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Cuban Sandwich with Tomatoes

Making sandwiches can be fun, especially when you combine your favorite foods. Delicious with fresh Lady Moon tomatoes! Make these ahead of time for large gatherings.
Prep Time 20 mins
Cook Time 6 hrs
Total Time 12 hrs 20 mins
Servings 8 People


  • 1-3 pounds Boneless pork shoulder
  • To taste Salt & pepper
  • 1 Tbs Ground cumin
  • 1 Tbs Dried oregano
  • 2 Large Tomatoes quartered
  • 2 Tbs Olive oil
  • 4 Cloves Garlic peeled and gently smashed with the side of your knife
  • 1/4 Tsp Crushed red pepper flakes
  • 1 Medium Onion sliced
  • 1 Cup Fresh orange juice
  • 1 Lime juiced
  • 1 Cup Chicken broth
  • 2 Bay leaves
  • 8 Cuban bread rolls
  • 3 Tbs Dijon mustard
  • 16 Slices Swiss cheese
  • 8 Slices Bread and butter pickles
  • 16 Slices Ham
  • To taste Salt & pepper
  • Olive oil


  • For the Cuban pork: Heat a large skillet on high, add the olive oil, garlic and onion.
  • Sauté for 3 minutes, stirring to make sure it doesn't burn.
  • Add the pork and braise on each side.
  • Season with the salt, pepper, cumin and oregano.
  • In a crock-pot, add the chili flakes, orange juice, lime-juice, chicken broth, bay leaves, tomatoes and pork.
  • Cook on low for 5-7 hours, until tender, make sure to reserve the broth.
  • To prepare the sandwiches: split the bread in half and layer with mustard and pickle.
  • Add the cheese.
  • Top with pork, ham, onions and tomatoes.
  • Add another layer of cheese.
  • To cook the sandwich put in a sandwich grill, brush with the broth from the pork and gently close the lid down and cook for 4-7 minutes.
  • Serve immediately.
  • If you are grilling use a heavy skillet; top with a heavy weight to press the sandwich down and cook on each side for 3-6 minutes until the bread is crispy and the cheese is melted.