dutch oven & cook in the oven on 300 degrees for 2 to 2.5 hours.
- After the pork is cooked, let it cool to room temp before slicing. Reserve the drippings for au jus if desired (instructions to follow).
- Spread dijon mustard on the insides of each slice of bread. Place a semi thick piece of swiss cheese on each slice of bread over the dijon mustard (I had the deli slice my swiss cheese on 2). Now, atop one of the dijon/swiss coated pieces of bread, lay a slice or 2 of pork followed by the pickle of your choice - and then several slices of very thinly sliced ham.
- Place the top piece of bread (with the dijon & cheese) on top making your sandwich.
- Melt a couple tablespoons of butter in a skillet or griddle & cook the sandwiches on each time using a heavy press to press them down. I use a cast iron press, but if you don't have one - use a heavy skillet or even aluminum foil covered bricks.