Roasted Tomato Grilled Cheese with Basil Pesto

This roasted tomato grilled cheese sandwich, tucked between two crusty pieces of Parmesan sourdough bread with a smear of basil pesto, is inspired by Alpino Vino — North America’s highest elevation restaurant (11,966 feet) in Telluride, Colorado.

Alpino Vino Roasted Tomato Grilled Cheese Recipe with Salad

We recently visited the resort for a ski vacation, and lunch at Alpino Vino was a wonderful treat. The restaurant overlooks the beautiful snow-capped mountains and down into the valley.

Boasting sweeping views of the Wilson Range, Alpino Vino sits on the site of a historic mining claim. The restaurant’s inspiration comes from the Northern Italian Alps that border Switzerland, and the birthplace of Chef Nico Peccedi, who hails from Bormeo.

Inside, a wood-burning fireplace roars in the cozy dining room, which boasts rustic wooden tables draped with fur on each seat. If the weather is nice, enjoy a spot on the beautiful outdoor deck which overlooks the valley, complete with daybeds, sheepskin blankets and European teak furniture. 

Since the restaurant has no gas lines, Chef Peccedi and his team cook his Northern Italian specialties on a portable induction burner. Signature dishes include menu items such as Insalata Caprese, Lasagna Bolognese, Lobster Gnocchi, and a variety of gourmet Panini sandwiches.

Although the Wagyu Panino made with roasted Snake River Farms Wagyu beef and crispy onions looked tempting, we went with their signature roasted tomato grilled cheese. All panini are served with your choice of organic Tomato-Gorgonzola Soup or Insalata Alpino.

We enjoyed this with a glass of 2019 Daou Vineyards Reserve Chardonnay (Paso Robles), but they also have an impressive list of Italian wines by the glass, such as a 2016 Brunello di Montalcino (Piancornello, Tuscany, Italy) or a 2019 Barbaresco, (Castello di Neive, Piedmont, Italy).

How to make a Roasted Tomato Grilled Cheese Sandwich

To make this Roasted Tomato Grilled Cheese recipe, you’ll need some good quality Artisan sourdough bread. For the filling, I recommend a double-cream Colorado cheese such as Cashmere Double Cream Organic Brie Cheese or Haystack Funkmeister double cream washed-rind cheese.

Finish the sandwich with some basil pesto smeared on both sides, soft roasted or grilled tomatoes, and a handful of fresh arugula. Serve with a creamy homemade tomato soup.

More Easy Sandwich Recipes:

Alpino Vino Telluride

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Alpino Vino Grilled Cheese with Roasted Tomatoes

Roasted Tomato Grilled Cheese with Basil Pesto

Recipe by Jason Hill –
This roasted tomato grilled cheese sandwich, tucked between two crispy pieces of artisan Parmesan sourdough bread, is inspired by Alpino Vino — North America’s highest elevation restaurant (11,966 feet) in Telluride, Colorado.
5 from 1 vote
Prep Time 15 minutes
Cook Time 40 minutes
Total Time 55 minutes
Course Main Course
Cuisine American, French
Servings 2


  • 4 slices Artisan sourdough bread

Parmesan crust

  • 4 tablespoons softened butter
  • 4 tablespoons finely grated Parmesan cheese
  • 2 cloves garlic minced

Roasted Tomatoes

  • 2 Roma tomatoes sliced into thick rounds
  • 2/3 cup aged balsamic vinegar
  • 1/3 cup extra virgin olive oil
  • 1 tablespoon minced garlic or garlic-shallot puree
  • 10 fresh basil leaves, minced


  • 6 tablespoons basil pesto store bought or homemade
  • 2 cups Arugula leaves
  • 4-6 slices double-cream cheese enough to cover two slices of bread


  • Make the Parmesan butter by mixing together the butter, Parmesan and minced garlic. Set aside.
  • Make the roasted tomatoes by tossing the sliced tomatoes with the balsamic vinegar, olive oil, basil and seasoning. Marinate for 1 hour (to overnight) in the refrigerator. Roast on a pan at 375 F for about 30 minutes, or until nice and soft. Alternatively, grill over high heat for 10 minutes. Set aside for the sandwiches.
  • Prepare the sandwiches by buttering both sides of the sourdough with the Parmesan butter. Add additional grated Parmesan to the butter if desired.
  • Flip the bread over and smear basil pesto generously on the other sides of the bread. Layer one slice with thinly sliced brie to cover the sandwich. Top with the roasted tomatoes, and then arugula leaves to your liking.
  • Cover with the other slice of bread, making sure butter sides are out. Grill on a hot skillet, or in a panini grill until nice and crusty on both sides, and the cheese is nice and melted.
  • Serve with a hot bowl of tomato soup and glass of chardonnay.
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For the filling, I recommend a double-cream Colorado cheese such as Cashmere Double Cream Organic Brie Cheese or Haystack Funkmeister double cream washed-rind cheese.
Keyword brie, pesto, sandwich, sourdough, tomatoes
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AboutJason Hill

Hi, I’m Jason Hill, host of YouTube’s “Chef Tips” series. I graduated from culinary school in 1998, and gained my experience working the lines in Southern California. I launched my cooking videos in 2007. I love sharing quick and easy recipes that get people back in the kitchen.

5 from 1 vote (1 rating without comment)

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