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Cuban Picadillo Stuffed Plantains

Cuban Picadillo Stuffed Plantains

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These picadillo stuffed plantains are the perfect marriage of authentic Cuban flavors with a sweet and salty vibe.

If I had to pick my absolute favorite flavor combination, sweet and salty would be it. These Cuban picadillo stuffed plantains hit that combination perfectly. As the plantains roast, their flesh caramelizes into sweet perfection, which is the perfect match for the saltiness of the picadillo. Sprinkling a little queso fresco over the top marries the whole thing together!

Plantains can be cooked in varying stages of ripeness, but this recipe specifically calls for yellow plantains that are starting to turn black (below). If they are totally black, they will lose their structure and become overly sweet while roasting. But plantains that are still green will never cook correctly using this method. They end up tough and stringy- trust me, I’ve tried!



These stuffed plantains call for my Cuban picadillo recipe, which I have previously posted. This is one of my all time favorite Cuban recipes and it comes directly from Joey’s family cookbook. I have included that recipe below but you can also find it here. It’s possible that the only improvement that can be made on that recipe is to serve it between perfectly roasted plantains.


The ingredients for the Cuban picadillo should all look familiar with the potential exception of two- vino seco and adobo con pimenta.


Vino seco is a dry golden cooking wine integral with Cuban cuisine. I have detailed some information about what this wine is and how to find it here. I definitely recommend it for that extra dose of Cuban flavor perfection! But if you absolutely can’t get your hands on any, substitute in white wine.


As for adobo con pimenta (adobo with pepper), this is a spice mix available in most major grocery stores. You can usually find it with the spices or in the Hispanic section. There are many brands, and the one I can most easily find here in Denver is Goya. You can find more information about adobo con pimenta here.

While I think this dish is great on it’s own, there are many side dishes to potentially pair it with! Try it with Cuban black beans, fried or mashed yuca, or a light avocado salad. And remember- if you have leftovers, one of the best things about Cuban style picadillo is that is absolutely better the next day!


Cuban Picadillo Stuffed Plantains

These picadillo stuffed plantains are the perfect marriage of authentic Cuban flavors with a sweet and salty vibe.

Course Dinner, Main Course
Cuisine Cuban
Keyword authentic, cuban picadillo, cuban recipes, golden cooking wine, stuffed plantains, vino seco
Prep Time 10 minutes
Cook Time 40 minutes
Servings 6 people


For the Plantains:

  • 6 ripe (yellow and black) plantains
  • 1/4 cup olive oil
  • 4 oz queso fresco

For the Picadillo:

  • 2 tbsp olive oil
  • 1/2 large yellow onion, diced (about 3/4 cup)
  • 1/2 red or green bell pepper, diced (about 3/4 cup)
  • 3 garlic cloves, minced
  • 1 8-oz can no-salt-added tomato sauce
  • 1 tsp adobo con pimienta
  • 1/2 tsp oregano
  • 1 tsp cumin
  • 1/2 tsp paprika
  • 1.5 lb 100% grass-fed ground beef (85% lean)
  • 1 bay leaf
  • 1/4 cup vino seco (or substitute white wine)
  • 1 5.75 oz jar pimiento stuffed manzanilla olives + 1/4 cup brine
  • salt and pepper to taste


Roast the Plantains:

  1. Preheat the oven to 400.

  2. With a knife, slit the plantain peel on each side and peel it like a banana, leaving it attached to the bottom.

  3. Rub each plantain with olive oil, and rewrap them as much as possible in the peel. This will keep them extra moist while baking! Place the plantains on a baking sheet.

  4. Roast plantains for 40 minutes.

Make the Cuban picadillo:

  1. In the meantime, Add olive oil to a large pot and heat over medium heat.

  2. Add onions and cook for about 1.5 minutes, until just starting to turn translucent.

  3. Add bell pepper and garlic and cook for another 2-3 minutes. You still want your vegetables to be crunchy and retain some of their texture.

  4. Lower heat to medium-low. Add tomato sauce, adobo con pimienta, oregano, and cumin. Cook until the sauce turns a deep red, stirring occasionally to keep from burning, approximately 10 minutes.

  5. Increase heat to medium again. Add ground beef and paprika and cook for another 10 or so minutes, until browned.

  6. Add bay leaf, vino seco, and olives + 1/4 cup of their brine. Cook for another 10 or so minutes, stirring occasionally.

Stuff the plantains:

  1. When the plantains have cooled somewhat, slit each one down the middle.

  2. Fill with picadillo and sprinkle with queso fresco.

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